To Boot New York - Men's Boots

Men's boots by To Boot New York. There's something particularly satisfying about boots, proper footwear, especially when there's work to be done or if it's cold.

Prices correct at time of writing - subject to change

Men's To Boot New York 'Aaron' Oxford

$325

Perforated trim offers added sophistication to a handsome cap-toe oxford crafted from soft, burnished leather. Color(s): black, tan. Brand: To Boot New York. Style Name: To Boot New York 'Aaron' Oxford (Men). Style Number: 261894. Available In Stores.
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Men's To Boot New York 'Aaron' Oxford, Black

$325

Perforated trim offers added sophistication to a handsome cap-toe oxford crafted from soft, burnished leather. Color(s): black, tan. Brand: To Boot New York. Style Name: To Boot New York 'Aaron' Oxford (Men). Style Number: 261894. Available In Stores.
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Men's To Boot New York 'Altman' Sneaker

On sale - now $199.96 - was $299

Buttery soft calfskin forms a sleek sneaker topped with a pair of smart straps. Color(s): black. Brand: To Boot New York. Style Name: To Boot New York 'Altman' Sneaker (Men). Style Number: 746650.
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Men's To Boot New York 'Ashton' Driving Shoe

On sale - now $221.25 - was $295

Bold contrast stitching livens up a casual driving shoe shaped from soft suede. Color(s): soft black, soft brown. Brand: To Boot New York. Style Name: To Boot New York 'Ashton' Driving Shoe. Style Number: 969764.
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Men's To Boot New York 'Ashton' Driving Shoe, Black

On sale - now $221.25 - was $295

Bold contrast stitching livens up a casual driving shoe shaped from soft suede. Color(s): soft black, soft brown. Brand: To Boot New York. Style Name: To Boot New York 'Ashton' Driving Shoe. Style Number: 969764.
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Men's To Boot New York 'Barbados' Fisherman Sandal

$275

Designed for pure comfort, a breathable fisherman sandal crafted in rich Italian leather features a hook-and-loop closure and a laser-etched map of Manhattan at the sole. Color(s): trapper cognac. Brand: To Boot New York. Style Name: To Boot New York 'Bar
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Men's To Boot New York 'Benton' Wingtip

$398

Rich burnishing adds to the vintage vibe of a low-profile wingtip shoe featuring a leather sole with laser-etched map detailing of Manhattan. Color(s): brown, softy sigaro, trapper cognac. Brand: To Boot New York. Style Name: To Boot New York 'Benton' Win
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Men's To Boot New York 'Brandon' Cap Toe Oxford (Nordstrom Exclusive)

$395

Exquisitely burnished Italian leather forms a handsomely crafted oxford featuring sleek lines and no-nonsense design to achieve understated elegance. Color(s): black, cognac. Brand: To Boot New York. Style Name: To Boot New York 'Brandon' Cap Toe Oxford (
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Men's To Boot New York 'Brandon' Cap Toe Oxford- Black (Nordstrom Exclusive)

$395

Exquisitely burnished Italian leather forms a handsomely crafted oxford featuring sleek lines and no-nonsense design to achieve understated elegance. Color(s): black, cognac. Brand: To Boot New York. Style Name: To Boot New York 'Brandon' Cap Toe Oxford (
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Men's To Boot New York 'Brennan' Wingtip Boot, Brown

On sale - now $337.5 - was $450

Richly burnished leather lends an antique feel to a sharp boot clad in classic wingtip paneling. Lacing grommets switch to hooks at the shaft to further the vintage appeal. Color(s): cognac. Brand: To Boot New York. Style Name: To Boot New York 'Brennan'
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Men's To Boot New York 'Burns' Double Monk Strap Shoe

$450

Wingtip paneling adds sharp texture to a bold monk strap shoe fashioned from burnished calfskin. Color(s): tan. Brand: To Boot New York. Style Name: To Boot New York 'Burns' Double Monk Strap Shoe (Men). Style Number: 746654.
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Men's To Boot New York 'Cadiz' Braided Leather Flip Flop, Brown

$165

Rich, earthy leather is woven into the wide straps that top the foot in a casual, rubber-soled flip-flop. Color(s): dark brown, vitello dark brown. Brand: To Boot New York. Style Name: To Boot New York 'Cadiz' Braided Leather Flip Flop. Style Number: 2437
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Men's To Boot New York 'Campbell' Monk Strap Slip-On

$395

A sleek plain toe box fronts a classic slip-on topped with a single monk-strap closure. Color(s): black, brown. Brand: To Boot New York. Style Name: To Boot New York 'Campbell' Monk Strap Slip-On. Style Number: 617050.
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Men's To Boot New York 'Campbell' Monk Strap Slip-On, Brown

$395

A sleek plain toe box fronts a classic slip-on topped with a single monk-strap closure. Color(s): black, brown. Brand: To Boot New York. Style Name: To Boot New York 'Campbell' Monk Strap Slip-On. Style Number: 617050.
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Men's To Boot New York 'Carter' Apron Toe Derby

On sale - now $296.25 - was $395

Lustrous calfskin leather shapes a handsome derby cast in a sharp, modern silhouette. Color(s): black, marrone. Brand: To Boot New York. Style Name: To Boot New York 'Carter' Apron Toe Derby (Men). Style Number: 743920.
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Men's To Boot New York 'Clarkston' Chukka Boot

$350

Soft suede forms a lightly structured chukka boot in a lean silhouette. Color(s): cigar. Brand: To Boot New York. Style Name: To Boot New York 'Clarkston' Chukka Boot. Style Number: 684282.
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Men's To Boot New York 'Cornell' Chukka Boot

On sale - now $298.5 - was $398

Antiqued leather defines a high-shine chukka boot with eye-catching appeal. Color(s): cognac, trapper black, trapper brown. Brand: To Boot New York. Style Name: To Boot New York 'Cornell' Chukka Boot (Men). Style Number: 744302.
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Men's To Boot New York 'Duke' Wingtip

$450

Handsomely burnished calfskin forms a classically crafted wingtip steeped in rich style. Color(s): parmadoc nero. Brand: To Boot New York. Style Name: To Boot New York 'Duke' Wingtip (Men). Style Number: 743912.
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Men's To Boot New York 'Duke' Wingtip, Brown

On sale - now $337.5 - was $450

Handsomely burnished calfskin forms a classically crafted wingtip steeped in rich style. Color(s): brown. Brand: To Boot New York. Style Name: To Boot New York 'Duke' Wingtip (Men). Style Number: 743912 1.
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Men's To Boot New York 'Erik' Venetian Loafer

On sale - now $199.9 - was $325

Apron toe construction forms a sleek loafer cobbled from handsome calfskin leather. Color(s): vitello marrone brown. Brand: To Boot New York. Style Name: To Boot New York 'Erik' Venetian Loafer. Style Number: 956444.
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Men's To Boot New York 'Farley' Sneaker

$350

A cool street sneaker set on a sporty contrast sole is crafted in grainy Italian leather with superb style. Color(s): plonge brown, plonge nero. Brand: To Boot New York. Style Name: To Boot New York 'Farley' Sneaker (Men). Style Number: 866217.
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Men's To Boot New York 'Farley' Sneaker- Brown

$350

A cool street sneaker set on a sporty contrast sole is crafted in grainy Italian leather with superb style. Color(s): plonge brown, plonge nero. Brand: To Boot New York. Style Name: To Boot New York 'Farley' Sneaker (Men). Style Number: 866217.
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Men's To Boot New York 'Felix' Plain Toe Suede Derby

On sale - now $243.75 - was $325

Supple suede forms a handsome derby steeped in vintage appeal and versatile style. Color(s): black leather, black suede, tan. Brand: To Boot New York. Style Name: To Boot New York 'Felix' Plain Toe Suede Derby (Men). Style Number: 261867. Available In Sto
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Men's To Boot New York 'Felix' Plain Toe Suede Derby, Brown

On sale - now $243.75 - was $325

Supple suede forms a handsome derby steeped in vintage appeal and versatile style. Color(s): black leather, black suede, tan. Brand: To Boot New York. Style Name: To Boot New York 'Felix' Plain Toe Suede Derby (Men). Style Number: 261867. Available In Sto
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Men's To Boot New York 'Fiji' Leather Slide Sandal

$195

Straps of rich calfskin leather top off a handsome sandal with understated appeal. Color(s): vitello marrone, vitello nero. Brand: To Boot New York. Style Name: To Boot New York 'Fiji' Leather Slide Sandal (Men). Style Number: 866414.
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Men's To Boot New York 'Flanders' Double Monk Strap Shoe

$350

Double-monk styling adds vintage appeal to a soft Italian-suede shoe set on a flexible gum-rubber sole. Color(s): softy flint. Brand: To Boot New York. Style Name: To Boot New York 'Flanders' Double Monk Strap Shoe (Men). Style Number: 866363.
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Men's To Boot New York 'Glenn' Double Monk Strap Shoe

$395

Sleek style emanates from the full-grain leather finish of a handsome Italian monk shoe fitted with polished hardware. Color(s): alameda brown, pacific nero. Brand: To Boot New York. Style Name: To Boot New York 'Glenn' Double Monk Strap Shoe (Men). Style
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Men's To Boot New York 'Grant' Double Monk Shoe

On sale - now $296.25 - was $395

Exceptionally smooth leather defines a bold monk shoe cast in a clean silhouette. Color(s): alameda brown. Brand: To Boot New York. Style Name: To Boot New York 'Grant' Double Monk Shoe. Style Number: 722892.
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Men's To Boot New York 'Grant' Double Monk Shoe- Black

On sale - now $296.25 - was $395

Exceptionally smooth leather defines a bold monk shoe cast in a clean silhouette. Color(s): parma black. Brand: To Boot New York. Style Name: To Boot New York 'Grant' Double Monk Shoe. Style Number: 722892 1.
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Men's To Boot New York 'Harper' Driving Shoe

$295

Sleek lines and a clean sheen define a sharp driving shoe topped off with a smart penny keeper. Color(s): black, pragma t moro. Brand: To Boot New York. Style Name: To Boot New York 'Harper' Driving Shoe (Men). Style Number: 969687.
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Men's To Boot New York 'Harper' Driving Shoe, Brown

$295

Sleek lines and a clean sheen define a sharp driving shoe topped off with a smart penny keeper. Color(s): black, pragma t moro. Brand: To Boot New York. Style Name: To Boot New York 'Harper' Driving Shoe (Men). Style Number: 969687.
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Men's To Boot New York 'Hawthorne' Boot

$425

Cleanly styled ankle boot is fashioned with a round toe and easy side zip. Color(s): black leather, cognac leather, t moro. Brand: To Boot New York. Style Name: To Boot New York 'Hawthorne' Boot (Men). Style Number: 224239. Available In Stores.
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Men's To Boot New York 'Hawthorne' Boot, Black

$425

Cleanly styled ankle boot is fashioned with a round toe and easy side zip. Color(s): black leather, cognac leather, t moro. Brand: To Boot New York. Style Name: To Boot New York 'Hawthorne' Boot (Men). Style Number: 224239. Available In Stores.
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Men's To Boot New York 'Kyle' Driving Moccasin

$395

Soft, supple Italian leather upgrades a classic driving loafer shaped with a moc-stitched toe and braded lacing at the topline. Color(s): trapper cognac. Brand: To Boot New York. Style Name: To Boot New York 'Kyle' Driving Moccasin (Men). Style Number: 86
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Men's To Boot New York 'Layton' Chukka Boot Sneaker

$350

Buttery-soft Italian suede forms a laid-back chukka boot set on a sporty, sneaker-style sole. Color(s): softy flint/ cuoio. Brand: To Boot New York. Style Name: To Boot New York 'Layton' Chukka Boot Sneaker (Men). Style Number: 889799.
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Men's To Boot New York 'Marsden' Chukka Boot

$350

Crafted with a hearty welt, a sharp Italian chukka boot fashioned from soft suede features a comfy leather lining and a durable crepe rubber sole. Color(s): softy flint. Brand: To Boot New York. Style Name: To Boot New York 'Marsden' Chukka Boot (Men). St
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Men's To Boot New York 'Medford' Double Monk Strap Slip-On

On sale - now $296.25 - was $395

A burnished patina shapes a rich, earthy slip-on topped with a vintage-style double monk strap. Color(s): black, cognac. Brand: To Boot New York. Style Name: To Boot New York 'Medford' Double Monk Strap Slip-On. Style Number: 619352.
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Men's To Boot New York 'Milford' Plain Toe Buck Shoe

$350

Crafted with a hearty welt, a sharp Italian buck shoe fashioned from soft suede features a comfy leather lining and a durable crepe rubber sole. Color(s): softy blue. Brand: To Boot New York. Style Name: To Boot New York 'Milford' Plain Toe Buck Shoe (Men
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Men's To Boot New York 'Mitchell' Bit Driving Loafer

$325

Gleaming bit hardware stands out against the buttery-soft calfskin leather of a polished driving loafer crafted in Italy. Color(s): pragma nero. Brand: To Boot New York. Style Name: To Boot New York 'Mitchell' Bit Driving Loafer (Men). Style Number: 86624
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Men's To Boot New York 'Moore' Penny Loafer

$395

Rich, burnished leather shapes an apron-toe penny loafer accented with broguing above the stacked sole. Color(s): black, marrone. Brand: To Boot New York. Style Name: To Boot New York 'Moore' Penny Loafer (Men). Style Number: 743921.
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Men's To Boot New York 'Moore' Penny Loafer, Brown

On sale - now $296.25 - was $395

Rich, burnished leather shapes an apron-toe penny loafer accented with broguing above the stacked sole. Color(s): brown. Brand: To Boot New York. Style Name: To Boot New York 'Moore' Penny Loafer (Men). Style Number: 743921 2.
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Men's To Boot New York 'Moore' Penny Loafer- Black

$395

Rich, burnished leather shapes an apron-toe penny loafer accented with broguing above the stacked sole. Color(s): black, marrone. Brand: To Boot New York. Style Name: To Boot New York 'Moore' Penny Loafer (Men). Style Number: 743921.
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Men's To Boot New York 'Senato' Penny Loafer

On sale - now $243.75 - was $325

Semigloss leather shapes an Italian-crafted penny loafer set on a stacked sole. The upper will soften at flex points with minimal wear, giving the shoe a more relaxed appeal. Color(s): black, brown. Brand: To Boot New York. Style Name: To Boot New York 'S
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Men's To Boot New York 'Senato' Penny Loafer, Black

On sale - now $243.75 - was $325

Semigloss leather shapes an Italian-crafted penny loafer set on a stacked sole. The upper will soften at flex points with minimal wear, giving the shoe a more relaxed appeal. Color(s): black, brown. Brand: To Boot New York. Style Name: To Boot New York 'S
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Men's To Boot New York 'Spencer' Longwing Oxford

$350

Sharp brogue details shape a classic longwing shaped from soft suede and set on a crepe rubber sole. Color(s): pernice brown. Brand: To Boot New York. Style Name: To Boot New York 'Spencer' Longwing Oxford. Style Number: 617047.
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Men's To Boot New York 'Spencer' Longwing Oxford- Brown

$350

Sharp brogue details shape a classic longwing shaped from soft suede and set on a crepe rubber sole. Color(s): pernice brown. Brand: To Boot New York. Style Name: To Boot New York 'Spencer' Longwing Oxford. Style Number: 617047.
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Men's To Boot New York 'Stallworth' Cap Toe Boot

On sale - now $337.5 - was $450

Hearty coloring and a distinctive shine ensure a glowing warmth in a bold, vintage-inspired boot cast in a sleek silhouette to complete the bolder look. Color(s): black, cognac. Brand: To Boot New York. Style Name: To Boot New York 'Stallworth' Cap Toe Bo
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Men's To Boot New York 'Stallworth' Cap Toe Boot, Black

On sale - now $337.5 - was $450

Hearty coloring and a distinctive shine ensure a glowing warmth in a bold, vintage-inspired boot cast in a sleek silhouette to complete the bolder look. Color(s): black, cognac. Brand: To Boot New York. Style Name: To Boot New York 'Stallworth' Cap Toe Bo
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Men's To Boot New York 'Stark' Cap Toe Derby

On sale - now $199.9 - was $325

A medallion-stamped toe box marks a harp derby crafted from lustrous leather for a tasteful shine. Color(s): vitello black, vitello cuoio brown. Brand: To Boot New York. Style Name: To Boot New York 'Stark' Cap Toe Derby (Men). Style Number: 835161.
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Men's To Boot New York 'Warwick' Cap Toe Oxford

$450

A gleaming burnished toe caps off a sophisticated sartorial oxford. Color(s): black, tan 399. Brand: To Boot New York. Style Name: To Boot New York 'Warwick' Cap Toe Oxford. Style Number: 355177.
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Men's To Boot New York 'Weldon' Leather Cap Toe Oxford

$450

Handsome broguing puts a distinctive stamp on a rich oxford fashioned from high-caliber calfskin leather. Color(s): parmadoc grey, tan. Brand: To Boot New York. Style Name: To Boot New York 'Weldon' Leather Cap Toe Oxford (Men). Style Number: 743957.
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Men's To Boot New York 'Winston' Oxford

$395

Smooth leather accentuates the sleek cut of a plain-toe oxford set on a stacked sole. Color(s): berry black, berry tan. Brand: To Boot New York. Style Name: To Boot New York 'Winston' Oxford. Style Number: 393735.
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Men's To Boot New York 'Winston' Oxford, Black

$395

Smooth leather accentuates the sleek cut of a plain-toe oxford set on a stacked sole. Color(s): berry black, berry tan. Brand: To Boot New York. Style Name: To Boot New York 'Winston' Oxford. Style Number: 393735.
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Men's To Boot New York Cap Toe Oxford

$395

Exceptional broguing marks a handsome cap-toe oxford shaped from richly burnished leather. Color(s): brown, parma black. Brand: To Boot New York. Style Name: To Boot New York Cap Toe Oxford. Style Number: 725832.
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Men's To Boot New York Cap Toe Oxford, Brown

$395

Exceptional broguing marks a handsome cap-toe oxford shaped from richly burnished leather. Color(s): brown, parma black. Brand: To Boot New York. Style Name: To Boot New York Cap Toe Oxford. Style Number: 725832.
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To Boot New York - Aruba (Black Trapper) Men's Shoes

$265

Slip into luxurious style with the To Boot New York Aruba. Leather upper with woven details. Slip-on construction. Open toe slide sandal silhouette. Leather lining and insole. Synthetic outsole. Made in Italy. Measurements:Weight: 10 ozProduct measurement
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To Boot New York - Ashton (Aubergine Softy) Men's Shoes

$295

Slip into a dreamy comfort with this moc driver loafer by To Boot New York! Suede upper. Slip-on construction. Loafer with penny keeper detail. Contrast stitched detail with a moc toe. Leather lining and insole. Leather/textile outsole. Made in Italy and
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To Boot New York - Ashton (Black/Be Softy) Men's Shoes

$295

Slip into a dreamy comfort with this moc driver loafer by To Boot New York! Suede upper. Slip-on construction. Loafer with penny keeper detail. Contrast stitched detail with a moc toe. Leather lining and insole. Leather/textile outsole. Made in Italy and
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To Boot New York - Ashton (Brown/Be Softy) Men's Shoes

$295

Slip into a dreamy comfort with this moc driver loafer by To Boot New York! Suede upper. Slip-on construction. Loafer with penny keeper detail. Contrast stitched detail with a moc toe. Leather lining and insole. Leather/textile outsole. Made in Italy and
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To Boot New York - Barbados (Black Trapper) Men's Shoes

$275

Dress up your day with the charming style of the To Boot New York Barbados. Leather upper with tonal stitching. Adjustable cross foot strap with hook and loop closure. Closed toe silhouette. Leather lining. Lightly cushioned man-made insole. Man-made outs
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To Boot New York - Barbados (Cognac Trapper) Men's Shoes

$275

Dress up your day with the charming style of the To Boot New York Barbados. Leather upper with tonal stitching. Adjustable cross foot strap with hook and loop closure. Closed toe silhouette. Leather lining. Lightly cushioned man-made insole. Man-made outs
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To Boot New York - Brennan (Trapper Black) Men's Shoes

$450

Bring a touch of refinement to your casual wardrobe with the Brennan boot. Burnished leather upper. Lace-up closure. Wing tip design with brogue detailing. Leather lining. Man-made sole. Made in Italy. Please note that typically these boots run 1/2 size l
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To Boot New York - Brennan (Trapper Cognac 8660) Men's Shoes

$450

Bring a touch of refinement to your casual wardrobe with the Brennan boot. Burnished leather upper. Lace-up closure. Wing tip design with brogue detailing. Leather lining. Man-made sole. Made in Italy. Please note that typically these boots run 1/2 size l
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To Boot New York - Brennan (Trapper Tmoro) Men's Shoes

$450

Bring a touch of refinement to your casual wardrobe with the Brennan boot. Burnished leather upper. Lace-up closure. Wing tip design with brogue detailing. Leather lining. Man-made sole. Made in Italy. Please note that typically these boots run 1/2 size l
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To Boot New York - Brighton (Tan Berry) Men's Shoes

$395

Create a classic look with a contemporary twist in these To Boot New York shoes. Leather upper with tonal stitching. Monk strap with dual buckle closures. Stitched cap toe detail. Ankle boot silhouette. Leather lining and insole. Genuine leather outsole.
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To Boot New York - Burns (Tan) Men's Shoes

$450

Make yourself stand out from the crowd in the To Boot New York Burns. Leather upper with tonal stitching. Monk strap with dual buckle closures. Perforated brogue details. Leather lining and insole. Durable leather outsole. Made in Italy. Measurements:Heel
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To Boot New York - Burton (Black/Black) Men's Shoes

$450

Refine your style with the timeless designs of To Boot New York. Dual panel leather upper. Tonal stitching with perforated brogue details. Lace up front closure with blind eyelets. Leather lining and insole. Genuine leather outsole. Made in Italy. Measure
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To Boot New York - Campbell (Black Parma) Men's Shoes

$395

Refine your look with these exceptional loafers. Leather upper. Adjustable monk-strap closure. Leather lining and insole. Stacked heel. Leather sole. Made in Italy. Measurements:Heel Height: 1 inWeight: 1 lb 1 ozProduct measurements were taken using size
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To Boot New York - Capote (Black Parma) Men's Lace Up Cap Toe Shoes

$395

Please note, this style runs large. To Boot New York suggests you order a size smaller than your normal size. For example, if you normally wear a size 10, order a size 9. Inject sophistication into your ensemble with these dashing oxfords. Leather upper.
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To Boot New York - Capote (Tek Spec Parma) Men's Lace Up Cap Toe Shoes

$395

Please note, this style runs large. To Boot New York suggests you order a size smaller than your normal size. For example, if you normally wear a size 10, order a size 9. Inject sophistication into your ensemble with these dashing oxfords. Leather upper.
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To Boot New York - Carter (Black) Men's Shoes

$395

Rule the office in the stately To Boot New York Carter. Smooth leather upper with tonal stitching. Lace up front closure with blind eyelets. Stitched toe. Leather lining and insole. Durable leather outsole. Made in Italy. Measurements:Heel Height: 1 1 4 i
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To Boot New York - Carter (Brown) Men's Shoes

$395

Rule the office in the stately To Boot New York Carter. Smooth leather upper with tonal stitching. Lace up front closure with blind eyelets. Stitched toe. Leather lining and insole. Durable leather outsole. Made in Italy. Measurements:Heel Height: 1 1 4 i
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To Boot New York - Carter (Cognac) Men's Shoes

$395

Rule the office in the stately To Boot New York Carter. Smooth leather upper with tonal stitching. Lace up front closure with blind eyelets. Stitched toe. Leather lining and insole. Durable leather outsole. Made in Italy. Measurements:Heel Height: 1 1 4 i
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To Boot New York - Clarkston (Sigaro 336) Men's Lace up casual Shoes

$350

Perfect your casual look with these impeccable chukka boots! Suede upper. Lace-up front. Stitch detailing. Leather lining and insole. Synthetic sole. Made in Italy. Measurements:Heel Height: 1 inWeight: 1 lb 6 ozProduct measurements were taken using size
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To Boot New York - Cornell (Trapper Cognac) Men's Shoes

$398

Refine your style with the timeless designs of To boot New York. Burnished leather upper with tonal stitching. Lace up front closure with blind eyelets. Chukka boot silhouette. Leather lining and insole. Durable synthetic outsole. Made in Italy. Measureme
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To Boot New York - Corporal (Tan/Camouflage) Men's Shoes

$350

Refine your style with the timeless designs of To Boot New York. Dual panel leather upper with tonal stitching. Perforated brogue details. Lace up front closure with metal eyelets. Wingtip oxford silhouette. Leather lining and insole. Lugged rubber outsol
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To Boot New York - Dale (Blue Softy) Men's Shoes

$350

Take your style to new levels with the extraordinary designs of To Boot New York. Leather upper with tonal stitching. Lace up front closure with metal eyelets. Leather lining and insole. Durable rubber outsole. Made in Italy. Measurements:Weight: 1 lb 5 o
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To Boot New York - Darrell (Dark Brown) Men's Shoes

$398

Refine your style with the timeless designs of To boot New York. Burnished leather upper with tonal stitching. Lace up front closure with blind eyelets. Perforated brogue details. Leather lining and insole. Durable synthetic outsole. Made in Italy. Measur
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To Boot New York - Denton (Black Plonge/Black Softy) Men's Shoes

$350

Lace into leisurely style in the comfortable cool of the To Boot New York Denton. Leather and suede upper with tonal stitching. Lace up front closure with metal eyelets. Leather lining and insole. Flexible synthetic outsole. Made in Italy. Measurements:We
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To Boot New York - Drummond (Cognac Roma) Men's Shoes

$398

Create a sleek look with the To Boot New York Drummond. Leather upper with tonal stitching. Pull tab at heel. Pull-on construction with elastic side goring for on-and-off ease. Chelsea boot silhouette. Leather lining and insole. Durable synthetic outsole.
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To Boot New York - Duke (Black) Men's Shoes

$450

Define your style with the sleek and elegant To Boot New York Duke. Leather upper with tonal stitching. Lace up oxford front with blind eyelets. Perforated brogue details. Leather lining and insole. Genuine leather outsole. Made in Italy. Measurements:Hee
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To Boot New York - Duke (Cognac) Men's Shoes

$450

Define your style with the sleek and elegant To Boot New York Duke. Leather upper with tonal stitching. Lace up oxford front with blind eyelets. Perforated brogue details. Leather lining and insole. Genuine leather outsole. Made in Italy. Measurements:Hee
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To Boot New York - Enrico (Black) Men's Shoes

$450

Refine your style with the timeless designs of To Boot New York. Smooth leather upper with tonal stitching. Lace up front closure with blind eyelets. Perforated toe accent. Leather lining and insole. Genuine leather outsole. Made in Italy. Measurements:He
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To Boot New York - Enrico (Cognac) Men's Shoes

$450

Refine your style with the timeless designs of To Boot New York. Smooth leather upper with tonal stitching. Lace up front closure with blind eyelets. Perforated toe accent. Leather lining and insole. Genuine leather outsole. Made in Italy. Measurements:He
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To Boot New York - Farley (Bianco Plonge) Men's Shoes

$350

Dress up your day with the charming style of the To Boot New York Farley. Leather upper with tonal stitching. Lace up front closure with metal eyelets. Leather lining and insole. Durable synthetic outsole. Made in Italy. Measurements:Weight: 1 lb 3 ozProd
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To Boot New York - Farley (Black Plonge) Men's Shoes

$350

Dress up your day with the charming style of the To Boot New York Farley. Leather upper with tonal stitching. Lace up front closure with metal eyelets. Leather lining and insole. Durable synthetic outsole. Made in Italy. Measurements:Weight: 1 lb 3 ozProd
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To Boot New York - Felix (Black Leather) Men's Shoes

$325

Please note, this style runs large. To Boot New York suggests you order a half size smaller than your normal size. For example, if you normally wear a size 10, order a size 9. 5Pursue perfection in the polished refinement of the To Boot New York Felix. Le
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To Boot New York - Felix (Brown Leather) Men's Shoes

$325

Please note, this style runs large. To Boot New York suggests you order a half size smaller than your normal size. For example, if you normally wear a size 10, order a size 9. 5Pursue perfection in the polished refinement of the To Boot New York Felix. Le
more...

To Boot New York - Filbert (Tan Roma) Men's Shoes

$350

Dress up your day with the charming style of the To Boot New York Filbert. Leather upper with tonal stitching. Monk strap with dual buckle closures. Leather lining and insole. Crepe rubber outsole. Made in Italy. Measurements:Heel Height: 1 inWeight: 1 lb
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To Boot New York - Flanders (Flirt Softy) Men's Shoes

$350

Create a classic look with a contemporary twist in these To Boot New York shoes. Suede leather upper with tonal stitching. Monk strap with dual buckle closures. Stitched cap toe detail. Leather lining and insole. Crepe rubber outsole. Made in Italy. Measu
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To Boot New York - Gallis (Cognac Canyon) Men's Shoes

$450

Tap into your rugged side with the rough and rebellious appeal of the To Boot New York Gallis. Leather upper with tonal stitching. Monk strap with two buckle closures. Inside zip closure. Leather lining and insole. Durable synthetic outsole. Made in Italy
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To Boot New York - Gallis (Sigaro Softy) Men's Shoes

$450

Tap into your rugged side with the rough and rebellious appeal of the To Boot New York Gallis. Leather upper with tonal stitching. Monk strap with two buckle closures. Inside zip closure. Leather lining and insole. Durable synthetic outsole. Made in Italy
more...

To Boot New York - Geoffrey (Cigaro/Cuoio Softy) Men's Shoes

$350

Take your style to new levels with the extraordinary designs of To Boot New York. Leather upper with tonal stitching. Lace up front closure with metal eyelets. Leather lining and insole. Durable rubber outsole. Made in Italy. Measurements:Weight: 1 lb 3 o
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To Boot New York - Geoffrey (Flint Softy) Men's Shoes

$350

Take your style to new levels with the extraordinary designs of To Boot New York. Leather upper with tonal stitching. Lace up front closure with metal eyelets. Leather lining and insole. Durable rubber outsole. Made in Italy. Measurements:Weight: 1 lb 3 o
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To Boot New York - Geoffrey (Indaco Otter) Men's Shoes

$350

Take your style to new levels with the extraordinary designs of To Boot New York. Leather upper with tonal stitching. Lace up front closure with metal eyelets. Leather lining and insole. Durable rubber outsole. Made in Italy. Measurements:Weight: 1 lb 3 o
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To Boot New York - Giovanni (Blue Softy) Men's Shoes

$350

Take your style to new levels with the extraordinary designs of To Boot New York. Leather upper with tonal stitching. Slip-on construction. Leather lining and insole. Flexible rubber outsole. Made in Italy. Measurements:Weight: 1 lb 3 ozProduct measuremen
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To Boot New York - Giovanni (Flint Softy) Men's Shoes

$350

Take your style to new levels with the extraordinary designs of To Boot New York. Leather upper with tonal stitching. Slip-on construction. Leather lining and insole. Flexible rubber outsole. Made in Italy. Measurements:Weight: 1 lb 3 ozProduct measuremen
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To Boot New York - Glenn (Black Pacific) Men's Shoes

$395

Dial in supreme executive style with the To Boot New York Glenn. Smooth leather upper with tonal stitching. Monk strap with dual buckle closures. Plain toe monk strap oxford silhouette. Leather lining and insole. Synthetic and leather outsole. Made in Ita
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To Boot New York - Glenn (Brown Alameda) Men's Shoes

$395

Dial in supreme executive style with the To Boot New York Glenn. Smooth leather upper with tonal stitching. Monk strap with dual buckle closures. Plain toe monk strap oxford silhouette. Leather lining and insole. Synthetic and leather outsole. Made in Ita
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To Boot New York - Glyndon (Cognac Praga) Men's Shoes

$375

Create a finished and refined look in the effortless style of To Boot New York. Leather upper with tonal stitching. Lace up front closure with metal eyelets. Wingtip detail at toe. Leather lining and insole. Durable synthetic outsole. Made in Italy. Measu
more...

To Boot New York - Greene (Black) Men's Shoes

$350

Refine your style with the timeless designs of To Boot New York. Textured leather upper with tonal stitching. Slip-on loafer construction. Leather vamp strap with penny keeper detail. Stitched moc toe. Leather lining and insole. Durable synthetic outsole.
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To Boot New York - Guilford (Cognac Canyon) Men's Shoes

$398

Make a lasting mark on the world with the impressive design of the To Boot New York Guilford. Leather upper with burnished accents. Lace up front closure with blind eyelets. Burnished toe detail. Leather lining and insole. Durable synthetic outsole. Made
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To Boot New York - Guilford (Ebano Canyon) Men's Shoes

$398

Make a lasting mark on the world with the impressive design of the To Boot New York Guilford. Leather upper with burnished accents. Lace up front closure with blind eyelets. Burnished toe detail. Leather lining and insole. Durable synthetic outsole. Made
more...

To Boot New York - Hammel (Cognac Trapper) Men's Shoes

$395

Create a classic look with a contemporary twist in these To Boot New York shoes. Suede leather upper with tonal stitching. Slip-on loafer construction. Leather vamp strap with penny keeper detail. Stitched toe detail. Leather lining and insole. Durable sy
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To Boot New York - Hammel (Sigaro Softy) Men's Shoes

$395

Create a classic look with a contemporary twist in these To Boot New York shoes. Suede leather upper with tonal stitching. Slip-on loafer construction. Leather vamp strap with penny keeper detail. Stitched toe detail. Leather lining and insole. Durable sy
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To Boot New York - Harper (Black) Men's Shoes

$295

Treat your feet to luxury with these plush To Boot New York Harper penny loafers. Rich leather upper. Stitched details. Leather strap at vamp with classic penny keeper detail. Moc toe. Leather lining and insole. Man-made outsole. Made in Italy. Measuremen
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To Boot New York - Harper (Brown) Men's Shoes

$295

Treat your feet to luxury with these plush To Boot New York Harper penny loafers. Rich leather upper. Stitched details. Leather strap at vamp with classic penny keeper detail. Moc toe. Leather lining and insole. Man-made outsole. Made in Italy. Measuremen
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To Boot New York - Harper (Tmoro Praga) Men's Shoes

$295

Treat your feet to luxury with these plush To Boot New York Harper penny loafers. Rich leather upper. Stitched details. Leather strap at vamp with classic penny keeper detail. Moc toe. Leather lining and insole. Man-made outsole. Made in Italy. Measuremen
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To Boot New York - Hillis (Black Parmadoc) Men's Shoes

$485

Create a finished and refined look in the effortless style of To Boot New York. Leather upper with tonal stitching. Pull loop at shaft opening. Pull-on construction with elastic side goring for on-and-off ease. Chelsea boot silhouette. Leather lining and
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To Boot New York - Hillis (Grey Parmadoc) Men's Shoes

$485

Create a finished and refined look in the effortless style of To Boot New York. Leather upper with tonal stitching. Pull loop at shaft opening. Pull-on construction with elastic side goring for on-and-off ease. Chelsea boot silhouette. Leather lining and
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To Boot New York - Hillis (Tan Parmadoc) Men's Shoes

$485

Create a finished and refined look in the effortless style of To Boot New York. Leather upper with tonal stitching. Pull loop at shaft opening. Pull-on construction with elastic side goring for on-and-off ease. Chelsea boot silhouette. Leather lining and
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To Boot New York - Keegan (Black Parmadoc) Men's Shoes

$495

Channel rugged style with the handsome To Boot New York Keegan. Smooth leather upper with tonal stitching. Inside zip closure. Plain toe ankle boot silhouette. Leather lining and insole. Genuine leather outsole. Made in Italy. Measurements:Heel Height: 1
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To Boot New York - Layton (Blue/Blue Softy) Men's Shoes

$350

Take your style to new levels with the extraordinary designs of To Boot New York. Leather upper with tonal stitching. Lace up front closure with metal eyelets. Chukka boot inspired design. Leather lining and insole. Durable rubber outsole. Made in Italy.
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To Boot New York - Layton (Flint/Cuoio Softy) Men's Shoes

$350

Take your style to new levels with the extraordinary designs of To Boot New York. Leather upper with tonal stitching. Lace up front closure with metal eyelets. Chukka boot inspired design. Leather lining and insole. Durable rubber outsole. Made in Italy.
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To Boot New York - Linden (Flint Softy) Men's Shoes

$295

The To Boot New York Linden is the perfect choice for a day spent out on the town or a night in with good company. Leather upper with tonal stitching. Slip-on loafer construction. Leather vamp strap with penny keeper detail. Stitched moc toe. Leather lini
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To Boot New York - Marsden (Flint Softy) Men's Shoes

$350

Create a finished and refined look in the effortless style of To Boot New York. Suede leather upper with tonal stitching. Lace up front closure with blind eyelets. Chukka boot silhouette. Plain toe. Leather lining and insole. Crepe rubber outsole. Made in
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To Boot New York - Miguel (Black Vacchetta) Men's Shoes

$175

Create a finished and refined look in the effortless style of To Boot New York. Leather upper with woven construction. Slide-on sandal design. Leather lining and insole. Durable man-made outsole. Made in Italy. Measurements:Weight: 11 ozProduct measuremen
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To Boot New York - Miguel (Marrone Vacchetta) Men's Shoes

$175

Create a finished and refined look in the effortless style of To Boot New York. Leather upper with woven construction. Slide-on sandal design. Leather lining and insole. Durable man-made outsole. Made in Italy. Measurements:Weight: 11 ozProduct measuremen
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To Boot New York - Milford (Blue Softy) Men's Shoes

$350

Create a classic look with a contemporary twist in these To Boot New York shoes. Leather upper with tonal stitching. Lace up front closure with blind eyelets. Plain toe oxford silhouette. Leather lining and insole. Crepe rubber outsole. Made in Italy. Mea
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To Boot New York - Moore (Brown) Men's Shoes

$395

Stay classy in the refined looks of the To Boot New York Moore. Smooth leather upper with tonal stitching. Slip-on loafer construction. Leather vamp strap with penny keeper detail. Stitched toe accent. Leather lining and insole. Genuine leather outsole. M
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To Boot New York - Moore (Cognac) Men's Shoes

$395

Stay classy in the refined looks of the To Boot New York Moore. Smooth leather upper with tonal stitching. Slip-on loafer construction. Leather vamp strap with penny keeper detail. Stitched toe accent. Leather lining and insole. Genuine leather outsole. M
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To Boot New York - Nicholsen (Black) Men's Shoes

$450

Refine your style with the timeless designs of To Boot New York. Smooth, burnished leather upper with tonal stitching. Slip-on loafer construction. Leather vamp straps. Stitched toe detail. Leather lining and insole. Genuine leather outsole with rubber he
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To Boot New York - Nicholsen (Tan) Men's Shoes

$450

Refine your style with the timeless designs of To Boot New York. Smooth, burnished leather upper with tonal stitching. Slip-on loafer construction. Leather vamp straps. Stitched toe detail. Leather lining and insole. Genuine leather outsole with rubber he
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To Boot New York - Panama (Black Vacchetta) Men's Shoes

$195

Dress up your day with the charming style of the To Boot New York Panama. Leather upper with tonal stitching. Adjustable ankle strap with buckle closure. Closed toe silhouette. Man-made lining and insole. Man-made outsole. Made in Italy. Measurements:Heel
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To Boot New York - Panama (Quercia Vacchetta) Men's Shoes

$195

Dress up your day with the charming style of the To Boot New York Panama. Leather upper with tonal stitching. Adjustable ankle strap with buckle closure. Closed toe silhouette. Man-made lining and insole. Man-made outsole. Made in Italy. Measurements:Heel
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To Boot New York - Parrish (Tmoro Praga) Men's Shoes

$395

Create a finished and refined look in the effortless style of To Boot New York. Smooth leather upper with tonal stitching. Lace up front closure with metal eyelets. Chukka boot silhouette. Leather lining and insole. Synthetic outsole. Made in Italy. Measu
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To Boot New York - Penn (Brown) Men's Shoes

$350

Refine your style with the timeless designs of To Boot New York. Leather upper with tonal stitching. Lace up front closure with blind eyelets. Plain toe oxford silhouette. Leather lining and insole. Durable synthetic outsole. Made in Italy. Measurements:H
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To Boot New York - Penn (Grey) Men's Shoes

$350

Refine your style with the timeless designs of To Boot New York. Leather upper with tonal stitching. Lace up front closure with blind eyelets. Plain toe oxford silhouette. Leather lining and insole. Durable synthetic outsole. Made in Italy. Measurements:H
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To Boot New York - Richards (Tan Berry) Men's Shoes

$395

Create a finished and refined look in the effortless style of To Boot New York. Leather upper with tonal stitching. Monk strap with single buckle closure. Perforated brogue details. Leather lining and insole. Genuine leather outsole. Made in Italy. Measur
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To Boot New York - Richards (Tmoro Berry) Men's Shoes

$395

Create a finished and refined look in the effortless style of To Boot New York. Leather upper with tonal stitching. Monk strap with single buckle closure. Perforated brogue details. Leather lining and insole. Genuine leather outsole. Made in Italy. Measur
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To Boot New York - Richter (Cognac Praga) Men's Shoes

$375

Create a finished and refined look in the effortless style of To Boot New York. Smooth leather upper with tonal stitching. Lace up front closure with metal eyelets. Plain toe oxford silhouette. Leather lining and insole. Durable synthetic outsole. Made in
more...

To Boot New York - Richter (Tmoro Praga) Men's Shoes

$375

Create a finished and refined look in the effortless style of To Boot New York. Smooth leather upper with tonal stitching. Lace up front closure with metal eyelets. Plain toe oxford silhouette. Leather lining and insole. Durable synthetic outsole. Made in
more...

To Boot New York - Riggins (Trapper Black) Men's Shoes

$450

Refine your style with the timeless designs of To Boot New York. Smooth leather upper with tonal stitching and perforated details. Pull loop at collar. Pull-on construction with elastic side goring for on-and-off ease. Perforated toe accent. Leather linin
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To Boot New York - Robinson (Blue Softy) Men's Shoes

$375

Create a finished and refined look in the effortless style of To Boot New York. Suede leather upper with tonal stitching. Lace up front closure with metal eyelets. Chukka boot silhouette. Plain toe. Leather lining and insole. Durable synthetic outsole. Ma
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To Boot New York - Scott (Trapper Black) Men's Shoes

$475

Refine your style with the timeless designs of To Boot New York. Smooth leather upper with tonal stitching. Inside zip closure. Plain toe ankle boot silhouette. Leather lining and insole. Durable leather and synthetic outsole. Made in Italy. Measurements:
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To Boot New York - Sheppard (Flint Softy) Men's Shoes

$375

Create a finished and refined look in the effortless style of To Boot New York. Suede leather and synthetic upper with tonal stitching. Pull loop at shaft opening. Contrast elastic goring at sides for on-and-off ease. Pull-on Chelsea boot construction. Le
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To Boot New York - Sheridan (Black Trapper) Men's Shoes

$398

Create a finished and refined look in the effortless style of To Boot New York. Leather upper with tonal stitching. Padded collar. Lace up front closure with blind eyelets. Leather lining and insole. Synthetic sawtooth outsole. Made in Italy. Measurements
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To Boot New York - Sheridan (Cognac Trapper) Men's Shoes

$398

Create a finished and refined look in the effortless style of To Boot New York. Leather upper with tonal stitching. Padded collar. Lace up front closure with blind eyelets. Leather lining and insole. Synthetic sawtooth outsole. Made in Italy. Measurements
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To Boot New York - Sheridan (Navy Trapper) Men's Shoes

$398

Create a finished and refined look in the effortless style of To Boot New York. Leather upper with tonal stitching. Padded collar. Lace up front closure with blind eyelets. Leather lining and insole. Synthetic sawtooth outsole. Made in Italy. Measurements
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To Boot New York - Stallworth (Trapper Cognac) Men's Shoes

$450

Dress up or down in the refined Stallworth boot. Leather upper. Lace-up closure. Cap toe. Leather lining. Imported. Please note that these boots typically run 1/2 size larger. It is suggested to order your size accordingly. Measurements:Heel Height: 1 1 4
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To Boot New York - Tanner (Bianco Bott) Men's Shoes

$325

Kick back in luxe leisurely style with the To Boot New York Tanner. Leather upper with tonal stitching. Slip-on loafer construction. Metallic vamp hardware. Stitched moc toe. Leather lining and insole. Durable synthetic outsole. Made in Italy. Measurement
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To Boot New York - Tristan (Cuoio Parmadoc) Men's Shoes

$450

Create a classic look with a contemporary twist in these To Boot New York shoes. Leather upper with tonal stitching. Monk strap with buckle closure. Perforated toe detail. Leather lining and insole. Genuine leather outsole. Made in Italy. Measurements:Hee
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To Boot New York - Warwick (Parma Tan) Men's Lace Up Cap Toe Shoes

$450

Bring dapper back with these burnished beauties! Leather upper with pinked trim. Lace-up front. Perforated and stitched detailing. Cap toe. Leather lining and insole. Leather sole. Made in Italy. Measurements:Heel Height: 1 1 4 inWeight: 1 lbPlatform Heig
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To Boot New York - Weldon (Bordo) Men's Shoes

$450

Dress sharper than a razor in the To Boot New York Weldon. Smooth leather upper with tonal stitching. Lace up front closure with blind eyelets. Perforated details. Cap toe derby oxford silhouette. Leather lining and insole. Genuine leather outsole. Made i
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To Boot New York - Wesley (Black Trapper) Men's Shoes

$450

Dress up your day with the charming style of the To Boot New York Wesley. Leather and fabric upper with tonal stitching. Pull-on Chelsea boot silhouette. Pull loop at shaft opening. Leather and textile lining. Man-made insole. Man-made outsole. Made in It
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To Boot New York - Wesley (Cognac Trapper) Men's Shoes

$450

Dress up your day with the charming style of the To Boot New York Wesley. Leather and fabric upper with tonal stitching. Pull-on Chelsea boot silhouette. Pull loop at shaft opening. Leather and textile lining. Man-made insole. Man-made outsole. Made in It
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To Boot New York Albert (Bronx Light Ebano 595) Men's Shoes

On sale - now $275 - was $498

This suede boot has a great rugged appeal for those who want to express their masculine attitude. Oiled suede upper. Duel side-zip closures. Strap with metal buckle detail. Round toe with block heel. Leather lining and insole. Man-made outsole. Imported.
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To Boot New York Altman (Black) Men's Shoes

On sale - now $179.99 - was $299

Refine your style with the timeless designs of To boot New York. Smooth leather upper with tonal stitching. Cross foot straps with hook and loop closure. Leather lining and insole. Textured synthetic outsole. Made in Italy. Measurements:Heel Height: 3 4 i
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To Boot New York Altman (Cognac) Men's Shoes

On sale - now $179.99 - was $299

Refine your style with the timeless designs of To boot New York. Smooth leather upper with tonal stitching. Cross foot straps with hook and loop closure. Leather lining and insole. Textured synthetic outsole. Made in Italy. Measurements:Heel Height: 3 4 i
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To Boot New York Antonio (Camouflage) Men's Lace-up Boots

On sale - now $209.99 - was $350

Refine your style with the timeless designs of To Boot New York. Suede leather upper with tonal stitching. Lace up front closure with metal eyelets. Chukka boot silhouette. Leather lining and insole. Lugged synthetic outsole. Made in Italy. Measurements:H
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To Boot New York Ashton (Blue/Be Otter B) Men's Shoes

On sale - now $161.99 - was $295

Slip into a dreamy comfort with this moc driver loafer by To Boot New York! Suede upper. Slip-on construction. Loafer with penny keeper detail. Contrast stitched detail with a moc toe. Leather lining and insole. Leather/textile outsole. Made in Italy and
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To Boot New York Ashton (Grey/Be Otter) Men's Shoes

On sale - now $161.99 - was $295

Slip into a dreamy comfort with this moc driver loafer by To Boot New York! Suede upper. Slip-on construction. Loafer with penny keeper detail. Contrast stitched detail with a moc toe. Leather lining and insole. Leather/textile outsole. Made in Italy and
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To Boot New York Bloor (Softy Blue) Men's Shoes

On sale - now $119.99 - was $295

Cheers to comfort with a casual and trendy appeal with the Bloor. Suede upper. Slip-on loafer. Stitched detailing. Moc toe. Shearling lining. Synthetic insole. Man-made outsole. Imported. Measurements:Heel Height: 1 2 inWeight: 14 ozProduct measurements w
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To Boot New York Bloor (Softy Pepe) Men's Shoes

On sale - now $119.99 - was $295

Cheers to comfort with a casual and trendy appeal with the Bloor. Suede upper. Slip-on loafer. Stitched detailing. Moc toe. Shearling lining. Synthetic insole. Man-made outsole. Imported. Measurements:Heel Height: 1 2 inWeight: 14 ozProduct measurements w
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To Boot New York Carl (Dark Brown) Men's Shoes

On sale - now $209.99 - was $350

Refine your style with the timeless designs of To Boot New York. Suede upper with contrast and tonal stitching. Slip-on loafer construction. Stitched moc toe. Leather lining and insole. Crepe rubber outsole. Made in Italy. Measurements:Heel Height: 1 inWe
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To Boot New York Carl (Softy Black) Men's Shoes

On sale - now $209.99 - was $350

Refine your style with the timeless designs of To Boot New York. Suede upper with contrast and tonal stitching. Slip-on loafer construction. Stitched moc toe. Leather lining and insole. Crepe rubber outsole. Made in Italy. Measurements:Heel Height: 1 inWe
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To Boot New York Cruz (Trapper Black) Men's Shoes

On sale - now $344.99 - was $575

Refine your style with the timeless designs of To boot New York. Smooth leather upper with tonal stitching. Adjustable ankle strap with buckle closure. Ankle boot silhouette. Inside zip closure. Leather lining and insole. Durable leather and rubber outsol
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To Boot New York Darrin (Militare Vachetta) Men's Shoes

On sale - now $191.99 - was $350

The crepe rubber sole and elegant brogue details of the Darrin oxford will get you noticed for all of the right reasons. Rich leather upper. Lace-up front with blind eyelets. Brogue detailing. Leather lining and insole. Rubber crepe sole. Made in Italy. M
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To Boot New York Duke (Bordo) Men's Shoes

On sale - now $246.99 - was $450

Define your style with the sleek and elegant To Boot New York Duke. Leather upper with tonal stitching. Lace up oxford front with blind eyelets. Perforated brogue details. Leather lining and insole. Genuine leather outsole. Made in Italy. Measurements:Hee
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To Boot New York Erikson (Oceano Nabuk Piuma) Men's Shoes

On sale - now $151.99 - was $335

The Erikson is a smart looking loafer with a stellar design! Suede upper. Slip-on. Stitched detailing with a moc toe. Leather lining and insole. Man-made outsole. Made in Italy and imported. Measurements:Heel Height: 1 inWeight: 1 lb 4 ozProduct measureme
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To Boot New York Felix (Black Suede) Men's Shoes

On sale - now $179.99 - was $325

Please note, this style runs large. To Boot New York suggests you order a half size smaller than your normal size. For example, if you normally wear a size 10, order a size 9. 5Pursue perfection in the polished refinement of the To Boot New York Felix. Le
more...

To Boot New York Greyson (Brown) Men's Shoes

On sale - now $269.99 - was $450

Refine your style with the timeless designs of To Boot New York. Burnished leather upper with tonal stitching. Inside zip closure. Burnished toe accent. Leather lining and insole. Durable leather and synthetic outsole. Made in Italy. Measurements:Heel Hei
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To Boot New York Hanes (Trapper Black) Men's Shoes

On sale - now $329.99 - was $550

Refine your style with the timeless designs of To Boot New York. Smooth calfskin upper with tonal stitching. Padded collar with pull tab. Lace up front closure with blind eyelets. Ankle boot silhouette. Leather lining and insole. Synthetic lug outsole. Ma
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To Boot New York Hoffman (Brown Bronx Lite) Men's Shoes

On sale - now $179.99 - was $325

The To Boot New York Hoffman is a perfect addition to any dress ensemble. Leather upper. Slip on loafer construction. Soft leather lining and insole. Durable synthetic outsole. Made in Italy. Measurements:Heel Height: 1 inWeight: 1 lbProduct measurements
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To Boot New York Hoffman (Navy Softy) Men's Shoes

On sale - now $179.99 - was $325

The To Boot New York Hoffman is a perfect addition to any dress ensemble. Leather upper. Slip on loafer construction. Soft leather lining and insole. Durable synthetic outsole. Made in Italy. Measurements:Heel Height: 1 inWeight: 1 lbProduct measurements
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To Boot New York Horst (Brown) Men's Shoes

On sale - now $209.99 - was $350

Refine your style with the timeless designs of To Boot New York. Suede leather upper with tonal stitching. Lace up front closure with blind eyelets. Chukka boot silhouette. Leather lining and insole. Lugged synthetic outsole. Made in Italy. Measurements:H
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To Boot New York Hunter (Brown) Men's Lace-up Boots

On sale - now $209.99 - was $350

Refine your style with the timeless designs of To Boot New York. Suede leather upper with tonal stitching. Lace up front closure with blind eyelets. Chukka boot silhouette. Leather lining and insole. Stylish crepe rubber outsole. Made in Italy. Measuremen
more...

To Boot New York Hunter (Dark Brown) Men's Lace-up Boots

On sale - now $209.99 - was $350

Refine your style with the timeless designs of To Boot New York. Suede leather upper with tonal stitching. Lace up front closure with blind eyelets. Chukka boot silhouette. Leather lining and insole. Stylish crepe rubber outsole. Made in Italy. Measuremen
more...

To Boot New York Jacobs (Black) Men's Shoes

On sale - now $89.99 - was $299

Perfect your ensemble with the noteworthy good looks of the To Boot New York Jacobs. Smooth leather upper with tonal stitching. Slip-on loafer construction. Leather vamp strap with penny keeper detail. Stitched toe accent. Leather lining and insole. Durab
more...

To Boot New York Jacobs (Dark Brown) Men's Shoes

On sale - now $164.99 - was $299

Perfect your ensemble with the noteworthy good looks of the To Boot New York Jacobs. Smooth leather upper with tonal stitching. Slip-on loafer construction. Leather vamp strap with penny keeper detail. Stitched toe accent. Leather lining and insole. Durab
more...

To Boot New York Jamison (Sigaro/Ebano Softy) Men's Shoes

On sale - now $222.59 - was $375

Stay casual and classy in the luxurious To Boot New York Jamison loafer. Soft suede upper. Vamp strap with penny keeper detail. Stitched accents. Moc toe. Plush leather lining and insole. Durable leather outsole with stacked heel. Made in Italy. Measureme
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To Boot New York Jax (Black) Men's Shoes

On sale - now $239.99 - was $398

Refine your style with the timeless designs of To Boot New York. Smooth leather upper with tonal stitching. Inside zip closure. Cross foot strap with buckle closure. Leather lining and insole. Durable leather and rubber outsole. Made in Italy. Measurement
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To Boot New York Jax (Dark Brown) Men's Shoes

On sale - now $239.99 - was $398

Refine your style with the timeless designs of To Boot New York. Smooth leather upper with tonal stitching. Inside zip closure. Cross foot strap with buckle closure. Leather lining and insole. Durable leather and rubber outsole. Made in Italy. Measurement
more...

To Boot New York Josh (Black) Men's Lace-up Boots

On sale - now $179.99 - was $299

Refine your style with the timeless designs of To Boot New York. Suede leather upper with tonal stitching. Lace up front closure with blind eyelets. Chukka boot silhouette. Leather lining and insole. Durable rubber outsole. Made in Italy. Measurements:Hee
more...

To Boot New York Kiefer (Cuoio CH Maremma) Men's Shoes

On sale - now $214.99 - was $475

The Kiefer is a great wingtip with a classic style and a modern edge! Leather upper. Slip-on. Stitched and brogue detailing. Distressed appeal. Burnished toe. Stacked heel. Leather lining and insole. Leather outsole. Made in Italy and imported. Measuremen
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To Boot New York Liam (Bordo 433 Parmadoc) Men's Shoes

On sale - now $234.99 - was $425

Create a clean and classic look in the fashion forward To Boot New York Liam. Burnished leather upper with tonal stitching. Adjustable strap at vamp with buckle closure. Rich leather lining and insole. Durable leather outsole with stacked heel. Made in It
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To Boot New York Lyle (Bianco Bott) Men's Shoes

On sale - now $161.99 - was $295

The Lyle by To Boot New York is a casual yet classy loafer for the man about town. Textured leather upper. Slip on construction. Stitched details. Moc toe. Leather lining and insole. Flexible man-made outsole. Made in Italy. Measurements:Heel Height: 1 4
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To Boot New York Lyle (Cocco Indaco Nabuk ST) Men's Shoes

On sale - now $161.99 - was $295

The Lyle by To Boot New York is a casual yet classy loafer for the man about town. Textured leather upper. Slip on construction. Stitched details. Moc toe. Leather lining and insole. Flexible man-made outsole. Made in Italy. Measurements:Heel Height: 1 4
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To Boot New York Lyle (Cocco Nero Nabuk ST) Men's Shoes

On sale - now $161.99 - was $295

The Lyle by To Boot New York is a casual yet classy loafer for the man about town. Textured leather upper. Slip on construction. Stitched details. Moc toe. Leather lining and insole. Flexible man-made outsole. Made in Italy. Measurements:Heel Height: 1 4
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To Boot New York Mickey (Dark Brown) Men's Shoes

On sale - now $239.99 - was $398

Refine your style with the timeless designs of To Boot New York. Suede upper with tonal stitching and perforated details. Lace up front closure with metal eyelets. Perforated toe detail. Leather lining and insole. Lugged synthetic outsole. Made in Italy.
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To Boot New York Moore (Black) Men's Shoes

On sale - now $236.99 - was $395

Stay classy in the refined looks of the To Boot New York Moore. Smooth leather upper with tonal stitching. Slip-on loafer construction. Leather vamp strap with penny keeper detail. Stitched toe accent. Leather lining and insole. Genuine leather outsole. M
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To Boot New York Newcomb (Black) Men's Lace-up Boots

On sale - now $236.99 - was $395

Refine your style with the timeless designs of To Boot New York. Smooth leather upper with tonal stitching. Lace up front closure with metal eyelets. Chukka boot silhouette. Leather lining and insole. Lugged synthetic outsole. Made in Italy. Measurements:
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To Boot New York Newcomb (Tan) Men's Lace-up Boots

On sale - now $236.99 - was $395

Refine your style with the timeless designs of To Boot New York. Smooth leather upper with tonal stitching. Lace up front closure with metal eyelets. Chukka boot silhouette. Leather lining and insole. Lugged synthetic outsole. Made in Italy. Measurements:
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To Boot New York Parke (Black Parma) Men's Shoes

On sale - now $190.41 - was $395

Please note, this style runs large. To Boot New York suggests you order a size smaller than your normal size. For example, if you normally wear a size 10, order a size 9. Bring comfort and faultless style to your look with these elegant loafers. Leather u
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To Boot New York Parke (Tek Spec Parma) Men's Shoes

On sale - now $236.99 - was $395

Please note, this style runs large. To Boot New York suggests you order a size smaller than your normal size. For example, if you normally wear a size 10, order a size 9. Bring comfort and faultless style to your look with these elegant loafers. Leather u
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To Boot New York Peters (Marrone 55 Parma Spec) Men's Shoes

On sale - now $206.99 - was $375

Dress for success in the handsome details of the To Boot New York Peters loafer. Sumptuous leather upper with tonal stitching. Slip on loafer construction. Soft leather lining and insole. Genuine leather outsole with stacked heel. Made in Italy. Measureme
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To Boot New York Phillip (Sigaro 336 Hummer) Men's Shoes

On sale - now $206.99 - was $375

Slip into the Phillip to feel comfort and express your unique style. Oiled Italian suede upper. Hand stitched apron vamp. Slip-on construction. Stitched and brogue detailing. Leather lining and insole. Rubber outsole with signature map of NYC. Made in Ita
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To Boot New York Preston (Black) Men's Shoes

On sale - now $164.99 - was $299

Create a stylish air with the To Boot New York Preston. Leather upper with tonal stitching. Slip-on loafer construction. Leather vamp strap with penny keeper detail. Stitched moc toe. Leather lining and insole. Durable synthetic outsole. Made in Italy. Me
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To Boot New York Preston (Brown) Men's Shoes

On sale - now $164.99 - was $299

Create a stylish air with the To Boot New York Preston. Leather upper with tonal stitching. Slip-on loafer construction. Leather vamp strap with penny keeper detail. Stitched moc toe. Leather lining and insole. Durable synthetic outsole. Made in Italy. Me
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To Boot New York Preston (Cognac) Men's Shoes

On sale - now $164.99 - was $299

Create a stylish air with the To Boot New York Preston. Leather upper with tonal stitching. Slip-on loafer construction. Leather vamp strap with penny keeper detail. Stitched moc toe. Leather lining and insole. Durable synthetic outsole. Made in Italy. Me
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To Boot New York Rafael (Dark Brown) Men's Shoes

On sale - now $209.99 - was $350

Refine your style with the timeless designs of To boot New York. Suede leather upper with tonal stitching. Cross foot strap with buckle closure. Leather lining and insole. Durable synthetic outsole. Made in Italy. Measurements:Heel Height: 1 inWeight: 1 l
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To Boot New York Reid (Nero Diver) Men's Shoes

On sale - now $112.5 - was $375

Perfect your tailored look in the sleek To Boot New York Reid. Leather upper with tonal stitching. Leather vamp strap with penny keeper detail. Slip on loafer construction. Soft leather lining and insole. Textured man-made and leather outsole. Made in Ita
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To Boot New York Reid (T. Moro 25 Diver) Men's Shoes

On sale - now $206.99 - was $375

Perfect your tailored look in the sleek To Boot New York Reid. Leather upper with tonal stitching. Leather vamp strap with penny keeper detail. Slip on loafer construction. Soft leather lining and insole. Textured man-made and leather outsole. Made in Ita
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To Boot New York Scott (Trapper Cognac) Men's Shoes

On sale - now $284.99 - was $475

Refine your style with the timeless designs of To Boot New York. Smooth leather upper with tonal stitching. Inside zip closure. Plain toe ankle boot silhouette. Leather lining and insole. Durable leather and synthetic outsole. Made in Italy. Measurements:
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To Boot New York Stern (Black) Men's Shoes

On sale - now $179.99 - was $299

Refine your style with the timeless designs of To Boot New York. Smooth leather upper with tonal stitching. Slip-on loafer construction. Stitched toe detail. Leather vamp strap with metallic hardware. Leather lining and insole. Textured synthetic outsole.
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To Boot New York Terrence (Cognac M13 Diver Tinto) Men's Shoes

On sale - now $206.99 - was $375

Grace your feet with sumptuous style in the To Boot New York Terrence loafer. Leather upper with tonal stitching. Slip on construction. Woven lace and eyelet detail at collar. Moc toe. Leather lining and insole. Durable synthetic outsole. Made in Italy. M
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To Boot New York Terrence (T Moro 25 Diver Tinto) Men's Shoes

On sale - now $206.99 - was $375

Grace your feet with sumptuous style in the To Boot New York Terrence loafer. Leather upper with tonal stitching. Slip on construction. Woven lace and eyelet detail at collar. Moc toe. Leather lining and insole. Durable synthetic outsole. Made in Italy. M
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To Boot New York Trevor (Blue 61 Vragano) Men's Shoes

On sale - now $206.99 - was $375

The Trevor from To Boot New York is the perfect any-occasion loafer that will look amazing dressed up or with a casual outfit. Genuine calf skin leather upper. Leather lining and insole. Venetian-style plain vamp moccasin loafer. Leather outsole. Made in
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To Boot New York Trevor (Cognac 58 Vragano) Men's Shoes

On sale - now $206.99 - was $375

The Trevor from To Boot New York is the perfect any-occasion loafer that will look amazing dressed up or with a casual outfit. Genuine calf skin leather upper. Leather lining and insole. Venetian-style plain vamp moccasin loafer. Leather outsole. Made in
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To Boot New York Wayne (Black) Men's Shoes

On sale - now $164.99 - was $299

The Wayne is a handsome shoe that offers stately luxury and comfort. Suede upper with stitched moc toe. Slip-on loafer construction. Leather vamp strap with metallic detail. Leather lining and insole. Leather and synthetic outsole. Made in Italy and impor
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