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Sperry Top-Sider
Men's Boots

Men's boots by Sperry Top-Sider. There's something particularly satisfying about boots, proper footwear, especially when it's getting cooler.

Prices correct at time of writing - subject to change

Sperry Top-Sider 'Authentic Original - Boardwalk' Chukka Boot (Men)
$110

Rich Scotch-grain leather shapes a mid-cut chukka boot featuring hand-sewn construction and classic boat-shoe styling. A signature, Wave-siping sole offers superior wet/dry traction to effortlessly take you from brunch to boardwalk. Color(s): blue, oxbloo more...




Sperry Top-Sider 'Authentic Original' Chukka Boot (Men)
$110

Boat-shoe styling informs a hearty chukka boot crafted from durable leather and fitted with sharp rawhide lacing. Color(s): black. Brand: Sperry Top-Sider. Style Name: Sperry Top-Sider 'Authentic Original' Chukka Boot (Men). Style Number: 714140. more...




Sperry Top-Sider 'Authentic Original' Chukka Boot (Men)
$110

Rich, natural leather forms a hand-sewn chukka boot with cool nautical appeal. Color(s): brown, grey. Brand: Sperry Top-Sider. Style Name: Sperry Top-Sider 'Authentic Original' Chukka Boot (Men). Style Number: 714167. more...




Sperry Top-Sider 'Authentic Original' Chukka Boot (Men) Brown 9 M
$110

Rich, natural leather forms a hand-sewn chukka boot with cool nautical appeal. Color(s): brown, grey. Brand: Sperry Top-Sider. Style Name: Sperry Top-Sider 'Authentic Original' Chukka Boot (Men). Style Number: 714167. more...




Sperry Top-Sider 'Avenue' Rain Boot (Men)
$110

A waterproof rubber sole grounds a hearty rain boot with rugged, outdoorsy appeal. Color(s): black, navy/ tan. Brand: Sperry Top-Sider. Style Name: Sperry Top-Sider 'Avenue' Rain Boot (Men). Style Number: 467780. more...




Sperry Top-Sider 'Avenue' Waterproof Mid High Duck Boot
$99.95

Classic boat shoe details blend with waterproof duck boot construction for a weather-ready boot that protects you even when the temperature takes a dive. Color(s): dark tan/ brown. Brand: Sperry Top-Sider. Style Name: Sperry Top-Sider 'Avenue' Waterproof more...




Sperry Top-Sider 'Bahama' Boot
On sale - now $49.96 - was $99.95

Boat shoe styling influences a winterized boot lined with soft faux shearling for warmth and comfort. Color(s): black. Brand: Sperry Top-Sider. Style Name: Sperry Top-Sider 'Bahama' Boot. Style Number: 683737. more...




Sperry Top-Sider 'Bahama' Moc Toe Boot
On sale - now $42.47 - was $84.95

Richly colored wool panels frame an eye-catching boot laced with rawhide for a rustic touch. Color(s): brown. Brand: Sperry Top-Sider. Style Name: Sperry Top-Sider 'Bahama' Moc Toe Boot. Style Number: 683721. more...




Sperry Top-Sider 'Bahama' Moc Toe Boot
On sale - now $44.96 - was $89.95

Tough canvas shapes a nautical-style boot laced with rawhide for a rustic touch. Color(s): chino, grey. Brand: Sperry Top-Sider. Style Name: Sperry Top-Sider 'Bahama' Moc Toe Boot. Style Number: 967715. more...




Sperry Top-Sider 'Bahama' Moc Toe Boot (Men)
On sale - now $39.96 - was $79.95

Washed-out canvas forms a nautical-style boot laced with rawhide for a rustic touch. Color(s): black. Brand: Sperry Top-Sider. Style Name: Sperry Top-Sider 'Bahama' Moc Toe Boot (Men). Style Number: 414655. more...




Sperry Top-Sider 'Billfish Ultralite' Moc Toe Boot (Men)
$110

Lightweight construction defines a rustically inspired boot touched with boat-shoe styling. Color(s): dark brown. Brand: Sperry Top-Sider. Style Name: Sperry Top-Sider 'Billfish Ultralite' Moc Toe Boot (Men). Style Number: 467719. more...




Sperry Top-Sider 'Cloud' Chukka Sneaker (Men)
$79.95

Soft suede and sharp leather trim define a cool sneaker imbued with the spirit of a classic chukka boot. Color(s): grey, grey suede. Brand: Sperry Top-Sider. Style Name: Sperry Top-Sider 'Cloud' Chukka Sneaker (Men). Style Number: 714142. more...




Sperry Top-Sider 'Cloud' Chukka Sneaker (Men) Grey Suede 7 M
$79.95

Soft suede and sharp leather trim define a cool sneaker imbued with the spirit of a classic chukka boot. Color(s): grey, grey suede. Brand: Sperry Top-Sider. Style Name: Sperry Top-Sider 'Cloud' Chukka Sneaker (Men). Style Number: 714142. more...




Sperry Top-Sider 'Cold Bay' Short Weatherproof Duck Boot
$120

A good-looking duck boot features waterproof, seam-sealed construction and warm Thinsulate lining to keep your feet dry and warm in the nastiest of weather. Rated for temperatures as low as -25 degrees F. Color(s): amaretto. Brand: Sperry Top-Sider. Style more...




Sperry Top-Sider 'Drifter' Chukka Boot
$64.95

A herringbone texture coats a cool chukka set on a bubble-texture sole. Color(s): black/ white print. Brand: Sperry Top-Sider. Style Name: Sperry Top-Sider 'Drifter' Chukka Boot. Style Number: 616925 2. more...




Sperry Top-Sider 'Gold Cup - Bellingham' Chukka Boot (Men)
$195

The Gold Cup Collection takes the inimitable Sperry style to the next level with hand-burnished leather, meticulous design and classic appeal for a touch of shine to seal the deal. Fine style and distinct charm mark a handsome chukka boot fitted with an A more...




Sperry Top-Sider 'Gold Cup - Bellingham' Chukka Boot (Men) Tan 10 M
$195

The Gold Cup Collection takes the inimitable Sperry style to the next level with hand-burnished leather, meticulous design and classic appeal for a touch of shine to seal the deal. Fine style and distinct charm mark a handsome chukka boot fitted with an A more...




Sperry Top-Sider 'Gold Cup' Chukka Boot
$170

Durable full-grain leather shapes a mid-cut chukka boot splashed with boat-shoe styling and featuring genuine hand-sewn construction and a slip-resistant rubber sole. Color(s): dark brown. Brand: Sperry Top-Sider. Style Name: Sperry Top-Sider 'Gold Cup' C more...




Sperry Top-Sider 'Gold Cup' Chukka Boot
On sale - now $84.98 - was $170

Durable full-grain leather shapes a mid-cut chukka boot splashed with boat-shoe styling and featuring genuine hand-sewn construction and a slip-resistant rubber sole. Color(s): grey. Brand: Sperry Top-Sider. Style Name: Sperry Top-Sider 'Gold Cup' Chukka more...




Sperry Top-Sider 'Harbor' Canvas Chukka Boot
$99.95

A traditional chukka boot is updated for warm weather in classic canvas. Color(s): brown canvas. Brand: Sperry Top-Sider. Style Name: Sperry Top-Sider 'Harbor' Canvas Chukka Boot. Style Number: 967347. more...




Sperry Top-Sider 'Harbor' Canvas Chukka Boot
$99.95

A traditional chukka boot is updated for warm weather in classic canvas. Color(s): navy. Brand: Sperry Top-Sider. Style Name: Sperry Top-Sider 'Harbor' Canvas Chukka Boot. Style Number: 720224. more...




Sperry Top-Sider - A/O Chukka Neon (Dark Brown/Red)
On sale - now $54.99 - was $100

Sperry Top-Sider - A/O Chukka Neon (Dark Brown/Red) - The original boat shoe silhouette adapted for a more urban feel - it's the A/O Chukka Neon from Sperry Top-Sider. Clean and contemporary, this chukka is ready for that big city gathering or mixer anyti more...

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Sperry Top-Sider - A/O Chukka Neon (Grey/Orange)
On sale - now $44.99 - was $100

Sperry Top-Sider - A/O Chukka Neon (Grey/Orange) - The original boat shoe silhouette adapted for a more urban feel - it's the A/O Chukka Neon from Sperry Top-Sider. Clean and contemporary, this chukka is ready for that big city gathering or mixer anytime! more...

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Sperry Top-Sider - A/O Chukka Neon (Oatmeal/Citron)
On sale - now $54.99 - was $100

Sperry Top-Sider - A/O Chukka Neon (Oatmeal/Citron) - The original boat shoe silhouette adapted for a more urban feel - it's the A/O Chukka Neon from Sperry Top-Sider. Clean and contemporary, this chukka is ready for that big city gathering or mixer anyti more...

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Sperry Top-Sider - A/O Coastal Craftsmen 7-Eye (Dark Brown/Tan)
On sale - now $76.99 - was $140

Sperry Top-Sider - A/O Coastal Craftsmen 7-Eye (Dark Brown/Tan) - The A/O Coastal Craftsmen 7-Eye from Sperry Top-Sider is ideal for weekend travel or just kicking back at night with friends. Rich leather upper with hand-sewn construction for long-lasting more...

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Sperry Top-Sider - Avenue Duck Boot (Black)
$110

Sperry Top-Sider - Avenue Duck Boot (Black) - No matter if you are braving the freezing sea air or the the cold city streets, the Avenue Duck Boot from Sperry Top-Sider will keep you cozy and steady on your feet! Upper made of a leather shaft and rubber f more...

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Sperry Top-Sider - Bahama Chukka Suede (Black Suede 2)
On sale - now $44.99 - was $80

Sperry Top-Sider - Bahama Chukka Suede (Black Suede 2) - Enjoy the sun and surf anywhere in the world with the Bahama Chukka Suede by Sperry Top-Sider. Leather and suede upper materials. Genuine hand-sewn construction offers the tru-moc experience for dur more...

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Sperry Top-Sider - Bahama Zipper Boot (Chino)
On sale - now $41.99 - was $90

Sperry Top-Sider - Bahama Zipper Boot (Chino) - The Bahama Zipper Boot by Sperry Top-Sider is great for casual wear with its relaxed and comfortable style. Canvas upper. Hand-sewn construction ensures durability and long-lasting wear. Comfortable textile more...

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Sperry Top-Sider - Billfish Ultralite Chukka Boot (Tan/Orange)
On sale - now $49.99 - was $110

Sperry Top-Sider - Billfish Ultralite Chukka Boot (Tan/Orange) - Whatever adventures you have planned for the day will be easily achieved with the stylish, lightweight, and incredibly comfortable Billfish Ultralite Chukka Boot from Sperry Top-Sider. Nubuc more...

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Sperry Top-Sider - Boat Oxford Chukka Boot (Burgundy Burnished)
On sale - now $61.99 - was $110

Sperry Top-Sider - Boat Oxford Chukka Boot (Burgundy Burnished) - This fall season make a fashion statement with the sleek and fashion forward design of the Sperry Top-Sider Boat Oxford Chukka Boot. Premium leather upper material. Lace-up closure provides more...

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Sperry Top-Sider - Bristol Chukka (Black)
$120

Sperry Top-Sider - Bristol Chukka (Black) - Enjoy the low-key sophistication of the Bristol Chukka from Sperry Top-Sider. Suede upper with leather trim. Lace-up closure with three sturdy metal eyelets for a secure and traditional fit. Breathable textile l more...

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Sperry Top-Sider - Bristol Chukka (Brown Buc)
$120

Sperry Top-Sider - Bristol Chukka (Brown Buc) - Enjoy the low-key sophistication of the Bristol Chukka from Sperry Top-Sider. Suede upper with leather trim. Lace-up closure with three sturdy metal eyelets for a secure and traditional fit. Breathable texti more...

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Sperry Top-Sider - Cold Bay Boot (Black/Amaretto)
$150

Sperry Top-Sider - Cold Bay Boot (Black/Amaretto) - Whether you're facing the frigid sea air or the icy cold urban streets, the Cold Bay Boot from Sperry Top-SiderR will keep you warm and protected against the cold elements. Stain and water-resistant leat more...

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Sperry Top-Sider - Cold Bay Boot (Brown/Tan)
$150

Sperry Top-Sider - Cold Bay Boot (Brown/Tan) - Whether you're facing the frigid sea air or the icy cold urban streets, the Cold Bay Boot from Sperry Top-SiderR will keep you warm and protected against the cold elements. Stain and water-resistant leather u more...

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Sperry Top-Sider - Cold Bay Boot (Navy/Dark Brown)
$150

Sperry Top-Sider - Cold Bay Boot (Navy/Dark Brown) - Whether you're facing the frigid sea air or the icy cold urban streets, the Cold Bay Boot from Sperry Top-SiderR will keep you warm and protected against the cold elements. Stain and water-resistant lea more...

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Sperry Top-Sider - Cold Bay Boot (Tan/Dark Brown)
On sale - now $77 - was $140

Sperry Top-Sider - Cold Bay Boot (Tan/Dark Brown) - Whether you're facing the frigid sea air or the icy cold urban streets, the Cold Bay Boot from Sperry Top-SiderR will keep you warm and protected against the cold elements. Stain and water-resistant leat more...

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Sperry Top-Sider - Drifter Chukka (Tan Stripe)
On sale - now $41.99 - was $65

Sperry Top-Sider - Drifter Chukka (Tan Stripe) - Head out to your next adventure in total comfort and style with the Drifter Chukka boot from Sperry Top-Sider. Cotton canvas upper for better breathability and comfort. Unique stitching detail featured alon more...

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Sperry Top-Sider - Gold Bellingham Chukka w/ASV (Tan Suede)
On sale - now $106.99 - was $195

Sperry Top-Sider - Gold Bellingham Chukka w/ASV (Tan Suede) - This Sperry Top-Sider chukka is perfect for both the office and even more casual events with friends. Leather upper. Traditional lacing for a preferred fit. Sperry's AntiShock and Vibration tec more...

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Sperry Top-Sider - Harbor Chukka Boot (Dark Grey)
$120

Sperry Top-Sider - Harbor Chukka Boot (Dark Grey) - With a balance of comfort and handsome, laid-back style, the Sperry Top-Sider Harbor Chukka Boot is truly a doozy! Premium leather upper in a classic chukka silhouette. Lace-up closure for a secure fit. more...

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Sperry Top-Sider - Sedona (Navy Suede)
On sale - now $49.99 - was $160

Sperry Top-Sider - Sedona (Navy Suede) - The Sperry Top-Sider Sedona will be an oasis in the desert that is your shoe wardrobe. Soft suede leather upper. Lace-up front closure features leather laces. Closed toe with moc stitching. Smooth leather lining an more...

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Sperry Top-Sider - Shipyard Rigger Boot (Black/Dark Grey Chambray)
On sale - now $82.5 - was $150

Sperry Top-Sider - Shipyard Rigger Boot (Black/Dark Grey Chambray) - Get ready to set sail when you slip into the rugged and reliable Sperry Shipyard Rigger Boot. Genuine handsewn construction for durable comfort. Combination full-grain leather and canvas more...

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Sperry Top-Sider - The Harbor Chukka Canvas (Brown Canvas)
On sale - now $64.99 - was $100

Sperry Top-Sider - The Harbor Chukka Canvas (Brown Canvas) - Relax into the easy style of the Harbor Chukka Canvas by the Sperry Top-Sider. Soft canvas upper. Genuine rawhide laces for a secure fit. The front part of the insole is canvas and the back part more...

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Sperry Top-Sider - The Harbor Chukka Canvas (Navy Canvas)
On sale - now $54.99 - was $100

Sperry Top-Sider - The Harbor Chukka Canvas (Navy Canvas) - Relax into the easy style of the Harbor Chukka Canvas by the Sperry Top-Sider. Soft canvas upper. Genuine rawhide laces for a secure fit. The front part of the insole is canvas and the back part more...

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Sperry Top-Sider By Jeffrey 'Sedona' Chukka Boot
On sale - now $98.98 - was $198

Exposed stitching and rawhide laces lend a moccasin feel to a soft suede chukka boot. Color(s): sand, tan suede. Brand: Sperry Top-Sider. Style Name: Sperry Top-Sider by Jeffrey 'Sedona' Chukka Boot. Style Number: 612757. more...



 

Men's Boots
by Manufacturer

adidas
Ahnu
Allen Edmonds
Ariat
Asolo
Baffin
Bates Footwear
Bates Riding Collection
Ben Sherman
Blundstone
Bogs
Born
BOSS
BRUNO MAGLI
Call it SPRING
Calvin Klein
Camper
Carhartt
Caterpillar
Chaco
Clarks
Cole Haan
Columbia
Crocs
Cushe
Danner
Dan Post
DC
Diesel
Dingo
Donald J Pliner
Dr Martens
Dr Martens Work
DSQUARED2
Dunham
Durango
DVS Shoe Company
Eastland
ECCO
Emerald by Element
Florsheim
Fratelli
Fred Perry
Frye
GBX
Generic Surplus
Geox
Giorgio Brutini
Harley Davidson
Hi Tec
Hunter
Hush Puppies
Irish Setter
JD Fisk
Jeffery West
John Varvatos
Kamik
Keen
Keen Utility
Kenneth Cole
Lacoste
Laredo
La Sportiva
Le Chameau
Lloyd
Lowa
Lucchese
Lugz
Magnanni
Magnum
Merrell
New Balance
Oakley
Old Gringo
OluKai
Original Penguin
Palladium
Pikolinos
Polo Ralph Lauren
Propet
Red Wing Heritage
Reef
RJ Colt
Robert Wayne
Rockport
Roper
RW by Robert Wayne
Salomon
Salvatore Ferragamo
Sanuk
Scarpa
SeaVees
Sebago
SKECHERS
SKECHERS Work
SOREL
Sperry Top Sider
Stacy Adams
Steptronic
Stetson
Steve Madden
Ted Baker
Teva
The North Face
Thorogood
Timberland
Timberland Boot Company
Timberland PRO
To Boot New York
Tommy Hilfiger
Tretorn
Tsubo
Tundra Boots
UGG
UGG Collection
Vasque
Vivobarefoot
Volcom
Wolverine
Zamberlan



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