Massimo Matteo Men's Casual Shoes and Sneakers

Men's fashion shoes, casual shoes and sneakers by Massimo Matteo. The kind of shoes that you'd live in if you could or if your boss, customers or clients would let you, then again, maybe they won't notice....

 Previous page    |    Next page
Prices correct at time of writing - subject to change

Massimo Matteo 5-Eye Bal Medallion (Black) Men
Massimo Matteo 5-Eye Bal Medallion (Black) Men's Shoes
On sale - now $96.95 - was $175

Massimo Matteo 5-Eye Bal Medallion (Bordo) Men
Massimo Matteo 5-Eye Bal Medallion (Bordo) Men's Shoes
On sale - now $157.5 - was $175

Massimo Matteo 5-Eye Cap Toe (Black) Men
Massimo Matteo 5-Eye Cap Toe (Black) Men's Lace Up Wing Tip Shoes
$169

Massimo Matteo 5-Eye Cap Toe (Bordo) Men
Massimo Matteo 5-Eye Cap Toe (Bordo) Men's Lace Up Wing Tip Shoes
On sale - now $76.05 - was $169

Massimo Matteo 5-Eye Cap Toe (Brandy/Burnish Toe) Men
Massimo Matteo 5-Eye Cap Toe (Brandy/Burnish Toe) Men's Lace Up Wing Tip Shoes
On sale - now $89.57 - was $169

Massimo Matteo 5-Eye Oxford (Black) Men
Massimo Matteo 5-Eye Oxford (Black) Men's Shoes
On sale - now $145.68 - was $169

Massimo Matteo 6-Eye Bal Cap Toe (Black) Men
Massimo Matteo 6-Eye Bal Cap Toe (Black) Men's Lace Up Cap Toe Shoes
On sale - now $143.1 - was $159

Massimo Matteo 6-Eye Bal Cap Toe (Brown) Men
Massimo Matteo 6-Eye Bal Cap Toe (Brown) Men's Lace Up Cap Toe Shoes
On sale - now $99.22 - was $159

Massimo Matteo 6-Eye Bal Cap Toe (Tan) Men
Massimo Matteo 6-Eye Bal Cap Toe (Tan) Men's Lace Up Cap Toe Shoes
On sale - now $110.99 - was $159

Massimo Matteo 6-Eye Wing Tip (Black) Men
Massimo Matteo 6-Eye Wing Tip (Black) Men's Lace Up Wing Tip Shoes
On sale - now $110.99 - was $159

Massimo Matteo 6-Eye Wing Tip (Bordo) Men
Massimo Matteo 6-Eye Wing Tip (Bordo) Men's Lace Up Wing Tip Shoes
On sale - now $110.99 - was $159

Massimo Matteo 6-Eye Wing Tip (Tan) Men
Massimo Matteo 6-Eye Wing Tip (Tan) Men's Lace Up Wing Tip Shoes
On sale - now $110.99 - was $159

Massimo Matteo Almansa Lace-Up (Black) Men
Massimo Matteo Almansa Lace-Up (Black) Men's Shoes
On sale - now $87.75 - was $195

Massimo Matteo Almansa Lace-Up (Castano) Men
Massimo Matteo Almansa Lace-Up (Castano) Men's Shoes
On sale - now $122.85 - was $195

Massimo Matteo Almansa Moccasin Bit (Castano) Men
Massimo Matteo Almansa Moccasin Bit (Castano) Men's Shoes
On sale - now $117 - was $195

Massimo Matteo Almansa Single Monk (Black) Men
Massimo Matteo Almansa Single Monk (Black) Men's Shoes
On sale - now $175.5 - was $195

Massimo Matteo Almansa Single Monk (Castano) Men
Massimo Matteo Almansa Single Monk (Castano) Men's Shoes
On sale - now $175.99 - was $195

Massimo Matteo Almansa Single Monk (Forest Green) Men
Massimo Matteo Almansa Single Monk (Forest Green) Men's Shoes
On sale - now $146.64 - was $195

Massimo Matteo Almansa Slip-On (Black) Men
Massimo Matteo Almansa Slip-On (Black) Men's Shoes
On sale - now $156 - was $195

Massimo Matteo Ankle Strap Sandal (Black) Men
Massimo Matteo Ankle Strap Sandal (Black) Men's Sandals
On sale - now $84.99 - was $105

Massimo Matteo Ankle Strap Sandal (Marrone) Men
Massimo Matteo Ankle Strap Sandal (Marrone) Men's Sandals
On sale - now $94.99 - was $105

Massimo Matteo Bal Plain Toe (Black) Men
Massimo Matteo Bal Plain Toe (Black) Men's Lace Up Cap Toe Shoes
On sale - now $115.5 - was $165

Massimo Matteo Bal Plain Toe (Burnished Tan) Men
Massimo Matteo Bal Plain Toe (Burnished Tan) Men's Lace Up Cap Toe Shoes
On sale - now $87.48 - was $165

Massimo Matteo Bit Driver (Whiskey) Men
Massimo Matteo Bit Driver (Whiskey) Men's Slip on Shoes
On sale - now $47.99 - was $69

Massimo Matteo Bit Strap Driver (Black) Men
Massimo Matteo Bit Strap Driver (Black) Men's Shoes
$59

Massimo Matteo Bit Strap Driver (Whiskey) Men
Massimo Matteo Bit Strap Driver (Whiskey) Men's Shoes
$59

Massimo Matteo Bona Fide Penny Loafer (Black) Men
Massimo Matteo Bona Fide Penny Loafer (Black) Men's Shoes
On sale - now $76.01 - was $89

Massimo Matteo Bona Fide Penny Loafer (Burgundy) Men
Massimo Matteo Bona Fide Penny Loafer (Burgundy) Men's Shoes
On sale - now $53.4 - was $89

Massimo Matteo Bona Fide Wing Tip (Anil) Men
Massimo Matteo Bona Fide Wing Tip (Anil) Men's Shoes
On sale - now $40.05 - was $89

Massimo Matteo Bona Fine Cap Toe (Black) Men
Massimo Matteo Bona Fine Cap Toe (Black) Men's Shoes
On sale - now $69.06 - was $89

Massimo Matteo Bona Fine Cap Toe (Bronze) Men
Massimo Matteo Bona Fine Cap Toe (Bronze) Men's Shoes
On sale - now $57.85 - was $89

Massimo Matteo Boogie Down Velvet Loafer (Black Velvet) Men
Massimo Matteo Boogie Down Velvet Loafer (Black Velvet) Men's Shoes
On sale - now $116.61 - was $195

Massimo Matteo Braided Tie Driver (Havana/Cafe) Men
Massimo Matteo Braided Tie Driver (Havana/Cafe) Men's Shoes
On sale - now $67.5 - was $75

Massimo Matteo Buckle Slip-On (Black) Men
Massimo Matteo Buckle Slip-On (Black) Men's Slip on Shoes
On sale - now $135.96 - was $165

Massimo Matteo Buckle Slip-On (Brandy) Men
Massimo Matteo Buckle Slip-On (Brandy) Men's Slip on Shoes
On sale - now $88.77 - was $165

Massimo Matteo Collapsible Back Bit Driver (Burnished Tan) Men
Massimo Matteo Collapsible Back Bit Driver (Burnished Tan) Men's Shoes
On sale - now $71.4 - was $85

Massimo Matteo Collapsible Back Bit Driver (Navy) Men
Massimo Matteo Collapsible Back Bit Driver (Navy) Men's Shoes
On sale - now $67.99 - was $85

Massimo Matteo Collapsible Back Bit Driver (White) Men
Massimo Matteo Collapsible Back Bit Driver (White) Men's Shoes
On sale - now $44.76 - was $85

Massimo Matteo Comfort Lace-Up (Black) Men
Massimo Matteo Comfort Lace-Up (Black) Men's Shoes
On sale - now $46.14 - was $79

Massimo Matteo Comfort Lace-Up (Cafe Pineo) Men
Massimo Matteo Comfort Lace-Up (Cafe Pineo) Men's Shoes
On sale - now $44.04 - was $79

Massimo Matteo Comfort Slide (Marrone) Men
Massimo Matteo Comfort Slide (Marrone) Men's Sandals
On sale - now $107.1 - was $119

Massimo Matteo Croco Driver 19 (Black) Men
Massimo Matteo Croco Driver 19 (Black) Men's Shoes
On sale - now $32.9 - was $59

Massimo Matteo Dante Cap Toe Bal (Black) Men
Massimo Matteo Dante Cap Toe Bal (Black) Men's Shoes
On sale - now $105 - was $175

Massimo Matteo Dante Cap Toe Bal (Burnished Tan) Men
Massimo Matteo Dante Cap Toe Bal (Burnished Tan) Men's Shoes
$175

Massimo Matteo Dbl Monk Cap Toe (Black) Men
Massimo Matteo Dbl Monk Cap Toe (Black) Men's Slip on Shoes
$159

Massimo Matteo Dbl Monk Cap Toe (Brandy) Men
Massimo Matteo Dbl Monk Cap Toe (Brandy) Men's Slip on Shoes
On sale - now $127.99 - was $159

Massimo Matteo Desk Single Monk (Black) Men
Massimo Matteo Desk Single Monk (Black) Men's Shoes
On sale - now $105 - was $175

Massimo Matteo Desk Single Monk (Bordo) Men
Massimo Matteo Desk Single Monk (Bordo) Men's Shoes
On sale - now $157.5 - was $175

Massimo Matteo Desk Single Monk (Brandy) Men
Massimo Matteo Desk Single Monk (Brandy) Men's Shoes
On sale - now $126.7 - was $175

Massimo Matteo Desk Single Monk (Navy) Men
Massimo Matteo Desk Single Monk (Navy) Men's Shoes
On sale - now $144.9 - was $175

Massimo Matteo Driver With Bit (Black Pitstop w/ Bit) Men
Massimo Matteo Driver With Bit (Black Pitstop w/ Bit) Men's Flat Shoes
$69

Massimo Matteo Driver With Bit (Cognac Pitstop w/ Bit) Men
Massimo Matteo Driver With Bit (Cognac Pitstop w/ Bit) Men's Flat Shoes
$69

Massimo Matteo Drop Penny Loafer (Black 2) Men
Massimo Matteo Drop Penny Loafer (Black 2) Men's Slip on Shoes
On sale - now $142.99 - was $159

Massimo Matteo Drop Penny Loafer (Dark Brown 1) Men
Massimo Matteo Drop Penny Loafer (Dark Brown 1) Men's Slip on Shoes
On sale - now $152.99 - was $169

Massimo Matteo Drop Penny Loafer (Whisky) Men
Massimo Matteo Drop Penny Loafer (Whisky) Men's Slip on Shoes
On sale - now $143.1 - was $159

Massimo Matteo Florencia Penny Driver (Black) Men
Massimo Matteo Florencia Penny Driver (Black) Men's Slip on Shoes
$59

Massimo Matteo Florencia Penny Driver (Brown) Men
Massimo Matteo Florencia Penny Driver (Brown) Men's Slip on Shoes
$59

Massimo Matteo Florencia Penny Driver (Whiskey) Men
Massimo Matteo Florencia Penny Driver (Whiskey) Men's Slip on Shoes
On sale - now $52.99 - was $59

Massimo Matteo Formal Velvet Loafer (Black Patent) Men
Massimo Matteo Formal Velvet Loafer (Black Patent) Men's Shoes
On sale - now $109.99 - was $155

Massimo Matteo Gladiator with Buckle Strap (Black) Men
Massimo Matteo Gladiator with Buckle Strap (Black) Men's Shoes
$119

Massimo Matteo Huarache (Black) Men
Massimo Matteo Huarache (Black) Men's Slip on Shoes
On sale - now $87.99 - was $125

Massimo Matteo Huarache (Marrone) Men
Massimo Matteo Huarache (Marrone) Men's Slip on Shoes
On sale - now $99.99 - was $125

Massimo Matteo Huarache (T. Moro) Men
Massimo Matteo Huarache (T. Moro) Men's Slip on Shoes
$125

Massimo Matteo Lace Driver 17 (Bronze) Men
Massimo Matteo Lace Driver 17 (Bronze) Men's Slip-on Dress Shoes
On sale - now $41.22 - was $75

Massimo Matteo Latego Driver (Black) Men
Massimo Matteo Latego Driver (Black) Men's Shoes
On sale - now $71.1 - was $79

Massimo Matteo Latego Driver (Cafe) Men
Massimo Matteo Latego Driver (Cafe) Men's Shoes
On sale - now $55.3 - was $79

Massimo Matteo Leather Slide with Bit (Black) Men
Massimo Matteo Leather Slide with Bit (Black) Men's Shoes
$95

Massimo Matteo Leather Slide with Bit (White) Men
Massimo Matteo Leather Slide with Bit (White) Men's Shoes
$95

Massimo Matteo Leather Thong Sandal (Black) Men
Massimo Matteo Leather Thong Sandal (Black) Men's Sandals
On sale - now $86.92 - was $99

Massimo Matteo Leather Thong Sandal (Marrone) Men
Massimo Matteo Leather Thong Sandal (Marrone) Men's Sandals
On sale - now $89.1 - was $99

Massimo Matteo Leather Thong Sandal (Navy Blue) Men
Massimo Matteo Leather Thong Sandal (Navy Blue) Men's Sandals
$99

Massimo Matteo Leather Thong Sandal (Rosso) Men
Massimo Matteo Leather Thong Sandal (Rosso) Men's Sandals
$99

Massimo Matteo Leather Thong Sandal (T. Moro) Men
Massimo Matteo Leather Thong Sandal (T. Moro) Men's Sandals
$99

Massimo Matteo Leather Thong Sandal (Verde) Men
Massimo Matteo Leather Thong Sandal (Verde) Men's Sandals
$99

Massimo Matteo Leather/Nubuck Tie Driver (Navy) Men
Massimo Matteo Leather/Nubuck Tie Driver (Navy) Men's Shoes
On sale - now $41.4 - was $69

Massimo Matteo Leather/Nubuck Tie Driver (Red) Men
Massimo Matteo Leather/Nubuck Tie Driver (Red) Men's Shoes
On sale - now $41.4 - was $69

Massimo Matteo Loafer 17 (Black) Men
Massimo Matteo Loafer 17 (Black) Men's Slip on Shoes
On sale - now $115.5 - was $165

Massimo Matteo Mocc Toe Penny (Black 3) Men
Massimo Matteo Mocc Toe Penny (Black 3) Men's Slip on Shoes
On sale - now $101.4 - was $169

Massimo Matteo New Penny Classic (Black) Men
Massimo Matteo New Penny Classic (Black) Men's Slip on Shoes
On sale - now $50.34 - was $89

Massimo Matteo Patent Oxford (Black Patent) Men
Massimo Matteo Patent Oxford (Black Patent) Men's Shoes
On sale - now $115.99 - was $165

Massimo Matteo Penny Driver (Havana) Men
Massimo Matteo Penny Driver (Havana) Men's Flat Shoes
On sale - now $55.3 - was $79

Massimo Matteo Perf Bal Cap Toe (Black) Men
Massimo Matteo Perf Bal Cap Toe (Black) Men's Shoes
On sale - now $112.53 - was $165

Massimo Matteo Perf Bal Cap Toe (Tan) Men
Massimo Matteo Perf Bal Cap Toe (Tan) Men's Shoes
On sale - now $87.78 - was $165

Massimo Matteo Perf Bal Wing Tip (Black) Men
Massimo Matteo Perf Bal Wing Tip (Black) Men's Shoes
On sale - now $134.64 - was $165

Massimo Matteo Perf Bal Wing Tip (Brandy) Men
Massimo Matteo Perf Bal Wing Tip (Brandy) Men's Shoes
On sale - now $94.05 - was $165

Massimo Matteo Perf Double Monk (Black) Men
Massimo Matteo Perf Double Monk (Black) Men's Shoes
On sale - now $118.3 - was $169

Massimo Matteo Perf Double Monk (Brandy) Men
Massimo Matteo Perf Double Monk (Brandy) Men's Shoes
On sale - now $152.1 - was $169

Massimo Matteo Perf Double Monk (Tan) Men
Massimo Matteo Perf Double Monk (Tan) Men's Shoes
On sale - now $137.57 - was $169

Massimo Matteo Perf Nubuck Driver (Black) Men
Massimo Matteo Perf Nubuck Driver (Black) Men's Slip on Shoes
$65

Massimo Matteo Perf Nubuck Driver (Navy) Men
Massimo Matteo Perf Nubuck Driver (Navy) Men's Slip on Shoes
On sale - now $39 - was $65

Massimo Matteo Perf Penny Moc (Black) Men
Massimo Matteo Perf Penny Moc (Black) Men's Shoes
On sale - now $45 - was $75

Massimo Matteo Perf Penny Moc (Havana) Men
Massimo Matteo Perf Penny Moc (Havana) Men's Shoes
On sale - now $60 - was $75

Massimo Matteo Perf Penny Moc (Navy) Men
Massimo Matteo Perf Penny Moc (Navy) Men's Shoes
On sale - now $59.1 - was $75

Massimo Matteo Pitstop Penny Driver (Brown) Men
Massimo Matteo Pitstop Penny Driver (Brown) Men's Slip on Shoes
$59

Massimo Matteo Pitstop Penny Driver (Cognac) Men
Massimo Matteo Pitstop Penny Driver (Cognac) Men's Slip on Shoes
On sale - now $53.1 - was $59

Massimo Matteo Rope Bit Driver (Cafe) Men
Massimo Matteo Rope Bit Driver (Cafe) Men's Slip-on Dress Shoes
On sale - now $31.05 - was $69

Massimo Matteo Single Monk Cap Toe (Black) Men
Massimo Matteo Single Monk Cap Toe (Black) Men's Shoes
On sale - now $152.99 - was $169

Massimo Matteo Single Monk Cap Toe (Burnished Brandy) Men
Massimo Matteo Single Monk Cap Toe (Burnished Brandy) Men's Shoes
On sale - now $135.99 - was $169

Massimo Matteo Slip-On Bit Classic 18 (Bordo/Marinho) Men
Massimo Matteo Slip-On Bit Classic 18 (Bordo/Marinho) Men's Slip on Shoes
$89

Massimo Matteo Smoking Slipper (Leopard) Men
Massimo Matteo Smoking Slipper (Leopard) Men's Shoes
On sale - now $95.4 - was $159

Massimo Matteo Suede Nubuck Penny (Castor) Men
Massimo Matteo Suede Nubuck Penny (Castor) Men's Slip on Shoes
$79

Massimo Matteo Suede Penny Loafer (T. Moro Suede) Men
Massimo Matteo Suede Penny Loafer (T. Moro Suede) Men's Slip on Shoes
On sale - now $85.44 - was $159

Massimo Matteo Suede Tie Driver (Black Suede) Men
Massimo Matteo Suede Tie Driver (Black Suede) Men's Shoes
On sale - now $45 - was $75

Massimo Matteo Suede Tie Driver (Military Green Suede) Men
Massimo Matteo Suede Tie Driver (Military Green Suede) Men's Shoes
On sale - now $54 - was $75

Massimo Matteo Suede Tie Driver (Navy Suede) Men
Massimo Matteo Suede Tie Driver (Navy Suede) Men's Shoes
On sale - now $67.5 - was $75

Massimo Matteo Thong with Buckle Strap (Black) Men
Massimo Matteo Thong with Buckle Strap (Black) Men's Shoes
$95

Massimo Matteo Tonal Penny Driver (Burnished Tan Leather) Men
Massimo Matteo Tonal Penny Driver (Burnished Tan Leather) Men's Slip on Shoes
On sale - now $47.4 - was $79

Massimo Matteo Trancoso (Black) Men
Massimo Matteo Trancoso (Black) Men's Sandals
On sale - now $34.99 - was $49

Massimo Matteo Two Band Slide Sandal (Black) Men
Massimo Matteo Two Band Slide Sandal (Black) Men's Shoes
$95

Massimo Matteo Two-Strap Buckle Sandal (Black) Men
Massimo Matteo Two-Strap Buckle Sandal (Black) Men's Shoes
$99

Massimo Matteo Velvet Cap Toe Oxford (Black Velvet) Men
Massimo Matteo Velvet Cap Toe Oxford (Black Velvet) Men's Shoes
On sale - now $110.99 - was $159

Massimo Matteo Velvet Cap Toe Oxford (Burgundy Velvet) Men
Massimo Matteo Velvet Cap Toe Oxford (Burgundy Velvet) Men's Shoes
On sale - now $110.99 - was $159

Massimo Matteo Velvet Cap Toe Oxford (Grey Velvet) Men
Massimo Matteo Velvet Cap Toe Oxford (Grey Velvet) Men's Shoes
On sale - now $110.99 - was $159

Massimo Matteo Velvet Loafer (Black Velvet) Men
Massimo Matteo Velvet Loafer (Black Velvet) Men's Shoes
On sale - now $139.5 - was $155

Massimo Matteo Velvet Slip-On (Black) Men
Massimo Matteo Velvet Slip-On (Black) Men's Slip on Shoes
On sale - now $124.99 - was $155

Massimo Matteo Velvet Slip-On (Burgundy) Men
Massimo Matteo Velvet Slip-On (Burgundy) Men's Slip on Shoes
On sale - now $110.99 - was $159

Massimo Matteo Venetian Driver (Cafe) Men
Massimo Matteo Venetian Driver (Cafe) Men's Slip on Shoes
$65

Massimo Matteo Venetian Driver (Camel Nubuck) Men
Massimo Matteo Venetian Driver (Camel Nubuck) Men's Slip on Shoes
$65

Massimo Matteo Venetian Driver (Whiskey) Men
Massimo Matteo Venetian Driver (Whiskey) Men's Slip on Shoes
$65

Massimo Matteo Venetian Driver 19 (Black) Men
Massimo Matteo Venetian Driver 19 (Black) Men's Shoes
$75

Massimo Matteo Venetian Driver 19 (Burnished Tan) Men
Massimo Matteo Venetian Driver 19 (Burnished Tan) Men's Shoes
On sale - now $67.99 - was $75

Massimo Matteo Woven Bit Driver (Cinza) Men
Massimo Matteo Woven Bit Driver (Cinza) Men's Shoes
On sale - now $52.99 - was $75

Massimo Matteo Woven Slip-On (Tan) Men
Massimo Matteo Woven Slip-On (Tan) Men's Slip on Shoes
On sale - now $62.3 - was $89

Massimo Matteo Wrapped Bit Driver (Cafe) Men
Massimo Matteo Wrapped Bit Driver (Cafe) Men's Shoes
On sale - now $33.75 - was $75

Massimo Matteo Wrapped Bit Slip-On (Black Nappa) Men
Massimo Matteo Wrapped Bit Slip-On (Black Nappa) Men's Slip on Shoes
On sale - now $149.99 - was $165