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Bruin Plain Toe ...

$398 $198.90
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Bruin Plain Toe Chukka Boot

Clean lines and minimal detailing bring the ultimate in versatility to a plain-toe chukka boot styled simply with three-hole lacing and a polished finish. Style Name: To Boot New York Bruin Plain Toe Chukka Boot (Men). Style Number: 5645810 1. Available in stores.

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Bruin Plain Toe ...

$398 $198.90
Free shiping

Bruin Plain Toe Chukka Boot

Clean lines and minimal detailing bring the ultimate in versatility to a plain-toe chukka boot styled simply with three-hole lacing and a polished finish. Style Name: To Boot New York Bruin Plain Toe Chukka Boot (Men). Style Number: 5645810 1. Available in stores.

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Ives Suede Chels...

$375 $262.50
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Ives Suede Chelsea Boots

To Boot New York Men's Ives Suede Chelsea Boots

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Bondfield Leathe...

$450 $315
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Bondfield Leather Cap Toe Boots

To Boot New York Men's Bondfield Leather Cap Toe Boots

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Kipling Wingtip ...

$450 $224.98
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Kipling Wingtip Derby

Traditional broguing traces the contours and finishes the toe of a wardrobe-staple wingtip styled for versatility with classic derby lacing. Style Name: To Boot New York Kipling Wingtip Derby (Men). Style Number: 5561226. Available in stores.

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Amadora Cap Toe ...

$398 $198.98
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Amadora Cap Toe Oxford

A neat cap toe anchors the front of a handsome oxford that layers polished leather over suede for an updated take on a classic wardrobe staple. Style Name: To Boot New York Amadora Cap Toe Oxford (Men). Style Number: 5600072. Available in stores.

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Ludlum Cap Toe M...

$398 $198.98
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Ludlum Cap Toe Monk Shoe

Clean lines and simple detailing define a smartly polished shoe styled with a panhandle monk strap and a squared cap toe. Style Name: To Boot New York Ludlum Cap Toe Monk Shoe (Men). Style Number: 5480849. Available in stores.

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Haas Plain Toe D...

$395 $196.90
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Haas Plain Toe Derby

Lustrous, supple leather defines a charming Italian derby shaped in a clean-cut silhouette. Style Name: To Boot New York Haas Plain Toe Derby (Men). Style Number: 5645808. Available in stores.

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Hudson Cap Toe O...

$395 $196.90
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Hudson Cap Toe Oxford

Lustrous leather construction elevates a clean, charming oxford crafted in Italy and fitted with an arch support footbed. Style Name: To Boot New York Hudson Cap Toe Oxford (Men). Style Number: 5645811 1. Available in stores.

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Devries Penny Lo...

$395 $196.90
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Devries Penny Loafer

Lustrous leather elevates a charming Italian loafer in a clean, classic silhouette and fitted with a smart arch support footbed. Style Name: To Boot New York Devries Penny Loafer (Men). Style Number: 5645809. Available in stores.

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Hudson Cap Toe O...

$395 $196.90
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Hudson Cap Toe Oxford

Lustrous leather construction elevates a clean, charming oxford crafted in Italy and fitted with an arch support footbed. Style Name: To Boot New York Hudson Cap Toe Oxford (Men). Style Number: 5645811 1. Available in stores.

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Haas Plain Toe D...

$395 $196.90
Free shiping

Haas Plain Toe Derby

Lustrous, supple leather defines a charming Italian derby shaped in a clean-cut silhouette. Style Name: To Boot New York Haas Plain Toe Derby (Men). Style Number: 5645808. Available in stores.

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Devries Penny Lo...

$395 $196.90
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Devries Penny Loafer

Lustrous leather elevates a charming Italian loafer in a clean, classic silhouette and fitted with a smart arch support footbed. Style Name: To Boot New York Devries Penny Loafer (Men). Style Number: 5645809. Available in stores.

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Koning Double Bu...

$395 $196.90
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Koning Double Buckle Monk Shoe

Minimal detailing brings maximum versatility to a wardrobe-staple leather monk shoe styled with a plain cap toe and an unadorned, two-buckle monk strap. Style Name: To Boot New York Koning Double Buckle Monk Shoe (Men). Style Number: 5645448 1. Available in stores.

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Koning Double Bu...

$395 $196.90
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Koning Double Buckle Monk Shoe

Minimal detailing brings maximum versatility to a wardrobe-staple leather monk shoe styled with a plain cap toe and an unadorned, two-buckle monk strap. Style Name: To Boot New York Koning Double Buckle Monk Shoe (Men). Style Number: 5645448 1. Available in stores.

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Henri Cap Toe Bo...

$395 $196.90
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Henri Cap Toe Boot

Finely textured leather elevates a stylish Italian boot crafted with a cushioned arch support footbed for all-day comfort. Style Name: To Boot New York Henri Cap Toe Boot (Men). Style Number: 5412106 1. Available in stores.

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Koning Double Bu...

$395 $197.49
Free shiping

Koning Double Buckle Monk Shoe

Minimal detailing brings maximum versatility to a wardrobe-staple leather monk shoe styled with a plain cap toe and an unadorned, two-buckle monk strap. Style Name: To Boot New York Koning Double Buckle Monk Shoe (Men). Style Number: 5645448. Available in stores.

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Koning Double Bu...

$395 $197.49
Free shiping

Koning Double Buckle Monk Shoe

Minimal detailing brings maximum versatility to a wardrobe-staple leather monk shoe styled with a plain cap toe and an unadorned, two-buckle monk strap. Style Name: To Boot New York Koning Double Buckle Monk Shoe (Men). Style Number: 5645448. Available in stores.

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Caruso Plain Toe...

$395 $197.49
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Caruso Plain Toe Derby

Classic and simple, this wardrobe-staple derby is styled with a plain toe for easy-to-wear versatility and a crepe rubber sole for casual comfort. Style Name: To Boot New York Caruso Plain Toe Derby (Men). Style Number: 5480851. Available in stores.

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Hudson Cap Toe O...

$395 $197.49
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Hudson Cap Toe Oxford

Lustrous leather construction elevates a clean, charming oxford crafted in Italy and fitted with an arch support footbed. Style Name: To Boot New York Hudson Cap Toe Oxford (Men). Style Number: 5645811 1. Available in stores.

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Hudson Cap Toe O...

$395 $197.49
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Hudson Cap Toe O...

$395 $197.49
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Raleigh Apron To...

$350 $174.98
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'Buchanan' Plain...

$350 $174.98
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Raleigh Apron To...

$350 $174.98
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Henri Cap Toe Bo...

$395 $237.90
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Henri Cap Toe Bo...

$395 $237.90
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Knox Low Top Sne...

$325 $162.49
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Knox Low Top Sne...

$325 $162.49
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Norse Penny Loaf...

$298 $134.10
Free shiping

Benjamin Double ...

$350 $209.90
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'Barbados' Fishe...

$275 $137.49
Free shiping

Emmett Monk Stra...

$395 $284.71
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Hudson Leather C...

$395 $225
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Devries Leather ...

$395 $225
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Astoria Boots - ...

$398 $278.60
Free shiping

Rayburn Leather ...

$398 $278.60
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Harrison Side Zi...

$398 $278.60
Free shiping

Hank Leather Pla...

$395 $276.50
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Hendrick Perfora...

$375 $262.50
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Benjamin Leather...

$350 $245
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Jack Suede Buck ...

$350 $245
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Colman Slip-On S...

$350 $245
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Carlin Leather L...

$350 $245
Free shiping

Alek Leather Pen...

$350 $245
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Huston Lace Up S...

$350 $245
Free shiping

Alek Suede Loafe...

$350 $245
Free shiping

Britt Suede Low ...

$350 $245
Free shiping