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  • 194 Items
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Johnston & Murphy Men's Upton Leather Chukka BootsMen's Upton Leather Chukka Boots

Johnston & MurphyMen's Upton Leather Chukka Boots

Extended Sizes
Cole Haan Men's Chamberlin Water Resistant Nubuck Chelsea BootsMen's Chamberlin Water Resistant Nubuck Chelsea Boots

Cole HaanMen's Chamberlin Water Resistant Nubuck Chelsea Boots

Internet Exclusive
Dr. Martens Men's Combs Tech II Utility BootsMen's Combs Tech II Utility Boots

Dr. MartensMen's Combs Tech II Utility Boots

Internet Exclusive
Extended Sizes
Sorel Men's CYPRUS Waterproof Suede Chelsea BootsMen's CYPRUS Waterproof Suede Chelsea Boots

SorelMen's CYPRUS Waterproof Suede Chelsea Boots

Internet Exclusive
Extended Sizes
Born Men's Harrison Leather Chukka BootsMen's Harrison Leather Chukka Boots

BornMen's Harrison Leather Chukka Boots

Extended Sizes
Rated 4.697 out of 5 starsRated 4.697 out of 5 starsRated 4.697 out of 5 starsRated 4.697 out of 5 starsRated 4.697 out of 5 stars(33)
Pikolinos Men's York Leather Lace Up BootsMen's York Leather Lace Up Boots

PikolinosMen's York Leather Lace Up Boots

Ariat Men's Clean Country Suede Chukka BootsMen's Clean Country Suede Chukka Boots

AriatMen's Clean Country Suede Chukka Boots

Rated 4.35 out of 5 starsRated 4.35 out of 5 starsRated 4.35 out of 5 starsRated 4.35 out of 5 starsRated 4.35 out of 5 stars(20)
Born Men's Ryker Leather BootsMen's Ryker Leather Boots

BornMen's Ryker Leather Boots

Rated 3.5 out of 5 starsRated 3.5 out of 5 starsRated 3.5 out of 5 starsRated 3.5 out of 5 starsRated 3.5 out of 5 stars(2)
Men's Upton Leather Chukka Boots

PLACEHOLDERMen's Upton Leather Chukka Boots

Extended Sizes

Josef SeibelMen's Earl 12 Leather Chelsea Boots

ALIGNMen's Rivers Weatherproof Tumbled Leather Boots

PLACEHOLDERMen's Upton Leather Chukka Boots

Extended Sizes

Dan PostMen's Kingsly 11" Caiman Square Toe Western Boots

Internet Exclusive
Extended Sizes

Steve MaddenMen's Daviston Lace Up Leather Chukka Boots

Internet Exclusive
Extended Sizes

PLACEHOLDERMen's Upton Leather Chukka Boots

Extended Sizes

TimberlandMen's Redwood Edge Leather Lace Up Boots

Extended Sizes

Polo Ralph LaurenMen's Ranger Suede and Plaid Wool Boots

Internet Exclusive
Extended Sizes
Rated 1.0 out of 5 starsRated 1.0 out of 5 starsRated 1.0 out of 5 starsRated 1.0 out of 5 starsRated 1.0 out of 5 stars(2)

PLACEHOLDERMen's Upton Leather Chukka Boots

Extended Sizes

Johnston & MurphyMen's Reeve Leather Chelsea Dress Boots

Extended Sizes

Polo Ralph LaurenMen's Ranger Suede Multi Boots

Internet Exclusive
Rated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 stars(3)

SkechersMen's Slip-ins Relaxed Fit: Respected 2.0 - Hagler Boots

Extended Sizes
Rated 4.7526 out of 5 starsRated 4.7526 out of 5 starsRated 4.7526 out of 5 starsRated 4.7526 out of 5 starsRated 4.7526 out of 5 stars(97)

Dr. MartensMen's 2976 Leather Family Matching Chelsea Boots

Rated 4.9 out of 5 starsRated 4.9 out of 5 starsRated 4.9 out of 5 starsRated 4.9 out of 5 starsRated 4.9 out of 5 stars(10)

Cole HaanMen's Chamberlin Water Resistant Nubuck Chukka Boots

Internet Exclusive

Johnston & MurphyCollection Men's Hartford Leather Plain Toe Boots

Internet Exclusive

Marc NolanMen's Aiden Patent Leather Tortoise Print Combat Boots

Internet Exclusive
Extended Sizes

Johnston & MurphyCollection Men's Hartford Leather Chelsea Dress Boots

Rated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 stars(1)

BirkenstockMen's Highwood Leather Chelsea Boots

TimberlandMen's Newmarket Chukka Leather Boots

Extended Sizes
Rated 4.8 out of 5 starsRated 4.8 out of 5 starsRated 4.8 out of 5 starsRated 4.8 out of 5 starsRated 4.8 out of 5 stars(15)

Cole HaanMen's Chamberlin Water Resistant Nubuck Cap Toe Boots

Internet Exclusive

L.L.BeanMen's Eco Bay Nubuck Chukka Boots

Polo Ralph LaurenMen's Ranger Suede Patch Detail Boots

Internet Exclusive
Rated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 stars(1)

Marc NolanMen's Belmont Appaloosa Cow Print Brogue Wingtip Combat Boots

Extended Sizes

Cole HaanMen's Chamberlin Water Resistant Suede Cap Toe Boots

Internet Exclusive

Twisted XMen's ECO Moc-Toe Lace Up Boot

Rated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 stars(2)

ALDOMen's Collen Suede Chelsea Boots

Internet Exclusive
Extended Sizes

SorelMen's Slabtown 62 Six Waterproof Boots

Extended Sizes
Rated 4.6471 out of 5 starsRated 4.6471 out of 5 starsRated 4.6471 out of 5 starsRated 4.6471 out of 5 starsRated 4.6471 out of 5 stars(34)

To Boot New YorkMen's Largo Chelsea Boots

Internet Exclusive

Cole HaanMen's ØriginalGrand CitySpectre Leather Chelsea Boots

Internet Exclusive

Twisted XMen's 4" Woven Leather Boots

Extended Sizes
Rated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 stars(2)

Kurt Geiger LondonMen's Chiltern Leather Boots

Dan PostMen's Winslow 11" Leather Western Boots

Internet Exclusive
Extended Sizes

BornMen's Erik Leather Boots

Extended Sizes

Bruno MagliMen's Raging Leather Boots

Internet Exclusive

Cole HaanMen's Muir Waterproof Suede Moc Toe Boots

Internet Exclusive

PikolinosMen's Vigo Leather Lace Up Zip Ankle Boots

Internet Exclusive

Bed StuMen's Protege Distressed Leather Back Zip Combat Boots

Internet Exclusive
Extended Sizes

ALIGNMen's Ryder Weatherproof Leather Boots

AriatMen's Heritage Roper Western Boots

Extended Sizes
Rated 4.4523 out of 5 starsRated 4.4523 out of 5 starsRated 4.4523 out of 5 starsRated 4.4523 out of 5 starsRated 4.4523 out of 5 stars(283)

TaftMen's Rome Leather Cap Toe Boots

Internet Exclusive
Extended Sizes
Rated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 stars(1)

Johnston & MurphyCollection Men's Hartford Waxed Suede Chelsea Boots

Twisted XMen's Chukka Driving Moccasins

Internet Exclusive
Extended Sizes
Rated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 stars(1)

Bed StuMen's Lincoln Lace Up Leather Boots

Dan PostMen's Brutus 11" Python Snake Square Toe Western Boots

Internet Exclusive

Dune LondonMen's Call Leather Cap Toe Zip Buckle Hardware Boots

Internet Exclusive

ALIGNMen's Ryder Weatherproof Suede Boots

Internet Exclusive

Marc NolanMen's Dax Cow Print Pony Hair Chelsea Boots

Internet Exclusive
Extended Sizes

Twisted XMen's Driving Moccasin Chukka Boots

Internet Exclusive
Extended Sizes

FryeMen's Astor Leather Chukka Boots

Internet Exclusive
Rated 4.2308 out of 5 starsRated 4.2308 out of 5 starsRated 4.2308 out of 5 starsRated 4.2308 out of 5 starsRated 4.2308 out of 5 stars(13)

Cole HaanMen's Muir Leather Moc Toe Boots

Internet Exclusive

Donald PlinerMen's Ashford Leather Chelsea Boots

Internet Exclusive
Extended Sizes

Johnston & MurphyCollection Men's Hartford Suede Plain Toe Boots

Internet Exclusive

Bed StuMen's Illiad Leather Chukka Boots

Ted Baker LondonMen's Norwich Leather Chelsea Ankle Boots

Internet Exclusive
Extended Sizes

Dune LondonMen's Smoky Leather Casual Ankle Boots

Internet Exclusive

Twisted XMen's Driving Woven Leather Moccasin Chukka Boots

Extended Sizes
Rated 4.5 out of 5 starsRated 4.5 out of 5 starsRated 4.5 out of 5 starsRated 4.5 out of 5 starsRated 4.5 out of 5 stars(2)

AriatMen's Maverick Western Five Row Stitch Boots

Internet Exclusive
Rated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 stars(1)

TaftMen's Jack Wool Calfskin Cap Toe Braided Welt Detail Boots

Internet Exclusive
Extended Sizes
Rated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 stars(7)

Dan PostMen's Alamosa 11" Full Quill Ostrich Square Toe Western Boots

Internet Exclusive
Extended Sizes

AriatMen's Sport Freedom Western Boots

Internet Exclusive
Rated 4.3333 out of 5 starsRated 4.3333 out of 5 starsRated 4.3333 out of 5 starsRated 4.3333 out of 5 starsRated 4.3333 out of 5 stars(6)

ALDOMen's Zeddy Suede Chelsea Boots

Internet Exclusive
Extended Sizes

Ted Baker LondonMen's Blackburn Leather Brogue Wingtip Boots

Extended Sizes

Johnston & MurphyCollection Men's Flynch Suede Chelsea Boots

Internet Exclusive
Extended Sizes

ALIGNMen's Rangley Suede Chelsea Boots

Internet Exclusive

ALDOMen's Farrell Leather Lace Up Boots

Internet Exclusive
Extended Sizes

Dan PostMen's Murray 11" Bison Leather Square Toe Western Boots

Internet Exclusive

Dan PostMen's Abram Western Boots

Extended Sizes

Dune LondonMen's Saltwood Leather Cap Toe Chelsea Boots

Internet Exclusive

ALDOMen's Walton Leather Lace Up Booties

Internet Exclusive
Extended Sizes

ALIGNMen's Rangley Leather Chelsea Boots

Internet Exclusive

Dan PostMen's Saddlebred 11" Waterproof Leather Steel Toe Work Boots

Internet Exclusive
Extended Sizes

ALIGNMen's Rivers Weatherproof Oiled Leather Boots

Internet Exclusive

Dan PostMen's Sire 11" Waterproof Leather Steel Toe Work Boots

Internet Exclusive
Extended Sizes

TaftMen's Rome Bottega Suede Cap Toe Boots

Internet Exclusive

Dan PostMen's Cottonwood 13" Leather Round Toe Western Boots

Internet Exclusive

EastlandMen's Ethan 1955 Leather Boots

Internet Exclusive
Extended Sizes
Only size 9, 12 available

Twisted XMen's Moc Toe Leather Lace Up Boots

Rated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 stars(3)

UGGMen's Chukka Lug Suede Boots

Permanently Reduced
Orig.
Now
Extended Sizes

UGGMen's Chelsea Lug Suede Boots

Permanently Reduced
Orig.
Now
Extended Sizes

UGGMen's Neumel Crafted Regenerate Boots

Permanently Reduced
Orig.
Now

UGGMen's Lug Chukka Boots

Permanently Reduced
Orig.
Now
Extended Sizes
Rated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 stars(1)

Steve MaddenMen's Tabriz Lace Up Leather Chukka Boots

Permanently Reduced
Orig.
Now
Extended Sizes

Steve MaddenMen's Hatford Leather Chelsea Boots

Permanently Reduced
Orig.
Now
Extended Sizes

Steve MaddenMen's Salvatore Leather Lug Sole Boots

Permanently Reduced
Orig.
Now
Extended Sizes
Rated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 stars(4)

Steve MaddenMen's Hatford Suede Chelsea Boots

Permanently Reduced
Orig.
Now
Extended Sizes

ALIGNMen's Eddy Waterproof Leather Lace Up Boots

Limited Time Offer
Orig.
Now

Twisted XMen's Leather Lace-Up Chukka Driving Moccasins

Permanently Reduced
Orig.
Now
Extended Sizes
Rated 4.6667 out of 5 starsRated 4.6667 out of 5 starsRated 4.6667 out of 5 starsRated 4.6667 out of 5 starsRated 4.6667 out of 5 stars(3)

Johnston & MurphyMen's Larkin Leather Plain Toe Chukka Boots

Permanently Reduced
Orig.
Now
Extended Sizes

Steve MaddenMen's Duke Leather Chelsea Boots

Permanently Reduced
Orig.
Now
Extended Sizes

UGGMen's Classic Ultra Mini Wrap Tech Boots

Permanently Reduced
Orig.
Now
Internet Exclusive
Extended Sizes
Steve Madden Men's Aben Leather Chelsea BootsMen's Aben Leather Chelsea Boots

Steve MaddenMen's Aben Leather Chelsea Boots

Permanently Reduced
Orig.
Now
Internet Exclusive
  • 194 Items
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