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  • 231 Items
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Flag LTD. Men's Ayden Moc Toe Waterproof Leather Lace Up Chukka BootsMen's Ayden Moc Toe Waterproof Leather Lace Up Chukka Boots

Flag LTD.Men's Ayden Moc Toe Waterproof Leather Lace Up Chukka Boots

Dillard's Exclusive
Marc Nolan Men's Dax Patent Leather Chelsea BootsMen's Dax Patent Leather Chelsea Boots

Marc NolanMen's Dax Patent Leather Chelsea 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 & Murphy Men's Upton Leather Chelsea BootsMen's Upton Leather Chelsea Boots

Johnston & MurphyMen's Upton Leather Chelsea Boots

Extended Sizes
Rated 3.0 out of 5 starsRated 3.0 out of 5 starsRated 3.0 out of 5 starsRated 3.0 out of 5 starsRated 3.0 out of 5 stars(4)
Sorel Men's Slabtown 62 Moc Waterproof BootsMen's Slabtown 62 Moc Waterproof Boots

SorelMen's Slabtown 62 Moc Waterproof Boots

Internet Exclusive
Extended Sizes
Rated 4.4286 out of 5 starsRated 4.4286 out of 5 starsRated 4.4286 out of 5 starsRated 4.4286 out of 5 starsRated 4.4286 out of 5 stars(35)
Dingo Men's Road Trip Suede O-Ring Harness Hardware Lug Sole BootsMen's Road Trip Suede O-Ring Harness Hardware Lug Sole Boots

DingoMen's Road Trip Suede O-Ring Harness Hardware Lug Sole Boots

Internet Exclusive
Extended Sizes
Marc Nolan Men's Belmont Cow Print Wingtip Brogue Detail Combat BootsMen's Belmont Cow Print Wingtip Brogue Detail Combat Boots

Marc NolanMen's Belmont Cow Print Wingtip Brogue Detail Combat 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(1)
Twisted X Men's Slip-On Chukka Leather Driving Moccasin BootsMen's Slip-On Chukka Leather Driving Moccasin Boots

Twisted XMen's Slip-On Chukka Leather Driving Moccasin 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(2)
Dr. Martens Men's 1460 Classic Leather Family Matching Combat BootsMen's 1460 Classic Leather Family Matching Combat Boots

Dr. MartensMen's 1460 Classic Leather Family Matching Combat Boots

Extended Sizes
Rated 4.9211 out of 5 starsRated 4.9211 out of 5 starsRated 4.9211 out of 5 starsRated 4.9211 out of 5 starsRated 4.9211 out of 5 stars(38)
Men's Ayden Moc Toe Waterproof Leather Lace Up Chukka Boots

PLACEHOLDERMen's Ayden Moc Toe Waterproof Leather Lace Up Chukka Boots

Dillard's Exclusive

Twisted XMen's Chukka Hiker Waterproof 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)

Dr. MartensMen's Combs Leather Boots

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(33)

PLACEHOLDERMen's Ayden Moc Toe Waterproof Leather Lace Up Chukka Boots

Dillard's Exclusive

L.L.BeanMen's Portland Leather Chelsea Boots

Rated 4.1579 out of 5 starsRated 4.1579 out of 5 starsRated 4.1579 out of 5 starsRated 4.1579 out of 5 starsRated 4.1579 out of 5 stars(19)

Twisted XMen's Waterproof Driving Moccasins Chukka Boots

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)

PLACEHOLDERMen's Ayden Moc Toe Waterproof Leather Lace Up Chukka Boots

Dillard's Exclusive

SorelMen's Slabtown 62' Stoic Suede Chukka 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 & MurphyMen's Upton Leather Chukka Boots

Extended Sizes

PLACEHOLDERMen's Ayden Moc Toe Waterproof Leather Lace Up Chukka Boots

Dillard's Exclusive

Cole HaanMen's Chamberlin Water Resistant Nubuck Chelsea Boots

Internet Exclusive

TimberlandMen's Redwood Falls Waterproof Leather Chukka Boots

Internet Exclusive
Extended Sizes
Rated 4.3051 out of 5 starsRated 4.3051 out of 5 starsRated 4.3051 out of 5 starsRated 4.3051 out of 5 starsRated 4.3051 out of 5 stars(59)

Dr. MartensMen's Combs Tech II Utility Boots

Internet Exclusive
Extended Sizes

SorelMen's CYPRUS Waterproof Suede Chelsea Boots

Internet Exclusive
Extended Sizes

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)

PikolinosMen's York Leather Lace Up 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)

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)

Josef SeibelMen's Earl 12 Leather Chelsea Boots

ALIGNMen's Rivers Weatherproof Tumbled Leather Boots

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

DannerMen's Waterproof Suede Mountain 600 4.5" 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)

TimberlandMen's Redwood Edge Leather Lace Up Boots

Extended Sizes

AriatMen's Lookout Leather Chukka Boots

Only size 11 available
Rated 4.1493 out of 5 starsRated 4.1493 out of 5 starsRated 4.1493 out of 5 starsRated 4.1493 out of 5 starsRated 4.1493 out of 5 stars(67)

SorelMen's Scout 87' XT Waterproof Boots

Internet Exclusive
Extended Sizes
Rated 3.0 out of 5 starsRated 3.0 out of 5 starsRated 3.0 out of 5 starsRated 3.0 out of 5 starsRated 3.0 out of 5 stars(5)

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)

Johnston & MurphyMen's Reeve Leather Chelsea Dress Boots

Extended Sizes

BirkenstockMen's Uppsala Mid Suede Boots

AriatMen's Wexford Waterproof Chelsea Boots

Rated 4.5537 out of 5 starsRated 4.5537 out of 5 starsRated 4.5537 out of 5 starsRated 4.5537 out of 5 starsRated 4.5537 out of 5 stars(242)

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)

TimberlandMen's Redwood Falls Waterproof Cold Weather Boots

Internet Exclusive
Rated 4.6186 out of 5 starsRated 4.6186 out of 5 starsRated 4.6186 out of 5 starsRated 4.6186 out of 5 starsRated 4.6186 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

MerrellMen's Moab 3 Mid Waterproof Hiking Boots

Extended Sizes
Rated 4.3493 out of 5 starsRated 4.3493 out of 5 starsRated 4.3493 out of 5 starsRated 4.3493 out of 5 starsRated 4.3493 out of 5 stars(418)

Johnston & MurphyCollection Men's Hartford Leather Plain Toe Boots

Internet Exclusive

Dr. MartensMen's Hardie Chelsea 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(6)

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

AriatMen's Barrett Leather Boots

Extended Sizes
Rated 4.0 out of 5 starsRated 4.0 out of 5 starsRated 4.0 out of 5 starsRated 4.0 out of 5 starsRated 4.0 out of 5 stars(4)

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

SorelMen's Madson II Moc Toe Waterproof Boots

Internet Exclusive
Rated 4.6154 out of 5 starsRated 4.6154 out of 5 starsRated 4.6154 out of 5 starsRated 4.6154 out of 5 starsRated 4.6154 out of 5 stars(13)

SorelMen's Buxton Lite Lace Plus Waterproof Boots

Extended Sizes
Rated 4.0 out of 5 starsRated 4.0 out of 5 starsRated 4.0 out of 5 starsRated 4.0 out of 5 starsRated 4.0 out of 5 stars(7)

BornMen's Nigel Suede Lace-Up 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)

BirkenstockMen's Stalon Nubuck Chelsea Boots

Only size 12, 13 available

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

SorelMen's Carson Storm Waterproof Boots

Internet Exclusive
Rated 4.4286 out of 5 starsRated 4.4286 out of 5 starsRated 4.4286 out of 5 starsRated 4.4286 out of 5 starsRated 4.4286 out of 5 stars(7)

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)

Dune LondonMen's Matchin Leather Chelsea Boots

Internet Exclusive

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

COACHMen's Connor Signature Logo Coated Canvas and Leather Lace Up Boots

Internet Exclusive

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)

MerrellMen's Moab 3 Vista Mid Waterproof Mid Hikers

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(21)

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

Internet Exclusive
Extended Sizes
Ariat Men's Sport Freedom Western BootsMen's Sport Freedom Western Boots

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)
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