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  • 226 Items
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Steve Madden Men's Harros Leather Chukka BootsMen's Harros Leather Chukka Boots

Steve MaddenMen's Harros Leather Chukka Boots

Internet Exclusive
Only size 13 available
Rated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 stars(2)
Timberland Men's Redwood Edge Leather Lace Up BootsMen's Redwood Edge Leather Lace Up Boots

TimberlandMen's Redwood Edge Leather Lace Up Boots

Extended Sizes
Johnston & Murphy Men's Reeve Leather Chelsea Dress BootsMen's Reeve Leather Chelsea Dress Boots

Johnston & MurphyMen's Reeve Leather Chelsea Dress Boots

Extended Sizes
Marc Nolan Men's Aiden Patent Leather Tortoise Print Combat BootsMen's Aiden Patent Leather Tortoise Print Combat Boots

Marc NolanMen's Aiden Patent Leather Tortoise Print Combat Boots

Internet Exclusive
Extended Sizes
Birkenstock Men's Stalon Nubuck Chelsea BootsMen's Stalon Nubuck Chelsea Boots

BirkenstockMen's Stalon Nubuck Chelsea Boots

Only size 12, 13 available
Danner Men's Waterproof Suede Mountain 600 4.5" BootsMen's Waterproof Suede Mountain 600 4.5" Boots

DannerMen's Waterproof Suede Mountain 600 4.5" Boots

Extended Sizes
Rated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 stars(2)
Skechers Men's Slip-ins Relaxed Fit: Respected 2.0 - Hagler BootsMen's Slip-ins Relaxed Fit: Respected 2.0 - Hagler Boots

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

Extended Sizes
Johnston & Murphy Collection Men's Hartford Leather Plain Toe BootsCollection Men's Hartford Leather Plain Toe Boots

Johnston & MurphyCollection Men's Hartford Leather Plain Toe Boots

Rated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 stars(1)
Men's Harros Leather Chukka Boots

PLACEHOLDERMen's Harros Leather Chukka Boots

Internet Exclusive
Only size 13 available
Rated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 stars(2)

SorelMen's Madson II Waterproof Leather Chukka Boots

Internet Exclusive
Extended Sizes
Rated 4.375 out of 5 starsRated 4.375 out of 5 starsRated 4.375 out of 5 starsRated 4.375 out of 5 starsRated 4.375 out of 5 stars(88)

Josef SeibelMen's Earl 12 Leather Chelsea Boots

PLACEHOLDERMen's Harros Leather Chukka Boots

Internet Exclusive
Only size 13 available
Rated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 stars(2)

BornMen's Nigel Suede Lace-Up Boots

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

ALIGNMen's Eddy Waterproof Leather Lace Up Boots

PLACEHOLDERMen's Harros Leather Chukka Boots

Internet Exclusive
Only size 13 available
Rated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 stars(2)

Cole HaanMen's ØriginalGrand CitySpectre Leather Chelsea Boots

Internet Exclusive

PikolinosMen's Vigo Leather Lace Up Zip Ankle Boots

Internet Exclusive

PLACEHOLDERMen's Harros Leather Chukka Boots

Internet Exclusive
Only size 13 available
Rated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 stars(2)

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)

Dune LondonMen's Matchin Leather Chelsea Boots

Internet Exclusive

Steve MaddenMen's Daviston Lace Up Leather Chukka Boots

Internet Exclusive
Extended Sizes

TimberlandMen's Redwood Falls Waterproof Leather Chukka Boots

Internet Exclusive
Extended Sizes
Rated 4.3387 out of 5 starsRated 4.3387 out of 5 starsRated 4.3387 out of 5 starsRated 4.3387 out of 5 starsRated 4.3387 out of 5 stars(62)

AriatMen's Wexford Waterproof Chelsea Boots

Rated 4.541 out of 5 starsRated 4.541 out of 5 starsRated 4.541 out of 5 starsRated 4.541 out of 5 starsRated 4.541 out of 5 stars(244)

AriatMen's Barrett Leather Boots

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

To Boot New YorkMen's Largo Chelsea Boots

Internet Exclusive

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)

Donald PlinerMen's Ashford Leather Chelsea Boots

Internet Exclusive
Extended Sizes

DannerMen's Bull Run Leather 6" Chelsea Boots

Extended Sizes

Twisted XMen's Moc Toe Leather Lace Up Boots

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

Johnston & MurphyMens Barrett Suede Zip Boots

Extended Sizes
Rated 2 out of 5 starsRated 2 out of 5 starsRated 2 out of 5 starsRated 2 out of 5 starsRated 2 out of 5 stars(1)

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

Internet Exclusive

SorelMen's Slabtown 62 Moc Waterproof Boots

Internet Exclusive
Extended Sizes
Rated 4.4211 out of 5 starsRated 4.4211 out of 5 starsRated 4.4211 out of 5 starsRated 4.4211 out of 5 starsRated 4.4211 out of 5 stars(38)

Twisted XMen's Waterproof Driving Moccasins Chukka Boots

Internet Exclusive
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)

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)

SorelMen's Cyprus Waterproof Leather Boots

Internet Exclusive
Extended Sizes

Johnston & MurphyMen's Calder 175th Anniversary Leather Chelsea Boots

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

Twisted XMen's Driving Leather Moc Toe Chukka Boots

Extended Sizes

Bruno MagliMen's Raging Leather Boots

Internet Exclusive

Dan PostMen's Ka Western Boots

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

Dr. MartensMen's Hardie Chelsea Boots

Extended Sizes
Rated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 stars(6)

ALDOMen's Farrell Leather Lace Up Boots

Internet Exclusive
Extended Sizes

Johnston & MurphyCollection Men's Hartford Waxed Suede Chelsea Boots

DannerMen's Logger Moc 917 GTX Waterproof Nubuck Leather Boots

Internet Exclusive
Extended Sizes

Bed StuMen's Michelangelo Rustic Leather Chelsea Boots

Internet Exclusive
Only size 8.5, 11.5 available

ALIGNMen's Ryder Weatherproof Suede Boots

Internet Exclusive

Johnston & MurphyCollection Men's Hartford Suede Plain Toe Boots

Internet Exclusive

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

Internet Exclusive

Dune LondonMen's Matias Leather Ankle Boots

Internet Exclusive

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)

ALIGNMen's Rangley Leather Chelsea Boots

Internet Exclusive

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

Internet Exclusive
Extended Sizes

AriatMen's Plano Western Boots

Internet Exclusive
Rated 3.9412 out of 5 starsRated 3.9412 out of 5 starsRated 3.9412 out of 5 starsRated 3.9412 out of 5 starsRated 3.9412 out of 5 stars(17)

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

Internet Exclusive

AriatMen's Heritage Roper Western Boots

Internet Exclusive
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 Jack Wool Cap Toe Boots

Internet Exclusive
Rated 4.8685 out of 5 starsRated 4.8685 out of 5 starsRated 4.8685 out of 5 starsRated 4.8685 out of 5 starsRated 4.8685 out of 5 stars(1194)

Johnston & MurphyCollection Men's Flynch Suede Chelsea Boots

Internet Exclusive
Extended Sizes

Dan PostMen's Abram Western Boots

Extended Sizes

FryeMen's Paul Leather Cap Toe Lace Up Boots

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

AriatMen's Maverick Western Five Row Stitch Boots

Internet Exclusive
Rated 4 out of 5 starsRated 4 out of 5 starsRated 4 out of 5 starsRated 4 out of 5 starsRated 4 out of 5 stars(2)

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)

ALIGNMen's Rangley Suede Chelsea 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)

Ted Baker LondonMen's Blackburn Leather Brogue Wingtip 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)

Dan PostMen's Winslow 11" Leather Western Boots

Internet Exclusive
Extended Sizes

ALIGNMen's Rivers Weatherproof Oiled Leather Flannel Lined Winter Boots

Internet Exclusive

Dune LondonMen's Saltwood Leather Cap Toe Chelsea Boots

Internet Exclusive

Twisted XMen's Slip-On Chukka Leather Driving Moccasin Boots

Internet Exclusive
Extended Sizes
Only size 13 available
Rated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 stars(2)

Twisted XMen's Chukka Driving Moccasins

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

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

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

ALDOMen's Zeddy Suede Chelsea Boots

Internet Exclusive
Extended Sizes

ALDOMen's Walton Leather Lace Up Booties

Internet Exclusive
Extended Sizes

AriatMen's Bomber Rambler Recon Western Boots

Internet Exclusive
Only size 11.5 available
Rated 4.4932 out of 5 starsRated 4.4932 out of 5 starsRated 4.4932 out of 5 starsRated 4.4932 out of 5 starsRated 4.4932 out of 5 stars(146)

TaftMen's Rome Bottega Suede Cap Toe Boots

Internet Exclusive

Dune LondonMen's Smoky Leather Casual Ankle Boots

Internet Exclusive

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

Internet Exclusive
Extended Sizes

Dan PostMen's Storms Eye 11" Waterproof Leather Composite Toe Work Boots

Extended Sizes

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

Internet Exclusive

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

Internet Exclusive
Extended Sizes

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

Internet Exclusive
Extended Sizes
Only size 10, 11 available

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

Extended Sizes

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

Internet Exclusive
Extended Sizes

UGGMen's Classic Suede Family Matching Short Boots

Extended Sizes
Rated 4.4 out of 5 starsRated 4.4 out of 5 starsRated 4.4 out of 5 starsRated 4.4 out of 5 starsRated 4.4 out of 5 stars(5)

Dr. MartensMen's Combs Fold-Down Boots

Extended Sizes
Only size 11, 13 available
Rated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 stars(8)

BornMen's Harrison Leather Chukka Boots

Internet Exclusive
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)

Polo Ralph LaurenMen's Ranger Suede and Twill Patch Detail Boots

Permanently Reduced
Orig.
Now
Extended Sizes
Rated 2.6 out of 5 starsRated 2.6 out of 5 starsRated 2.6 out of 5 starsRated 2.6 out of 5 starsRated 2.6 out of 5 stars(5)

MerrellMen's Moab 3 Mid Waterproof Hiking Boots

Permanently Reduced
Orig.
Now
Extended Sizes
Rated 4.3528 out of 5 starsRated 4.3528 out of 5 starsRated 4.3528 out of 5 starsRated 4.3528 out of 5 starsRated 4.3528 out of 5 stars(428)

UGGMen's Chukka Lug Suede Boots

Permanently Reduced
Orig.
Now
Extended Sizes

Johnston & MurphyMen's XC Flex Raleigh Leather Chelsea Boots

Permanently Reduced
Orig.
Now
Extended Sizes
Rated 4.6842 out of 5 starsRated 4.6842 out of 5 starsRated 4.6842 out of 5 starsRated 4.6842 out of 5 starsRated 4.6842 out of 5 stars(57)

Steve MaddenMen's Jotting Leather Contrast Stitch Cap Toe Boots

Permanently Reduced
Orig.
Now
Rated 4.8333 out of 5 starsRated 4.8333 out of 5 starsRated 4.8333 out of 5 starsRated 4.8333 out of 5 starsRated 4.8333 out of 5 stars(6)

UGGMen's Lug Chukka Boots

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

Johnston & MurphyMen's XC+Parker Waterproof Leather Chukka Boots

Permanently Reduced
Orig.
Now
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(5)

BornMen's Brock Distressed Suede Boots

Permanently Reduced
Orig.
Now
Extended Sizes
Rated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 stars(9)

Cole HaanMen's Muir Waterproof Suede Moc Toe Boots

Permanently Reduced
Orig.
Now
Internet Exclusive

Flag LTD.Men's Marsen Cap Toe Leather Lace-Up Hiker Boots

Permanently Reduced
Orig.
Now
Dillard's Exclusive
Rated 4.7059 out of 5 starsRated 4.7059 out of 5 starsRated 4.7059 out of 5 starsRated 4.7059 out of 5 starsRated 4.7059 out of 5 stars(17)

Flag LTD.Men's Garrett Leather Plain Toe Boots

Permanently Reduced
Orig.
Now
Dillard's Exclusive
Rated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 stars(1)

Steve MaddenMen's Hatford Leather Chelsea Boots

Permanently Reduced
Orig.
Now
Extended Sizes

Steve MaddenMen's Tabriz Lace Up Leather Chukka Boots

Permanently Reduced
Orig.
Now
Extended Sizes

Steve MaddenMen's Hatford Suede Chelsea Boots

Permanently Reduced
Orig.
Now
Extended Sizes
Rated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 stars(3)
Born Men's Reed Leather BootsMen's Reed Leather Boots

BornMen's Reed Leather Boots

Permanently Reduced
Orig.
Now
Extended Sizes
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