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  • 270 Items
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Steve Madden Men's Meeker Leather Chukka BootsMen's Meeker Leather Chukka Boots

Steve MaddenMen's Meeker Leather Chukka Boots

Internet Exclusive
Dune London Men's Matchin Leather Chelsea BootsMen's Matchin Leather Chelsea Boots

Dune LondonMen's Matchin Leather Chelsea Boots

Polo Ralph Lauren Men's Bryson Leather and Wool Cap Toe BootsMen's Bryson Leather and Wool Cap Toe Boots

Polo Ralph LaurenMen's Bryson Leather and Wool Cap Toe Boots

Internet Exclusive
Extended Sizes
Rated 4.0476 out of 5 starsRated 4.0476 out of 5 starsRated 4.0476 out of 5 starsRated 4.0476 out of 5 starsRated 4.0476 out of 5 stars(21)
Marc Nolan Men's Dante Leather Chelsea BootsMen's Dante Leather Chelsea Boots

Marc NolanMen's Dante Leather Chelsea Boots

Extended Sizes
Johnston & Murphy Mens XC Flex Daylen Chelsea BootsMens XC Flex Daylen Chelsea Boots

Johnston & MurphyMens XC Flex Daylen Chelsea Boots

Internet Exclusive
Marc Nolan Men's Dax Leather Western Chelsea BootsMen's Dax Leather Western Chelsea Boots

Marc NolanMen's Dax Leather Western Chelsea 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(3)
Ariat Men's Hybrid Low Boy BootsMen's Hybrid Low Boy Boots

AriatMen's Hybrid Low Boy Boots

Rated 4.713 out of 5 starsRated 4.713 out of 5 starsRated 4.713 out of 5 starsRated 4.713 out of 5 starsRated 4.713 out of 5 stars(223)
Frye Men's Paul Chukka Lite BootsMen's Paul Chukka Lite Boots

FryeMen's Paul Chukka Lite 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)
Men's Meeker Leather Chukka Boots

PLACEHOLDERMen's Meeker Leather Chukka Boots

Internet Exclusive

TecovasMen's The Doc Goat Leather Square Toe Cowboy Boots

Extended Sizes

Josef SeibelMen's Earl 04 Leather Lace Up Chukka 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(6)

PLACEHOLDERMen's Meeker Leather Chukka Boots

Internet Exclusive

BlundstoneMen's 550 Water Resistant Chelsea 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)

FryeMen's Paul Leather Zip Boots

Internet Exclusive
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(8)

PLACEHOLDERMen's Meeker Leather Chukka Boots

Internet Exclusive

Johnston & MurphyMen's Ripley Leather Zip Boots

Dr. MartensMen's 2976 Chelsea Boots

Extended Sizes
Rated 4.5208 out of 5 starsRated 4.5208 out of 5 starsRated 4.5208 out of 5 starsRated 4.5208 out of 5 starsRated 4.5208 out of 5 stars(48)

PLACEHOLDERMen's Meeker Leather Chukka Boots

Internet Exclusive

BornMen's Waterproof Leather Rex Boots

Internet Exclusive

Section XMen's Steven Leather Zip Chelsea Boots

Dillard's 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)

FryeMen's Paul Leather Chukka 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(2)

TecovasMen's The Doc Frontier Western 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(5)

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)

Cole HaanMen's Windham Grand Chelsea Waterproof Boots

Internet Exclusive

To Boot New YorkMen's Largo Chelsea Boots

Johnston & MurphyMen's XC+Durham Waterproof Leather Chelsea Boots

Extended Sizes
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)

Dan PostMen's Ringold 13" Teju Lizard Square Toe Western Boots

Internet Exclusive

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

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)

PikolinosMen's Vigo Leather Lace Up Zip Ankle Boots

Internet Exclusive

Twisted XMen's Driving Leather Moc Toe Chukka Boots

Extended Sizes
Rated 4.7143 out of 5 starsRated 4.7143 out of 5 starsRated 4.7143 out of 5 starsRated 4.7143 out of 5 starsRated 4.7143 out of 5 stars(7)

DingoMen's Bulls Eye Cow Print Calf Hair Western Boots

Internet Exclusive

Johnston & MurphyCollection Men's Hartford Leather Chelsea Dress Boots

Internet Exclusive
Rated 3.6667 out of 5 starsRated 3.6667 out of 5 starsRated 3.6667 out of 5 starsRated 3.6667 out of 5 starsRated 3.6667 out of 5 stars(3)

Cole HaanMen's Chamberlin Water Resistant Nubuck Chukka Boots

Dr. MartensMen's Combs Leather Boots

Internet Exclusive
Only size 8, 12 available
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)
See all 6 colors >

DingoMen's Workhorse Leather Snip Toe Western Boots

Internet Exclusive

Cole HaanMen's Chamberlin Water Resistant Nubuck Chelsea Boots

Marc NolanMen's Belmont Cow Print Wingtip Brogue Detail Combat 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)

Johnston & MurphyMen's Clint Leather Chukka Boots

Internet Exclusive

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

Internet Exclusive
Extended Sizes

TimberlandMen's Auburn Falls Waterproof Nubuck Chukka Boots

Internet Exclusive

ALIGNMen's Ryder Weatherproof Leather Boots

Internet Exclusive

DannerMen's Logger Moc 917 GTX Waterproof Nubuck Leather Boots

Internet Exclusive
Extended Sizes

Johnston & MurphyCollection Men's Hartford Leather Plain Toe Boots

Internet Exclusive
Rated 4.75 out of 5 starsRated 4.75 out of 5 starsRated 4.75 out of 5 starsRated 4.75 out of 5 starsRated 4.75 out of 5 stars(4)

FryeTyler Flex Leather Chelsea Boots

Internet Exclusive
Rated 3.2857 out of 5 starsRated 3.2857 out of 5 starsRated 3.2857 out of 5 starsRated 3.2857 out of 5 starsRated 3.2857 out of 5 stars(7)

DingoMen's Renegade Leather O-Ring Harness Buckle Snip Toe Moto Boots

Internet Exclusive

BornMen's Henry Chukka Boots

Steve MaddenMen's Devera Leather Chelsea Boots

Internet Exclusive

AriatMen's Spitfire Waterproof Leather Boots

Extended Sizes
Rated 4.5075 out of 5 starsRated 4.5075 out of 5 starsRated 4.5075 out of 5 starsRated 4.5075 out of 5 starsRated 4.5075 out of 5 stars(67)

Johnston & MurphyMen's Reeve Leather Chelsea Dress Boots

Extended Sizes

Johnston & MurphyMen's Britton Leather Boots

Internet Exclusive

UGGMen's Classic Ultra Mini Weather Hybrid Boots

Extended Sizes

AriatMen's Sport Rambler Western Boots

Extended Sizes
Rated 4.8118 out of 5 starsRated 4.8118 out of 5 starsRated 4.8118 out of 5 starsRated 4.8118 out of 5 starsRated 4.8118 out of 5 stars(85)

Johnston & MurphyMen's Conlin Leather Side Zip Boots

Internet Exclusive

Dr. MartensMen's 1460 Boots

Extended Sizes

BirkenstockMen's Highwood Chelsea Boots

Internet Exclusive

L.L.BeanL.L. Bean Men's Bean Boot 6.5 Chelsea Boots

Rated 3.4295 out of 5 starsRated 3.4295 out of 5 starsRated 3.4295 out of 5 starsRated 3.4295 out of 5 starsRated 3.4295 out of 5 stars(149)

AriatMen's Classic Cash Wide Square Toe Western Boots

Internet Exclusive
Rated 4.7857 out of 5 starsRated 4.7857 out of 5 starsRated 4.7857 out of 5 starsRated 4.7857 out of 5 starsRated 4.7857 out of 5 stars(28)

FryeMen's Leather 12R O-Ring Harness Hardware Square Toe Boots

Rated 4.4756 out of 5 starsRated 4.4756 out of 5 starsRated 4.4756 out of 5 starsRated 4.4756 out of 5 starsRated 4.4756 out of 5 stars(82)

UGGMen's Classic Ultra Mini Western Boots

Internet Exclusive
Extended Sizes

Steve MaddenMen's Satori Leather Split Toe Boot

Internet Exclusive

SorelMen's Cyprus Waterproof Suede 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(1)

ALIGNMen's Ryder Weatherproof Suede Boots

Internet Exclusive
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(1)

Twisted XMen's Driving CellStretch Leather Moc Toe Chukka Boots

Extended Sizes
Rated 2.0 out of 5 starsRated 2.0 out of 5 starsRated 2.0 out of 5 starsRated 2.0 out of 5 starsRated 2.0 out of 5 stars(1)

Dr. MartensMen's Lowell Chukka Boots

Internet Exclusive

Josef SeibelMen's Erroll 52 Chukka 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)

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

Internet Exclusive
Extended Sizes

AriatMen's Wexford Waterproof Chelsea Boots

Rated 4.5424 out of 5 starsRated 4.5424 out of 5 starsRated 4.5424 out of 5 starsRated 4.5424 out of 5 starsRated 4.5424 out of 5 stars(295)

SorelMen's Buxton Lite Lace Plus Waterproof Boots

Extended Sizes
Rated 4.125 out of 5 starsRated 4.125 out of 5 starsRated 4.125 out of 5 starsRated 4.125 out of 5 starsRated 4.125 out of 5 stars(8)

Cole HaanMen's Chamberlin Chukka Boots

Internet Exclusive

ALIGNMen's Rangley Suede Chelsea Boots

Internet Exclusive

Sam EdelmanMen's Cameron Suede Chukka Boots

ALIGNMen's Eddy Waterproof Leather Lace Up Boots

Internet Exclusive

Johnston & MurphyMen's Calder Suede Chelsea 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)

Johnston & MurphyCollection Men's Hartford Moc Toe Boot

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)

Johnston & MurphyMens Barrett Suede Zip Boots

Extended Sizes
Rated 1.5 out of 5 starsRated 1.5 out of 5 starsRated 1.5 out of 5 starsRated 1.5 out of 5 starsRated 1.5 out of 5 stars(2)

AriatMen's Rambler Recon Leather Square Toe Chelsea Boot

Rated 4.7692 out of 5 starsRated 4.7692 out of 5 starsRated 4.7692 out of 5 starsRated 4.7692 out of 5 starsRated 4.7692 out of 5 stars(13)

AriatMen's Sport Cool VentTEK Western Boots

Extended Sizes
Rated 4.6133 out of 5 starsRated 4.6133 out of 5 starsRated 4.6133 out of 5 starsRated 4.6133 out of 5 starsRated 4.6133 out of 5 stars(75)

Dune LondonMen's Smoky Leather Casual Ankle Boots

Internet Exclusive

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)
See all 6 colors >

DingoMen's Barnsley Leather and Suede Square Toe Zip Booties

Internet Exclusive

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

Extended Sizes

Johnston & MurphyCollection Men's Hartford Moc Toe Lace-Up Boots

Internet Exclusive

DingoMen's Rowdy Leather O-Ring Harness Snip Toe Ankle Boots

Internet Exclusive

Twisted XMen's Cellstretch® Wedge Sole 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)

DingoMen's Bulls Eye Leopard Print Suede Western Boots

Internet Exclusive

Steve MaddenMen's Hatton Suede Chelsea Boots

Internet Exclusive

Johnston & MurphyMen's Clint Leather Chelsea Boot

Internet Exclusive

Johnston & MurphyMen's Britton Suede Boots

Internet Exclusive

AriatMen's Clean Country Suede Chukka Boots

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(28)

Johnston & MurphyCollection Men's Hartford Suede Plain Toe 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)

FryeMen's Barrett Leather 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)

DingoMen's Lennox Vintage Leather Square Toe Booties

Internet Exclusive

ALIGNMen's Rangley Leather Chelsea Boots

Internet Exclusive

FryeMen's Paul Waxed Suede Chukka Boots

Internet Exclusive

FryeMen's Paul Inside Zip Boots

Internet Exclusive

Dan PostMen's Bayou 13" Caiman Square Toe Western Boots

Internet Exclusive

ALIGNMen's Rivers Weatherproof Oiled Leather Flannel Lined Winter Boots

Internet Exclusive
Twisted X Men's Chukka Hiker Waterproof BootsMen's Chukka Hiker Waterproof Boots

Twisted XMen's Chukka Hiker Waterproof Boots

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(2)
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