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  • 281 Items
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Sam Edelman Men's Cameron Suede Chukka BootsMen's Cameron Suede Chukka Boots

Sam EdelmanMen's Cameron Suede Chukka Boots

Tecovas Men's The Earl Goat Leather Roper BootsMen's The Earl Goat Leather Roper Boots

TecovasMen's The Earl Goat Leather Roper 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)
Steve Madden Men's Noby Leather BootsMen's Noby Leather Boots

Steve MaddenMen's Noby Leather Boots

Extended Sizes
Blundstone Men's Ant Brn 550 Water Resistant Antique Leather Chelsea BootsMen's Ant Brn 550 Water Resistant Antique Leather Chelsea Boots

BlundstoneMen's Ant Brn 550 Water Resistant Antique Leather Chelsea 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(14)
Cole Haan Men's Chamberlin Water Resistant Nubuck Chukka BootsMen's Chamberlin Water Resistant Nubuck Chukka Boots

Cole HaanMen's Chamberlin Water Resistant Nubuck Chukka Boots

Tecovas Men's The Cartwright Goat Leather Cowboy BootsMen's The Cartwright Goat Leather Cowboy Boots

TecovasMen's The Cartwright Goat Leather Cowboy Boots

Extended Sizes
Born Men's Nigel Leather Lace Up BootsMen's Nigel Leather Lace Up Boots

BornMen's Nigel Leather Lace Up 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(3)
Frye Tyler Flex Leather Chelsea BootsTyler Flex Leather Chelsea Boots

FryeTyler Flex Leather Chelsea Boots

Internet Exclusive
Men's Cameron Suede Chukka Boots

PLACEHOLDERMen's Cameron Suede Chukka Boots

MerrellMen's Speed Strike 2 Leather Mid Waterproof Boots

Rated 4.3235 out of 5 starsRated 4.3235 out of 5 starsRated 4.3235 out of 5 starsRated 4.3235 out of 5 starsRated 4.3235 out of 5 stars(34)

DingoMen's Bulls Eye Cow Print Calf Hair Western Boots

PLACEHOLDERMen's Cameron Suede Chukka Boots

BlundstoneMen's Water-Resistant Leather Chelsea Boots

Johnston & MurphyMens XC Flex® Cade Leather Wingtip Boots

Internet Exclusive

PLACEHOLDERMen's Cameron Suede Chukka Boots

AriatMen's Maverick Western Five Row Stitch Boots

Rated 4.7333 out of 5 starsRated 4.7333 out of 5 starsRated 4.7333 out of 5 starsRated 4.7333 out of 5 starsRated 4.7333 out of 5 stars(15)

Cole HaanMen's Windham Grand Chelsea Waterproof Boots

Internet Exclusive

PLACEHOLDERMen's Cameron Suede Chukka Boots

Steve MaddenMen's Montreux 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 & MurphyMen's XC+ Durham Waterproof Leather Cap Toe Boots

Extended Sizes
Rated 4.875 out of 5 starsRated 4.875 out of 5 starsRated 4.875 out of 5 starsRated 4.875 out of 5 starsRated 4.875 out of 5 stars(8)
See all 6 colors >

DingoMen's Workhorse Leather Snip Toe Western Boots

Internet Exclusive

TecovasMen's The Earl Goat Leather Roper Boots

BlundstoneMen's Ant Brn 550 Water Resistant Rustic Leather Chelsea Boots

Rated 4.913 out of 5 starsRated 4.913 out of 5 starsRated 4.913 out of 5 starsRated 4.913 out of 5 starsRated 4.913 out of 5 stars(23)

TecovasMen's The Knox Roper Boots

Internet Exclusive
Extended Sizes

UGGMen's Neumel Cold Weather Waterproof Hybrid 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(6)

Steve MaddenMen's Sturgis Suede Western Boots

Internet Exclusive

To Boot New YorkMen's Largo Chelsea Boots

Marc NolanMen's Dante Leather Chelsea Boots

Extended Sizes

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)

BlundstoneMen's Ant Brn 550 Water Resistant Leather Chelsea Boots

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

Internet Exclusive

TecovasMen's The Cartwright Cowhide Leather Cowboy 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)

Dune LondonMen's Matchin Leather Chelsea Boots

Johnston & MurphyMen's Clint Leather Chukka Boots

Internet Exclusive

FryeMen's Paul Chukka Lite Boots

FryeMen's Campus Leather Roper Boots

Internet Exclusive
Extended Sizes

TimberlandMen's Auburn Falls Waterproof Nubuck Chukka Boots

Internet Exclusive

Dr. MartensMen's 1460 Boots

Extended Sizes

FryeMen's Austin Oiled Suede Inside Zip Western Boots

Internet Exclusive

FryeMen's Leather 12R O-Ring Harness Hardware Square Toe 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 Sturgis 13" Python Snake Leather Western Boots

Internet Exclusive

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)

Johnston & MurphyMen's Britton Leather Boots

Internet Exclusive

Johnston & MurphyMen's Ripley Leather Zip Boots

BirkenstockMen's Highwood Chelsea Boots

Internet Exclusive

TecovasMen's The Doc Goat Leather Square Toe Cowboy Boots

Extended Sizes

TecovasMen's The Doc Frontier Western Boots

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)

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)

Marc NolanMen's Logan Cowhide Chukka Boots

Internet Exclusive
Extended Sizes

Marc NolanMen's Sawyer Cow Print Pony Hair Cowboy 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)

Steve MaddenMen's Devera Leather Chelsea Boots

Internet Exclusive

ALIGNMen's Ryder Weatherproof Leather Boots

Internet Exclusive

Cole HaanMen's Chamberlin Water Resistant Nubuck Chelsea 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)

TecovasMen's Doc Color Block Bison Leather Square Toe Cowboy Boots

Extended Sizes

DannerMen's Logger Moc 917 GTX Waterproof Nubuck Leather Boots

Internet Exclusive
Extended Sizes

Johnston & MurphyMens Barrett Suede Zip Boots

Internet Exclusive
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)

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)

AriatMen's Wexford Waterproof Chelsea Boots

Rated 4.5338 out of 5 starsRated 4.5338 out of 5 starsRated 4.5338 out of 5 starsRated 4.5338 out of 5 starsRated 4.5338 out of 5 stars(296)

Johnston & MurphyMen's Conlin Leather Side Zip Boots

Internet Exclusive

Johnston & MurphyMens XC+ Durham Wingtip Waterproof Boots

Internet Exclusive

FryeMen's Connor Leather Chelsea Boots

Steve MaddenMen's Satori Leather Split Toe Boot

Internet Exclusive

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

Internet Exclusive

AriatMen's Cooper Water Resistant Leather Chelsea Boots

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(2)

UGGMen's Classic Ultra Mini Colorblock Booties

Internet Exclusive

AriatMen's Sonoro Leather Roper Toe Western Boots

Rated 4.5455 out of 5 starsRated 4.5455 out of 5 starsRated 4.5455 out of 5 starsRated 4.5455 out of 5 starsRated 4.5455 out of 5 stars(11)

Dr. MartensMen's 2976 Chelsea Boots

Internet Exclusive
Extended Sizes
Rated 4.6364 out of 5 starsRated 4.6364 out of 5 starsRated 4.6364 out of 5 starsRated 4.6364 out of 5 starsRated 4.6364 out of 5 stars(11)

Dr. MartensMen's Lowell Chukka Boots

Internet Exclusive

Johnston & MurphyMen's XC Flex Cade Plain Toe Lug Boots

Internet Exclusive

Johnston & MurphyMens Ripley Suede Chukka Boot

Internet Exclusive

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

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

Rated 3.4238 out of 5 starsRated 3.4238 out of 5 starsRated 3.4238 out of 5 starsRated 3.4238 out of 5 starsRated 3.4238 out of 5 stars(151)

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)

Johnston & MurphyMen's Reeve Leather Chelsea Dress Boots

Extended Sizes

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)

DingoMen's Serpico Snake Embossed Leather Western Booties

Internet Exclusive

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)

Sam EdelmanMen's Elliott Suede Lace Up Boots

Internet Exclusive
Extended Sizes

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)

UGGMen's Classic Ultra Mini Weather Hybrid 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(1)

Johnston & MurphyMens Calder Suede Chukka Boot

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 Abram Western Boots

Internet Exclusive
Extended Sizes

Marc NolanMen's Sawyer Leather Cowboy Boots

Internet Exclusive
Extended Sizes

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)

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

Internet Exclusive

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)

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)

Cole HaanMen's Chamberlin Chukka Boots

Internet Exclusive

Sam EdelmanMen's Taylor Suede Lace Up Wing Tip Boots

Internet Exclusive

UGGMen's Classic Ultra Mini Western Boots

Internet Exclusive
Extended Sizes

ALIGNMen's Rangley Leather Chelsea Boots

Internet Exclusive

Johnston & MurphyMen's XC+Durham 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(3)

DingoMen's Bandit Leopard Print Suede and Leather Coin Harness Western Ankle Boots

Internet Exclusive

Dan PostMen's Sonara 11" Leather Square Toe Western Boots

Extended Sizes

Dan PostMen's Gallup 13" Leather Snip Toe Western Boots

Internet Exclusive
Extended Sizes

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 & Murphy Men's Britton Suede BootsMen's Britton Suede Boots

Johnston & MurphyMen's Britton Suede Boots

Internet Exclusive
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