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  • 213 Items
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Sam Edelman Men's Cameron Leather Cozy Chukka BootsMen's Cameron Leather Cozy Chukka Boots

Sam EdelmanMen's Cameron Leather Cozy Chukka Boots

Johnston & Murphy Men's Clint Leather Chukka BootsMen's Clint Leather Chukka Boots

Johnston & MurphyMen's Clint Leather Chukka Boots

Internet Exclusive
Johnston & Murphy Men's Britton Leather BootsMen's Britton Leather Boots

Johnston & MurphyMen's Britton Leather Boots

Internet Exclusive
Johnston & Murphy Mens XC Flex® Cade Leather Wingtip BootsMens XC Flex® Cade Leather Wingtip Boots

Johnston & MurphyMens XC Flex® Cade Leather Wingtip Boots

Internet Exclusive
Johnston & Murphy Mens Calder Suede Chukka BootMens Calder Suede Chukka Boot

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)
Frye Men's Hudson Leather Wedge Work BootsMen's Hudson Leather Wedge Work Boots

FryeMen's Hudson Leather Wedge Work 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(3)
Dune London Men's Matchin Leather Chelsea BootsMen's Matchin Leather Chelsea Boots

Dune LondonMen's Matchin Leather Chelsea Boots

Steve Madden Men's Highline Leather Chelsea BootsMen's Highline Leather Chelsea Boots

Steve MaddenMen's Highline Leather Chelsea Boots

Internet Exclusive
Extended Sizes
Men's Cameron Leather Cozy Chukka Boots

PLACEHOLDERMen's Cameron Leather Cozy Chukka 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)

To Boot New YorkMen's Largo Chelsea Boots

PLACEHOLDERMen's Cameron Leather Cozy Chukka Boots

Steve MaddenMen's Meeker Leather Chukka Boots

Internet Exclusive

BirkenstockMen's Highwood Chelsea Boots

Internet Exclusive

PLACEHOLDERMen's Cameron Leather Cozy Chukka Boots

Johnston & MurphyMen's Ripley Oiled Leather Inside Zip Boots

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)

PLACEHOLDERMen's Cameron Leather Cozy Chukka Boots

Steve MaddenMen's Satori Leather Split Toe Boot

Internet Exclusive

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

Internet Exclusive

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)

MerrellMen's Moab 3 Mid Waterproof Hiking Boots

Extended Sizes
Rated 4.4094 out of 5 starsRated 4.4094 out of 5 starsRated 4.4094 out of 5 starsRated 4.4094 out of 5 starsRated 4.4094 out of 5 stars(889)

Steve MaddenMen's Sturgis Suede Western Boots

Internet Exclusive

Johnston & MurphyMen's Reeve Leather Chelsea Dress Boots

Extended Sizes

Steve MaddenMen's Devera Leather Chelsea Boots

Internet Exclusive

Josef SeibelMen's Erroll 52 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(1)

Cole HaanMen's Chamberlin Chukka 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)

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 & 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)

PikolinosMen's Vigo Leather Lace Up Zip Ankle Boots

Internet Exclusive

AriatMen's Renegade Leather Narrow Cutter Toe Cowboy Boots

Internet Exclusive
Rated 4.8846 out of 5 starsRated 4.8846 out of 5 starsRated 4.8846 out of 5 starsRated 4.8846 out of 5 starsRated 4.8846 out of 5 stars(52)

Cole HaanMen's Chamberlin Water Resistant Nubuck Chelsea 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)

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)

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

Internet Exclusive

AriatMen's Spitfire Boots

Extended Sizes
Rated 4.7588 out of 5 starsRated 4.7588 out of 5 starsRated 4.7588 out of 5 starsRated 4.7588 out of 5 starsRated 4.7588 out of 5 stars(369)

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)

Johnston & MurphyMen's Ripley Leather Zip Boots

Johnston & MurphyMens Ripley Suede Chukka Boot

Internet Exclusive

FryeMen's Landon Leather Midlace Cap 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(2)

Bed StuMen's Michelangelo Rustic Leather Chelsea Boots

Internet Exclusive

FryeMen's Paul Leather Cap Toe Lace Up Boots

Internet Exclusive
Rated 4.25 out of 5 starsRated 4.25 out of 5 starsRated 4.25 out of 5 starsRated 4.25 out of 5 starsRated 4.25 out of 5 stars(4)

Tony LamaMen's Houston Leather Western Chelsea Boots

Internet Exclusive

Johnston & MurphyMen's Britton Suede Boots

Internet Exclusive

FryeMen's Connor 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(5)

SperryMen's Drake 1-Eye Waterproof Boots

Internet Exclusive
Extended Sizes

UGGMen's Classic Ultra Mini Western Boots

Internet Exclusive
Extended Sizes

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)

Marc NolanMen's Logan Cowhide Chukka Boots

Internet Exclusive
Extended Sizes

Steve MaddenMen's Hatton Suede Chelsea Boots

Internet Exclusive

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 Bandit Suede and Leather Coin Harness Western Ankle 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)

BornMen's Rex Distressed Suede Leather Boots

Internet Exclusive

Johnston & MurphyMen's Clint Suede Slip On Chelsea Boot

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)

FryeMen's Paul Inside Zip Boots

Internet Exclusive

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)

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)

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

Internet Exclusive

Steve MaddenMen's Avenue Suede Chelsea Boots

Internet Exclusive

Bed StuMen's Illiad Leather Chukka Boots

Internet Exclusive

Justin BootsMen's Crazy Buck Leather Western Chelsea Booties

Internet Exclusive
Extended Sizes

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

Internet Exclusive

Johnston & MurphyMen's Clint Leather Chelsea Boot

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)

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)

Sam EdelmanMen's Taylor Suede Lace Up Wing Tip Boots

Internet Exclusive

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)

ALIGNMen's Rangley Leather Chelsea Boots

Internet Exclusive

Sam EdelmanMen's Cameron Suede Chukka Boots

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

Internet Exclusive

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)

DannerMen's Bull Run Leather 6" Chelsea Boots

Extended Sizes

AriatMen's Easton Leather R Toe Western Boots

Rated 4.8182 out of 5 starsRated 4.8182 out of 5 starsRated 4.8182 out of 5 starsRated 4.8182 out of 5 starsRated 4.8182 out of 5 stars(11)

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

FryeMen's Austin Leather Western Boots

Internet Exclusive
Rated 2.75 out of 5 starsRated 2.75 out of 5 starsRated 2.75 out of 5 starsRated 2.75 out of 5 starsRated 2.75 out of 5 stars(8)

AriatMen's Hustler Leather Narrow Cutter Toe Cowboy Boots

Internet Exclusive
Rated 4.8475 out of 5 starsRated 4.8475 out of 5 starsRated 4.8475 out of 5 starsRated 4.8475 out of 5 starsRated 4.8475 out of 5 stars(59)

ALIGNMen's Ryder Weatherproof Leather Boots

Internet Exclusive

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)

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)

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

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

FryeMen's Campus Suede Boots

Internet Exclusive

ALIGNMen's Rivers Weatherproof Oiled Leather Flannel Lined Winter Boots

Internet Exclusive

FryeMen's Connor Suede Chelsea Boots

Internet Exclusive

ALIGNMen's Rangley Suede Chelsea Boots

Internet Exclusive

Sam EdelmanMen's Cameron Suede Chukka Boots

Internet Exclusive

Dune LondonMen's Smoky Leather Casual Ankle Boots

Internet Exclusive

Steve MaddenMen's Garno Suede Lug Sole Hiker Boots

Internet Exclusive
Only size 9 available

FryeMen's Austin Inside Zip Western Boots

Internet Exclusive

Sam EdelmanMen's Cameron Suede Cozy Chukka Boots

Internet Exclusive

SorelMen's Ambler Fireside Waterproof Chukka Boots

Internet Exclusive
Extended Sizes

Twisted XMen's Chelsea Driving Moc Boots

Sam EdelmanMen's Cade Suede Chelsea Boots

Internet Exclusive

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)
Frye Men's Barrett Leather Lace Up BootsMen's Barrett Leather Lace Up Boots

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)
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