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  • 98 Items
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Polo Ralph Lauren Men's Ranger Tumbled Leather Buckle Lug Sole BootsMen's Ranger Tumbled Leather Buckle Lug Sole Boots

Polo Ralph LaurenMen's Ranger Tumbled Leather Buckle Lug Sole Boots

Extended Sizes
Rated 4.5962 out of 5 starsRated 4.5962 out of 5 starsRated 4.5962 out of 5 starsRated 4.5962 out of 5 starsRated 4.5962 out of 5 stars(52)
Steve Madden Men's Harken Leather Chukka BootsMen's Harken Leather Chukka Boots

Steve MaddenMen's Harken Leather Chukka Boots

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

Johnston & MurphyMens Calder Suede Chukka Boot

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)
Born Men's Henry Chukka BootsMen's Henry Chukka Boots

BornMen's Henry Chukka Boots

UGG Men's Neumel Classic Fur Lined Suede Lace Up Chukka BootsMen's Neumel Classic Fur Lined Suede Lace Up Chukka Boots

UGGMen's Neumel Classic Fur Lined Suede Lace Up Chukka Boots

Extended Sizes
Rated 4.8753 out of 5 starsRated 4.8753 out of 5 starsRated 4.8753 out of 5 starsRated 4.8753 out of 5 starsRated 4.8753 out of 5 stars(369)
Johnston & Murphy Men's XC Flex Cade Plain Toe Lug BootsMen's XC Flex Cade Plain Toe Lug Boots

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

Internet Exclusive
Sorel Men's Lark 47 Moc Toe Waterproof BootsMen's Lark 47 Moc Toe Waterproof Boots

SorelMen's Lark 47 Moc Toe Waterproof Boots

Extended Sizes
Twisted X Men's Driving Leather Moc Toe Chukka BootsMen's Driving Leather Moc Toe Chukka Boots

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)
Men's Ranger Tumbled Leather Buckle Lug Sole Boots

PLACEHOLDERMen's Ranger Tumbled Leather Buckle Lug Sole Boots

Extended Sizes
Rated 4.5962 out of 5 starsRated 4.5962 out of 5 starsRated 4.5962 out of 5 starsRated 4.5962 out of 5 starsRated 4.5962 out of 5 stars(52)

Johnston & MurphyMen's Clint Leather Chukka Boots

Marc NolanMen's Del Mar Pebble Leather Contrast Trim Penny Loafer Mules

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)

PLACEHOLDERMen's Ranger Tumbled Leather Buckle Lug Sole Boots

Extended Sizes
Rated 4.5962 out of 5 starsRated 4.5962 out of 5 starsRated 4.5962 out of 5 starsRated 4.5962 out of 5 starsRated 4.5962 out of 5 stars(52)

Steve MaddenMen's Ebner Leather Cap Toe Boots

TimberlandMen's Auburn Falls Waterproof Nubuck Chukka Boots

PLACEHOLDERMen's Ranger Tumbled Leather Buckle Lug Sole Boots

Extended Sizes
Rated 4.5962 out of 5 starsRated 4.5962 out of 5 starsRated 4.5962 out of 5 starsRated 4.5962 out of 5 starsRated 4.5962 out of 5 stars(52)

UGGMen's Idyllwild Leather Lace 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)

Polo Ralph LaurenMen's Ranger Work Boots

Internet Exclusive

PLACEHOLDERMen's Ranger Tumbled Leather Buckle Lug Sole Boots

Extended Sizes
Rated 4.5962 out of 5 starsRated 4.5962 out of 5 starsRated 4.5962 out of 5 starsRated 4.5962 out of 5 starsRated 4.5962 out of 5 stars(52)

Johnston & MurphyMens XC+ Durham Wingtip Waterproof Boots

Internet Exclusive

Johnston & MurphyMens XC Flex® Cade Leather Wingtip 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 Grand Neoclassic FlexCraft Chukka Boots

Internet Exclusive

Johnston & MurphyMen's Calder Leather Chukka Lace Up Boots

Extended Sizes
Rated 4.2 out of 5 starsRated 4.2 out of 5 starsRated 4.2 out of 5 starsRated 4.2 out of 5 starsRated 4.2 out of 5 stars(65)

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)

Twisted XMen's Work Steel Toe Leather 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)

AriatMen's Silversmith Suede Square Toe Slippers

Extended Sizes
Rated 4.795 out of 5 starsRated 4.795 out of 5 starsRated 4.795 out of 5 starsRated 4.795 out of 5 starsRated 4.795 out of 5 stars(200)

TimberlandMen's Waterproof Field Boots

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(8)

Marc NolanMen's Del Mar Cow Print Dark Horse Penny Loafer Mules

Internet Exclusive
Extended Sizes

Marc NolanMen's Hampton Suede Kiltie Tassel Mules

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)

Twisted XMen's Work Composite Toe Slip On Driving Moccasins

Internet Exclusive
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(1)

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)

AriatMen's Spitfire Boots

Extended Sizes
Rated 4.7493 out of 5 starsRated 4.7493 out of 5 starsRated 4.7493 out of 5 starsRated 4.7493 out of 5 starsRated 4.7493 out of 5 stars(371)

Twisted XMen's Chukka Driving Mocs

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)

Twisted XMen's Driving Leather Moccasin 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(9)

L.L.BeanMen's Stonington Leather Moc Toe Boots

Extended Sizes
Rated 4.6175 out of 5 starsRated 4.6175 out of 5 starsRated 4.6175 out of 5 starsRated 4.6175 out of 5 starsRated 4.6175 out of 5 stars(481)

BornMen's Nigel Leather Lace Up 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)

Johnston & MurphyMen's XC+ Durham Waterproof Leather Cap Toe Boots

Extended Sizes
Rated 4.7778 out of 5 starsRated 4.7778 out of 5 starsRated 4.7778 out of 5 starsRated 4.7778 out of 5 starsRated 4.7778 out of 5 stars(9)

Steve MaddenMen's Noby Leather Boots

Extended Sizes

Sam EdelmanMen's Cameron Suede Chukka Boots

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)

Flag LTD.Flag Ltd. Men's Garrett Leather Chukka Boots

Dillard's Exclusive

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)

COACHMen's Signature Jaquard Sport Mules

Extended Sizes

UGGMen's Loften Waterproof Lace Up Shoes

Extended Sizes

AriatMen's Clean Country Suede Chukka Boots

Rated 4.4333 out of 5 starsRated 4.4333 out of 5 starsRated 4.4333 out of 5 starsRated 4.4333 out of 5 starsRated 4.4333 out of 5 stars(30)

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 Chamberlin Grand Water Resistant Chukka Boots

BirkenstockMen's Uppsala Mid Suede Boots

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(3)

COACHMen's Sport Mules

Internet Exclusive
Extended Sizes
Rated 4.7391 out of 5 starsRated 4.7391 out of 5 starsRated 4.7391 out of 5 starsRated 4.7391 out of 5 starsRated 4.7391 out of 5 stars(23)

Cole HaanMen's Chamberlin Water Resistant Nubuck Chukka Boots

BornMen's Rex Boots

Internet Exclusive
Extended Sizes

AriatMen's Square Toe Silversmith Slippers

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(205)

Marc NolanMen's Shiloh Cow Print Buckle Hardware Clog

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

Internet Exclusive

Steve MaddenMen's Albie Suede Chukka Boots

Twisted XMen's Chukka Driving Mocs

Internet Exclusive
Extended Sizes

DannerMen's Logger Moc 917 GTX Waterproof Nubuck Leather Boots

Internet Exclusive
Extended Sizes

Steve MaddenMen's Meeker Leather Chukka Boots

Internet Exclusive

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)

Twisted XMen's Driving Moccasin Chukka Boots

Internet Exclusive
Extended Sizes

Bed StuMen's Illiad Leather Chukka Boots

Marc NolanMen's Hampton Croco Embossed Leather Tassel Mules

Internet Exclusive

Cole HaanMen's Chamberlin Chukka Boots

Internet Exclusive

AriatMen's Split Rock Leather Moc Toe Chukka Boots

Rated 4.9375 out of 5 starsRated 4.9375 out of 5 starsRated 4.9375 out of 5 starsRated 4.9375 out of 5 starsRated 4.9375 out of 5 stars(16)

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)

AriatMen's Spitfire Waterproof Leather Boots

Extended Sizes
Rated 4.5147 out of 5 starsRated 4.5147 out of 5 starsRated 4.5147 out of 5 starsRated 4.5147 out of 5 starsRated 4.5147 out of 5 stars(68)

Johnston & MurphyMen's Britton Leather Boots

Internet Exclusive

Twisted XMen's Chukka Driving Mocs

Internet Exclusive
Extended Sizes

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)

Dune LondonMen's Smoky Leather Casual Ankle Boots

Internet Exclusive
Only size 7 available

Twisted XMen's Chukka Driving CellStretch Mocs

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)

Marc NolanMen's Del Mar Croco Embossed Suede Penny Loafer Mules

Internet Exclusive
Extended Sizes

Dr. MartensMen's Lowell Chukka Boots

Internet Exclusive

FryeMen's Paul Leather Chukka Boots

Internet Exclusive

Marc NolanMen's Bahia Raffia Mule

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(1)

Marc NolanMen's Logan Cowhide Chukka Boots

Internet Exclusive
Extended Sizes

Marc NolanMen's Logan Chukka Boots

Internet Exclusive
Extended Sizes

Johnston & MurphyMens Ripley Suede Chukka Boot

Internet Exclusive

BornMen's Rex Distressed Suede Leather Boots

Internet Exclusive

Sam EdelmanMen's Cameron Leather Cozy Chukka Boots

Twisted XMen's Chukka Driving Mocs

Internet Exclusive
Extended Sizes

Johnston & MurphyMen's Britton Suede 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)

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(1)

AriatMen's Rancher Suede Square Toe Slippers

Extended Sizes

ECCOMen's Metropole Prague Chukka Boots

Internet Exclusive

SorelMen's Ambler Fireside Waterproof Chukka Boots

Internet Exclusive
Extended Sizes

ECCOMen's Metropole Milan Suede Chukka Boots

SorelMen's Outing NW Mid Waterproof Boots

Extended Sizes

ALIGNMen's Rivers Water Resistant Oiled Leather Flannel Lined Winter Boots

Internet Exclusive

OOFOSMen's OOcoozie Thermo Mules

Internet Exclusive
Only size 9.5 available

Sam EdelmanMen's Cameron Suede Cozy Chukka Boots

Internet Exclusive

ALIGNAlign Men's William Water Resistant Leather Boots

Internet Exclusive

BornMen's Harrison Leather Chukka Boots

Internet Exclusive
Extended Sizes
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(34)

Twisted XMen's ECO Moc-Toe Lace Up Boot

Only size 8, 10.5 available
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 Moc Toe 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(3)

Johnston & MurphyMen's Upton Leather Chukka Boots

Permanently Reduced
Orig.
Now
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)

BornMen's Ethan Distressed Suede Boots

Permanently Reduced
Orig.
Now
Extended Sizes

Marc NolanMen's Del Mar Pebble Leather Penny Loafer Mules

Limited Time Offer
Orig.
Now
Internet Exclusive
Extended Sizes

Cole HaanMen's Morse Leather Chukka Boots

Permanently Reduced
Orig.
Now
Internet Exclusive
Johnston & Murphy Men's XC+Parker Waterproof Leather Chukka BootsMen's XC+Parker Waterproof Leather Chukka Boots

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

Permanently Reduced
Orig.
Now
Internet Exclusive
Extended Sizes
Only size 9.5 available
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)
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