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  • 208 Items
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Ariat Men's Lookout Leather Chukka BootsMen's Lookout Leather Chukka Boots

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)
Cole Haan Men's Morse Leather Chukka BootsMen's Morse Leather Chukka Boots

Cole HaanMen's Morse Leather Chukka Boots

Marc Nolan Men's Aiden Croco Embossed Leather BootsMen's Aiden Croco Embossed Leather Boots

Marc NolanMen's Aiden Croco Embossed Leather Boots

Extended Sizes
Twisted X Men's Cellstretch® Wedge Sole BootsMen's Cellstretch® Wedge Sole Boots

Twisted XMen's Cellstretch® Wedge Sole Boots

Extended Sizes
Merrell Men's Tempo Sol Waterproof Multi BootsMen's Tempo Sol Waterproof Multi Boots

MerrellMen's Tempo Sol Waterproof Multi 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(10)
Merrell Men's Moab 3 Mid Waterproof Hiking BootsMen's Moab 3 Mid Waterproof Hiking Boots

MerrellMen's Moab 3 Mid Waterproof Hiking Boots

Extended Sizes
Rated 4.3493 out of 5 starsRated 4.3493 out of 5 starsRated 4.3493 out of 5 starsRated 4.3493 out of 5 starsRated 4.3493 out of 5 stars(418)
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

Internet Exclusive
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
Men's Lookout Leather Chukka Boots

PLACEHOLDERMen'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)

TimberlandMen's Redwood Falls Waterproof Leather Chukka Boots

Extended Sizes
Rated 4.3448 out of 5 starsRated 4.3448 out of 5 starsRated 4.3448 out of 5 starsRated 4.3448 out of 5 starsRated 4.3448 out of 5 stars(58)

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)

PLACEHOLDERMen'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)

L.L.BeanMen's Eco Bay Nubuck Chukka Boots

Polo Ralph LaurenMen's Alpine Leather Lite Boots

PLACEHOLDERMen'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)

Polo Ralph LaurenMen's Ranger Suede Patch Detail 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 Water Resistant Nubuck Cap Toe Boots

Internet Exclusive

PLACEHOLDERMen'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)

Johnston & MurphyMen's Upton Leather Chukka Boots

Extended Sizes

Marc NolanMen's Belmont Appaloosa Cow Print Brogue Wingtip Combat Boots

Extended Sizes

SorelMen's Daystorm Horizon GTX Waterproof Boots

Internet Exclusive
Extended Sizes

TaftMen's Rome Floral Embossed Leather Cap Toe Boots

Internet Exclusive
Extended Sizes
Rated 4.4804 out of 5 starsRated 4.4804 out of 5 starsRated 4.4804 out of 5 starsRated 4.4804 out of 5 starsRated 4.4804 out of 5 stars(102)

ECCOMen's MX GTX Mid Waterproof Reflective Tab Lace Up Sneaker Boots

Internet Exclusive
Extended Sizes
Only size 41(7/7.5) available
Rated 4.1667 out of 5 starsRated 4.1667 out of 5 starsRated 4.1667 out of 5 starsRated 4.1667 out of 5 starsRated 4.1667 out of 5 stars(6)

SorelMen's Slabtown 62 Caribou Leather Waterproof Boots

Internet Exclusive
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(2)

Cole HaanMen's Chamberlin Water Resistant Suede Cap Toe Boots

Internet Exclusive

Twisted XMen's ECO Moc-Toe Lace Up Boot

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 & MurphyMens XC+ Durham Embossed Leather Brogue Detail Wingtip Shearling Waterproof Boots

Internet Exclusive
Extended Sizes

BornMen's Nigel Suede 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)

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)

SorelMen's Madson II Moc Toe Waterproof Boots

Internet Exclusive
Rated 4.6154 out of 5 starsRated 4.6154 out of 5 starsRated 4.6154 out of 5 starsRated 4.6154 out of 5 starsRated 4.6154 out of 5 stars(13)

SorelMen's Buxton Lite Lace Plus Waterproof 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(7)

Kurt Geiger LondonMen's Chiltern Leather Boots

TaftMen's Rome Floral Embossed Genuine Leather Cap Toe Boots

Internet Exclusive
Extended Sizes

Bed StuMen's Protege Distressed Leather Back Zip Combat Boots

Internet Exclusive
Extended Sizes

PikolinosMen's Vigo Leather Lace Up Zip Ankle Boots

Internet Exclusive

TaftMen's Jack Paisley Jacquard Cap Toe Dress Boots

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 Hudson Leather Lug Work Boots

Rated 4.2222 out of 5 starsRated 4.2222 out of 5 starsRated 4.2222 out of 5 starsRated 4.2222 out of 5 starsRated 4.2222 out of 5 stars(9)

ALIGNMen's Ryder Weatherproof Leather Boots

Cole HaanMen's Muir Waterproof Suede Moc Toe Boots

Internet Exclusive

BelvedereMen's Alvaro Hand Painted Multi Color Ostrich Chukka Boots

Internet Exclusive

BornMen's Erik Leather Boots

Extended Sizes

TaftMen's Rome Leather Cap Toe 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)

BelvedereMen's Greco Colorblock Boots

Internet Exclusive

COACHMen's Connor Signature Logo Coated Canvas and Leather Lace Up Boots

Internet Exclusive

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)

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)

FryeMen's Hudson Leather Plain Toe Work Boots

Internet Exclusive

Twisted XMen's Driving Moccasin Chukka Boots

Internet Exclusive
Extended Sizes

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

Internet Exclusive

Bed StuMen's Lincoln Lace Up Leather Boots

Cole HaanMen's Muir Leather Moc Toe Boots

Internet Exclusive

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(2)

ALIGNMen's Ryder Weatherproof Suede Boots

Internet Exclusive

Chippewa Est. 1901Men's Serious Plus 6" Waterproof Work Boots

Internet Exclusive
Extended Sizes

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)

TaftMen's Paris Boots

Internet Exclusive
Extended Sizes
Rated 4.6713 out of 5 starsRated 4.6713 out of 5 starsRated 4.6713 out of 5 starsRated 4.6713 out of 5 starsRated 4.6713 out of 5 stars(286)

ObozMen's Bridger 8" Waterproof Leather Insulated Boots

Extended Sizes

Bed StuMen's Illiad Leather Chukka Boots

ObozMen's Katabatic Light Mid GTX Hiking Boots

Dune LondonMen's Smoky Leather Casual Ankle Boots

Internet Exclusive

Johnston & MurphyCollection Men's Hartford Suede Plain Toe Boots

Internet Exclusive

To Boot New YorkMen's Vista Chukka Boots

Internet Exclusive
Extended Sizes

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)

Twisted XMen's Work 4" Steel Toe Leather Wedge Sole Boot

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)

Ted Baker LondonMen's Blackburn Leather Brogue Wingtip Boots

Extended Sizes

ALDOMen's Farrell Leather Lace Up Boots

Internet Exclusive
Extended Sizes

MerrellMen's Moab 3 Vista Mid Waterproof Mid Hikers

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(21)

TaftMen's Jack Exotic Bird Jacquard Calfskin Dress Boots

Internet Exclusive
Extended Sizes
Rated 4.8733 out of 5 starsRated 4.8733 out of 5 starsRated 4.8733 out of 5 starsRated 4.8733 out of 5 starsRated 4.8733 out of 5 stars(150)

TaftMen's Jack Wool Calfskin Cap Toe Braided Welt Detail 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(7)

Chippewa Est. 1901Men's Edge Walker Waterproof Lace-Up Work Boots

Internet Exclusive

FryeMen's Barrett Leather Lace Up Boots

Internet Exclusive

FryeMen's Landon Leather Midlace Cap 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)

TaftMen's Saint Woven Leather Brogue Wingtip Boots

Internet Exclusive
Only size 7 available
Rated 4.8728 out of 5 starsRated 4.8728 out of 5 starsRated 4.8728 out of 5 starsRated 4.8728 out of 5 starsRated 4.8728 out of 5 stars(519)

Chippewa Est. 1901Men's Edge Walker Steel Toe Lace-Up Wedge Work Boots

Extended Sizes

TaftMen's Jack Floral Print Cotton Jacquard Calfskin Cap Toe Dress Boots

Internet Exclusive
Extended Sizes
Rated 4.8373 out of 5 starsRated 4.8373 out of 5 starsRated 4.8373 out of 5 starsRated 4.8373 out of 5 starsRated 4.8373 out of 5 stars(1309)

ALDOMen's Walton Leather Lace Up Booties

Internet Exclusive
Extended Sizes

TaftMen's Jack Floral Jacquard Cap Toe Dress 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)

ALIGNMen's Rivers Weatherproof Oiled Leather Boots

Internet Exclusive

Chippewa Est. 1901Men's Paladin 8" Waterproof Logger 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(1)

Chippewa Est. 1901Men's Baldor 8" Steel Toe Logger 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)

TaftMen's Rome Bottega Suede Cap Toe Boots

Internet Exclusive

CarolinaMen's Elm 8" Steel Toe Logger 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(1)

CarolinaMen's Bruno Lo 6" Waterproof Work Boots

Internet Exclusive
Extended Sizes

CarolinaMen's Foreman 6" Internal MetGuard 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(2)

CarolinaMen's Forman 6" Waterproof Steel Toe Work 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(6)

Chippewa Est. 1901Men's Paladin 8" Waterproof Steel Toe Logger Work Boots

Internet Exclusive
Extended Sizes

Twisted XMen's Moc Toe Leather Lace Up 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(3)

EastlandMen's Ethan 1955 Leather Boots

Internet Exclusive
Extended Sizes
Only size 9, 12 available

CarolinaMen's Spruce Waterproof Leather Kiltie Steel Toe Logger 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(1)

CarolinaMen's Circuit 6" Waterproof Composite Toe Work Boots

Extended Sizes
Rated 3.5 out of 5 starsRated 3.5 out of 5 starsRated 3.5 out of 5 starsRated 3.5 out of 5 starsRated 3.5 out of 5 stars(4)

CarolinaMen's Birch 8" Leather Kiltie Logger Work Boots

Internet Exclusive
Extended Sizes

CarolinaMen's Elm 8" Waterproof Steel Toe Logger Work Boots

Internet Exclusive
Extended Sizes

KeenMen's Targhee III Mid Waterproof Boots

Internet Exclusive
Extended Sizes
Rated 4.1733 out of 5 starsRated 4.1733 out of 5 starsRated 4.1733 out of 5 starsRated 4.1733 out of 5 starsRated 4.1733 out of 5 stars(75)

CarolinaMen's Elm 8" Logger 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(2)

EastlandMen's Jack Chukka Boots

Internet Exclusive
Only size 10 available

CarolinaMen's 28 Series Waterproof Leather Kiltie Composite Toe 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(2)

Chippewa Est. 1901Men's Valdor 8" Waterproof Composite Toe Logger Boots

Internet Exclusive

CarolinaMen's Birch Composite Toe Logger Work Boots

Internet Exclusive
Extended Sizes
Carolina Men's Elm 8#double; Waterproof Logger Work BootsMen's Elm 8#double; Waterproof Logger Work Boots

CarolinaMen's Elm 8" Waterproof Logger Work Boots

Internet Exclusive
Extended Sizes
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