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  • 168 Items
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Timberland Men's Newmarket Chukka Leather BootsMen's Newmarket Chukka Leather Boots

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)
Twisted X Men's Driving Woven Leather Moccasin Chukka BootsMen's Driving Woven Leather Moccasin Chukka Boots

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 X Men's Work 4" Steel Toe Leather Wedge Sole BootMen's Work 4" Steel Toe Leather Wedge Sole Boot

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

Extended Sizes
Rated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 stars(2)
Chippewa Est. 1901 Men's Edge Walker Waterproof Lace-Up Work BootsMen's Edge Walker Waterproof Lace-Up Work Boots

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

Internet Exclusive
Ted Baker London Men's Blackburn Leather Brogue Wingtip BootsMen's Blackburn Leather Brogue Wingtip Boots

Ted Baker LondonMen's Blackburn Leather Brogue Wingtip Boots

Extended Sizes
Twisted X Men's Chukka Driving MoccasinsMen's Chukka Driving Moccasins

Twisted XMen's Chukka Driving Moccasins

Internet Exclusive
Extended Sizes
Rated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 stars(1)
Chippewa Est. 1901 Men's Sador 6" Waterproof Composite Toe Work BootsMen's Sador 6" Waterproof Composite Toe Work Boots

Chippewa Est. 1901Men's Sador 6" Waterproof Composite Toe Work Boots

Internet Exclusive
Rated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 stars(1)
Danner Men's Mountain 600 4.5" Leather Hiking BootsMen's Mountain 600 4.5" Leather Hiking Boots

DannerMen's Mountain 600 4.5" Leather Hiking Boots

Internet Exclusive
Extended Sizes
Men's Newmarket Chukka Leather Boots

PLACEHOLDERMen'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)

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

Internet Exclusive
Extended Sizes
Rated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 stars(1)

TaftMen's Jack Floral Jacquard Cap Toe Dress Boots

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

PLACEHOLDERMen'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)

ALIGNMen's Rivers Weatherproof Oiled Leather Flannel Lined Winter Boots

Internet Exclusive

Chippewa Est. 1901Men's Graeme 6" Waterproof Composite Toe Work Hiking Boots

Internet Exclusive
Extended Sizes
Rated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 stars(2)

PLACEHOLDERMen'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)

TaftMen's Jack Wool Calfskin Cap Toe Braided Welt Detail Boots

Internet Exclusive
Extended Sizes
Rated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 stars(7)

ALDOMen's Walton Leather Lace Up Booties

Internet Exclusive
Extended Sizes

PLACEHOLDERMen'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)

Dune LondonMen's Smoky Leather Casual Ankle Boots

Internet Exclusive

TaftMen's Rome Bottega Suede Cap Toe Boots

Internet Exclusive

FryeMen's Barrett Leather Lace Up Boots

Internet Exclusive
Rated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 stars(1)

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

Internet Exclusive
Extended Sizes

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)

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

Internet Exclusive
Extended Sizes
Rated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 stars(1)

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

Extended Sizes

CarolinaMen's Elm 8" Waterproof Logger Work Boots

Internet Exclusive
Extended Sizes

CarolinaMen's Elm 8" Steel Toe Logger Work Boots

Internet Exclusive
Extended Sizes
Rated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 stars(1)

CarolinaMen's Bruno Lo 6" Waterproof Work Boots

Internet Exclusive
Extended Sizes

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)

CarolinaMen's Spruce Waterproof Leather Kiltie Steel Toe Logger Work Boots

Internet Exclusive
Extended Sizes
Rated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 stars(1)

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)

Dr. MartensMen's Combs Fold-Down Boots

Extended Sizes
Only size 11, 13 available
Rated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 stars(8)

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 28 Series 8" Waterproof Leather Kiltie Work Boots

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

CarolinaMen's Foreman 6" Internal MetGuard Work Boots

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

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

Internet Exclusive
Extended Sizes

CarolinaMen's Elm 8" Logger Work Boots

Internet Exclusive
Extended Sizes
Rated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 stars(2)

CarolinaMen's Birch 8" Leather Kiltie Logger Work Boots

Internet Exclusive
Extended Sizes

CarolinaMen's Bruno Lo Waterproof Composite Toe Work Boots

Extended Sizes

BornMen's Harrison Leather Chukka Boots

Internet Exclusive
Extended Sizes
Rated 4.697 out of 5 starsRated 4.697 out of 5 starsRated 4.697 out of 5 starsRated 4.697 out of 5 starsRated 4.697 out of 5 stars(33)

CarolinaMen's Spruce 8" Waterproof Leather Kiltie Detail Logger Work Boots

Internet Exclusive
Extended Sizes
Rated 2.5 out of 5 starsRated 2.5 out of 5 starsRated 2.5 out of 5 starsRated 2.5 out of 5 starsRated 2.5 out of 5 stars(2)

Polo Ralph LaurenMen's Ranger Suede and Twill Patch Detail Boots

Permanently Reduced
Orig.
Now
Extended Sizes
Rated 2.6 out of 5 starsRated 2.6 out of 5 starsRated 2.6 out of 5 starsRated 2.6 out of 5 starsRated 2.6 out of 5 stars(5)

MerrellMen's Moab 3 Mid Waterproof Hiking Boots

Permanently Reduced
Orig.
Now
Extended Sizes
Rated 4.3543 out of 5 starsRated 4.3543 out of 5 starsRated 4.3543 out of 5 starsRated 4.3543 out of 5 starsRated 4.3543 out of 5 stars(429)

UGGMen's Chukka Lug Suede Boots

Permanently Reduced
Orig.
Now
Extended Sizes

Polo Ralph LaurenMen's Ranger Work Boots

Permanently Reduced
Orig.
Now
Internet Exclusive
Extended Sizes
Rated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 stars(8)

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

Permanently Reduced
Orig.
Now
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)

Cole HaanMen's Muir Waterproof Suede Moc Toe Boots

Permanently Reduced
Orig.
Now
Internet Exclusive

UGGMen's Lug Chukka Boots

Permanently Reduced
Orig.
Now
Extended Sizes
Rated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 stars(1)

Flag LTD.Men's Garrett Leather Plain Toe Boots

Permanently Reduced
Orig.
Now
Dillard's Exclusive
Rated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 stars(1)

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

Permanently Reduced
Orig.
Now
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)

BornMen's Brock Distressed Suede Boots

Permanently Reduced
Orig.
Now
Extended Sizes
Rated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 stars(9)

Cole HaanMen's Chamberlin Water Resistant Suede Cap Toe Boots

Permanently Reduced
Orig.
Now
Internet Exclusive

Steve MaddenMen's Tabriz Lace Up Leather Chukka Boots

Permanently Reduced
Orig.
Now
Extended Sizes

Johnston & MurphyMen's Barret Leather Plain Toe Boots

Permanently Reduced
Orig.
Now
Extended Sizes
Rated 4 out of 5 starsRated 4 out of 5 starsRated 4 out of 5 starsRated 4 out of 5 starsRated 4 out of 5 stars(6)

Polo Ralph LaurenMen's Ranger Suede and Plaid Wool Boots

Permanently Reduced
Orig.
Now
Internet Exclusive
Extended Sizes
Only size 10, 11 available
Rated 2.3333 out of 5 starsRated 2.3333 out of 5 starsRated 2.3333 out of 5 starsRated 2.3333 out of 5 starsRated 2.3333 out of 5 stars(3)

Johnston & MurphyMen's Braxton Oiled Leather Chukka Boots

Permanently Reduced
Orig.
Now
Extended Sizes
Rated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 stars(1)

Johnston & MurphyMen's Upton Leather Chukka Boots

Permanently Reduced
Orig.
Now
Extended Sizes

Polo Ralph LaurenMen's Ranger Suede Patch Detail Boots

Permanently Reduced
Orig.
Now
Internet Exclusive
Rated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 stars(1)

Johnston & MurphyMen's Connelly Leather Plain Toe Brogue Detail Boots

Permanently Reduced
Orig.
Now
Extended Sizes
Rated 4.5833 out of 5 starsRated 4.5833 out of 5 starsRated 4.5833 out of 5 starsRated 4.5833 out of 5 starsRated 4.5833 out of 5 stars(48)

Polo Ralph LaurenMen's Ranger Leather Buckle Boots

Permanently Reduced
Orig.
Now
Extended Sizes
Only size 7, 8 available
Rated 4.7875 out of 5 starsRated 4.7875 out of 5 starsRated 4.7875 out of 5 starsRated 4.7875 out of 5 starsRated 4.7875 out of 5 stars(80)

Polo Ralph LaurenMen's Ranger Suede Multi Boots

Permanently Reduced
Orig.
Now
Internet Exclusive
Only size 8 available
Rated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 stars(3)

Johnston & MurphyMen's Barret Suede Plain Toe Boots

Permanently Reduced
Orig.
Now
Extended Sizes
Rated 3.5714 out of 5 starsRated 3.5714 out of 5 starsRated 3.5714 out of 5 starsRated 3.5714 out of 5 starsRated 3.5714 out of 5 stars(7)

Steve MaddenMen's Salvatore Leather Lug Sole Boots

Permanently Reduced
Orig.
Now
Extended Sizes
Rated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 stars(5)

Flag LTD.Men's Ayden Moc Toe Waterproof Leather Lace Up Chukka Boots

Permanently Reduced
Orig.
Now
Dillard's Exclusive

Cole HaanMen's Chamberlin Water Resistant Nubuck Cap Toe Boots

Permanently Reduced
Orig.
Now
Internet Exclusive

Twisted XMen's Leather Lace-Up Chukka Driving Moccasins

Permanently Reduced
Orig.
Now
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)

MerrellMen's Moab 3 Vista Mid Waterproof Mid Hikers

Permanently Reduced
Orig.
Now
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)

Johnston & MurphyMen's Larkin Leather Plain Toe Chukka Boots

Permanently Reduced
Orig.
Now
Extended Sizes
Rated 3.8571 out of 5 starsRated 3.8571 out of 5 starsRated 3.8571 out of 5 starsRated 3.8571 out of 5 starsRated 3.8571 out of 5 stars(7)

COACHMen's Lug Sole Leather Boots

Permanently Reduced
Orig.
Now
Internet Exclusive
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)

UGGMen's Shasta Waterproof Cold Weather Mid Boots

Permanently Reduced
Orig.
Now
Internet Exclusive
Only size 8, 9 available

Cole HaanMen's 2.ZERØGRAND Suede Chukka Boots

Permanently Reduced
Orig.
Now
Internet Exclusive
Rated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 stars(1)

Cole HaanMen's Muir Leather Moc Toe Boots

Permanently Reduced
Orig.
Now
Internet Exclusive

TaftMen's Jack Atlantis Floral Jacquard Calfskin Cap Toe Dress Boots

Permanently Reduced
Orig.
Now
Internet Exclusive
Only size 9.5 available
Rated 4.8824 out of 5 starsRated 4.8824 out of 5 starsRated 4.8824 out of 5 starsRated 4.8824 out of 5 starsRated 4.8824 out of 5 stars(17)

Steve MaddenMen's Walvia Nubuck Lug Sole Work Boots

Permanently Reduced
Orig.
Now
Extended Sizes

EastlandMen's Ethan 1955 Leather Boots

Permanently Reduced
Orig.
Now
Internet Exclusive
Extended Sizes
Only size 9, 12 available
Eastland Men's Jack Chukka BootsMen's Jack Chukka Boots

EastlandMen's Jack Chukka Boots

Permanently Reduced
Orig.
Now
Internet Exclusive
Only size 10 available
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