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chukka boots : Men's Boots

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  • 77 Items
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 4.8817 out of 5 starsRated 4.8817 out of 5 starsRated 4.8817 out of 5 starsRated 4.8817 out of 5 starsRated 4.8817 out of 5 stars(355)
UGG Men's Idyllwild Leather Lace BootsMen's Idyllwild Leather Lace Boots

UGGMen's Idyllwild Leather Lace Boots

Extended Sizes
Johnston & Murphy Men's Calder Leather Chukka Lace Up BootsMen's Calder Leather Chukka Lace Up Boots

Johnston & MurphyMen's Calder Leather Chukka Lace Up Boots

Extended Sizes
Rated 4.5094 out of 5 starsRated 4.5094 out of 5 starsRated 4.5094 out of 5 starsRated 4.5094 out of 5 starsRated 4.5094 out of 5 stars(53)
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 4.6522 out of 5 starsRated 4.6522 out of 5 starsRated 4.6522 out of 5 starsRated 4.6522 out of 5 starsRated 4.6522 out of 5 stars(46)
UGG Men's Neumel Cold Weather Waterproof Hybrid BootsMen's Neumel Cold Weather Waterproof Hybrid Boots

UGGMen's Neumel Cold Weather Waterproof Hybrid Boots

Save on Select Items
Orig.
Now
Extended Sizes
Twisted X Men's Chukka Hiker Waterproof BootsMen's Chukka Hiker Waterproof Boots

Twisted XMen's Chukka Hiker Waterproof 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)
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

Internet Exclusive
Ariat Men's Spitfire BootsMen's Spitfire Boots

AriatMen's Spitfire Boots

Extended Sizes
Rated 4.7227 out of 5 starsRated 4.7227 out of 5 starsRated 4.7227 out of 5 starsRated 4.7227 out of 5 starsRated 4.7227 out of 5 stars(321)
Men's Neumel Classic Fur Lined Suede Lace Up Chukka Boots

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

Extended Sizes
Rated 4.8817 out of 5 starsRated 4.8817 out of 5 starsRated 4.8817 out of 5 starsRated 4.8817 out of 5 starsRated 4.8817 out of 5 stars(355)

Twisted XMen's Driving Woven Moccasin Chukka 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)

FryeMen's Astor Leather Chukka Boots

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)

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

Extended Sizes
Rated 4.8817 out of 5 starsRated 4.8817 out of 5 starsRated 4.8817 out of 5 starsRated 4.8817 out of 5 starsRated 4.8817 out of 5 stars(355)

Bed StuMen's Illiad Leather Chukka Boots

Johnston & MurphyMen's XC+ Durham Waterproof 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(5)

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

Extended Sizes
Rated 4.8817 out of 5 starsRated 4.8817 out of 5 starsRated 4.8817 out of 5 starsRated 4.8817 out of 5 starsRated 4.8817 out of 5 stars(355)

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)

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)

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

Extended Sizes
Rated 4.8817 out of 5 starsRated 4.8817 out of 5 starsRated 4.8817 out of 5 starsRated 4.8817 out of 5 starsRated 4.8817 out of 5 stars(355)

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)

Twisted XMen's Driving Leather Moc Toe Chukka Boots

Extended Sizes

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

Extended Sizes
Rated 4.6378 out of 5 starsRated 4.6378 out of 5 starsRated 4.6378 out of 5 starsRated 4.6378 out of 5 starsRated 4.6378 out of 5 stars(450)

Cole HaanMen's Morse Leather Chukka Boots

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)

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)

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)

BirkenstockMen's Uppsala Mid Suede 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)

ECCOMen's Metropole Milan Suede Chukka 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)

SorelMen's Madson II Waterproof Leather Chukka Boots

Internet Exclusive
Extended Sizes
Rated 4.375 out of 5 starsRated 4.375 out of 5 starsRated 4.375 out of 5 starsRated 4.375 out of 5 starsRated 4.375 out of 5 stars(88)

AriatMen's Spitfire Waterproof Leather 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(48)

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)

AriatMen's Clean Country Suede Chukka Boots

Rated 4.4091 out of 5 starsRated 4.4091 out of 5 starsRated 4.4091 out of 5 starsRated 4.4091 out of 5 starsRated 4.4091 out of 5 stars(22)

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)

SorelMen's Cyprus Waterproof Leather 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 Alvaro Hand Painted Multi Color Ostrich Chukka Boots

Internet Exclusive

Steve MaddenMen's Noby Leather Boots

Internet Exclusive
Extended Sizes
Only size 11 available

AriatMen's Lookout Leather Chukka Boots

Only size 11 available
Rated 4.1159 out of 5 starsRated 4.1159 out of 5 starsRated 4.1159 out of 5 starsRated 4.1159 out of 5 starsRated 4.1159 out of 5 stars(69)

SorelMen's Slabtown 62' Stoic Suede Chukka 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)

TimberlandMen's Redwood Edge 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(2)

AriatMen's Split Rock Leather Moc Toe 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(5)

DannerMen's Logger Moc 917 GTX Waterproof Nubuck Leather 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)

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)

Twisted XMen's Chukka Driving Mocs

Internet Exclusive
Extended Sizes

Dune LondonMen's Smoky Leather Casual Ankle Boots

Internet Exclusive

ALDOMen's Farrell Leather Lace Up Boots

Extended Sizes

Bed StuMen's Lincoln Lace Up Leather Boots

ALIGNMen's Rivers Weatherproof Oiled Leather Flannel Lined Winter Boots

Internet Exclusive

Twisted XMen's Driving Moccasin Chukka 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)

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)

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)

BornMen's Ethan Distressed Suede Boots

Permanently Reduced
Orig.
Now
Extended Sizes

Johnston & MurphyMen's Calder 175th Anniversary Leather Chukka Boots

Permanently Reduced
Orig.
Now
Rated 4.6 out of 5 starsRated 4.6 out of 5 starsRated 4.6 out of 5 starsRated 4.6 out of 5 starsRated 4.6 out of 5 stars(5)

Cole HaanMen's Muir Waterproof Suede Moc Toe Boots

Permanently Reduced
Orig.
Now

Johnston & MurphyMen's Upton Leather Chukka Boots

Permanently Reduced
Orig.
Now
Extended Sizes

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

Permanently Reduced
Orig.
Now
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)

COACHMen's Lug Sole Leather Boots

Permanently Reduced
Orig.
Now
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)

SkechersMen's Slip-ins Relaxed Fit: Respected 2.0 - Hagler Boots

Permanently Reduced
Orig.
Now
Extended Sizes
Only size 8, 10 available

L.L.BeanMen's Allagash Handsewn Leather Chukka Boots

Permanently Reduced
Orig.
Now
Rated 3.9189 out of 5 starsRated 3.9189 out of 5 starsRated 3.9189 out of 5 starsRated 3.9189 out of 5 starsRated 3.9189 out of 5 stars(37)

To Boot New YorkMen's Vista Chukka Boots

Permanently Reduced
Orig.
Now
Extended Sizes

Johnston & MurphyMen's Barret Suede Plain Toe Boots

Permanently Reduced
Orig.
Now
Internet Exclusive
Extended Sizes
Rated 3.75 out of 5 starsRated 3.75 out of 5 starsRated 3.75 out of 5 starsRated 3.75 out of 5 starsRated 3.75 out of 5 stars(8)

BornMen's Brock Distressed Suede Boots

Permanently Reduced
Orig.
Now
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(9)

Steve MaddenMen's Jotting Leather Contrast Stitch Cap Toe Boots

Permanently Reduced
Orig.
Now
Internet Exclusive
Only size 7 available
Rated 4.8333 out of 5 starsRated 4.8333 out of 5 starsRated 4.8333 out of 5 starsRated 4.8333 out of 5 starsRated 4.8333 out of 5 stars(6)

ALIGNMen's Rivers Weatherproof Tumbled Leather Boots

Permanently Reduced
Orig.
Now

Polo Ralph LaurenMen's Ranger Work Boots

Permanently Reduced
Orig.
Now
Internet Exclusive
Extended Sizes
Rated 4.9 out of 5 starsRated 4.9 out of 5 starsRated 4.9 out of 5 starsRated 4.9 out of 5 starsRated 4.9 out of 5 stars(10)

Johnston & MurphyMen's Braxton Oiled 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)

TimberlandMen's Redwood Falls Waterproof Leather Chukka Boots

Permanently Reduced
Orig.
Now
Internet Exclusive
Extended Sizes
Only size 11.5 available
Rated 4.3768 out of 5 starsRated 4.3768 out of 5 starsRated 4.3768 out of 5 starsRated 4.3768 out of 5 starsRated 4.3768 out of 5 stars(69)

UGGMen's Lug Chukka Boots

Permanently Reduced
Orig.
Now
Internet Exclusive
Extended Sizes
Only size 10 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(1)

SorelMen's Slabtown 62 Moc Waterproof Boots

Permanently Reduced
Orig.
Now
Extended Sizes
Rated 4.4211 out of 5 starsRated 4.4211 out of 5 starsRated 4.4211 out of 5 starsRated 4.4211 out of 5 starsRated 4.4211 out of 5 stars(38)

Cole HaanMen's Muir Leather Moc Toe Boots

Permanently Reduced
Orig.
Now
Internet Exclusive

Johnston & MurphyMen's Barret Leather Plain Toe Boots

Permanently Reduced
Orig.
Now
Extended Sizes
Rated 4.1429 out of 5 starsRated 4.1429 out of 5 starsRated 4.1429 out of 5 starsRated 4.1429 out of 5 starsRated 4.1429 out of 5 stars(7)

Steve MaddenMen's Tabriz Lace Up Leather Chukka Boots

Permanently Reduced
Orig.
Now
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)

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

Permanently Reduced
Orig.
Now
Dillard's Exclusive

Polo Ralph LaurenMen's Asher Suede Chukka Boots

Permanently Reduced
Orig.
Now
Internet Exclusive
Only size 8.5, 11 available

Johnston & MurphyMen's Larkin Leather Plain Toe Chukka Boots

Permanently Reduced
Orig.
Now
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(10)

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

Permanently Reduced
Orig.
Now
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)

UGGMen's Chukka Lug Suede Boots

Permanently Reduced
Orig.
Now
Extended Sizes
Only size 11 available

Polo Ralph LaurenMen's Ranger Suede Patch Detail Boots

Permanently Reduced
Orig.
Now
Internet Exclusive
Only size 8.5, 9 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 X Men's Leather Lace-Up Chukka Driving MoccasinsMen's Leather Lace-Up Chukka Driving Moccasins

Twisted XMen's Leather Lace-Up Chukka Driving Moccasins

Permanently Reduced
Orig.
Now
Extended Sizes
Only size 10 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(3)
  • 77 Items

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