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clear allChukkaclear filter
  • 93 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

Save on Select Items
Orig.
Now
Extended Sizes
Rated 4.88 out of 5 starsRated 4.88 out of 5 starsRated 4.88 out of 5 starsRated 4.88 out of 5 starsRated 4.88 out of 5 stars(350)
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 4.6364 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(44)
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 4.5217 out of 5 starsRated 4.5217 out of 5 starsRated 4.5217 out of 5 starsRated 4.5217 out of 5 starsRated 4.5217 out of 5 stars(46)
Polo Ralph Lauren Men's Ranger Suede and Twill Patch Detail BootsMen's Ranger Suede and Twill Patch Detail Boots

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

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

Twisted XMen's Driving Leather Moccasin 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(8)
Steve Madden Men's Jotting Leather Contrast Stitch Cap Toe BootsMen's Jotting Leather Contrast Stitch Cap Toe Boots

Steve MaddenMen's Jotting Leather Contrast Stitch Cap Toe 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(4)
Steve Madden Men's Harros Leather Chukka BootsMen's Harros Leather Chukka Boots

Steve MaddenMen's Harros Leather 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(2)
Twisted X Men's Driving Woven Moccasin Chukka BootsMen's Driving Woven Moccasin Chukka Boots

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

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

Save on Select Items
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Now
Extended Sizes
Rated 4.88 out of 5 starsRated 4.88 out of 5 starsRated 4.88 out of 5 starsRated 4.88 out of 5 starsRated 4.88 out of 5 stars(350)

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

UGGMen's Idyllwild Leather Lace Boots

Extended Sizes

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

Save on Select Items
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Rated 4.88 out of 5 starsRated 4.88 out of 5 starsRated 4.88 out of 5 starsRated 4.88 out of 5 starsRated 4.88 out of 5 stars(350)

BornMen's Brock Distressed Suede 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(9)

BirkenstockMen's Utti Lace Up Chukkas

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(4)

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

Save on Select Items
Orig.
Now
Extended Sizes
Rated 4.88 out of 5 starsRated 4.88 out of 5 starsRated 4.88 out of 5 starsRated 4.88 out of 5 starsRated 4.88 out of 5 stars(350)

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

Extended Sizes
Rated 4.6321 out of 5 starsRated 4.6321 out of 5 starsRated 4.6321 out of 5 starsRated 4.6321 out of 5 starsRated 4.6321 out of 5 stars(424)

SorelMen's Madson II Waterproof Leather Chukka Boots

Internet Exclusive
Extended Sizes
Rated 4.3678 out of 5 starsRated 4.3678 out of 5 starsRated 4.3678 out of 5 starsRated 4.3678 out of 5 starsRated 4.3678 out of 5 stars(87)

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

Save on Select Items
Orig.
Now
Extended Sizes
Rated 4.88 out of 5 starsRated 4.88 out of 5 starsRated 4.88 out of 5 starsRated 4.88 out of 5 starsRated 4.88 out of 5 stars(350)

Johnston & MurphyMen's Barret Leather Plain Toe 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)

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

Johnston & MurphyMen's Braxton Oiled Leather Chukka 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 Driving Leather Moc Toe Chukka Boots

Internet Exclusive
Extended Sizes

SorelMen's Cyprus Waterproof Leather Boots

Extended Sizes

BornMen's Ethan Distressed Suede Boots

Extended Sizes

Steve MaddenMen's Noby Leather Boots

Extended Sizes

AriatMen's Spitfire Boots

Extended Sizes
Rated 4.7053 out of 5 starsRated 4.7053 out of 5 starsRated 4.7053 out of 5 starsRated 4.7053 out of 5 starsRated 4.7053 out of 5 stars(302)

AriatMen's Spitfire Waterproof Leather Boots

Extended Sizes
Rated 4.4524 out of 5 starsRated 4.4524 out of 5 starsRated 4.4524 out of 5 starsRated 4.4524 out of 5 starsRated 4.4524 out of 5 stars(42)

COACHMen's Lug Sole Leather 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)

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)

Polo Ralph LaurenMen's Ranger Leather Buckle Boots

Internet Exclusive
Extended Sizes
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)

UGGMen's Neumel Cold Weather Hybrd Boots

Extended Sizes

L.L.BeanL.L. Bean Men's Allagash Handsewn Leather Chukka 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(32)

BirkenstockMen's Uppsala Mid Suede 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(2)

Johnston & MurphyMen's Barret Suede Plain Toe Boots

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)

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

Dillard's Exclusive

SorelMen's Slabtown 62 Moc Waterproof Boots

Internet Exclusive
Extended Sizes
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(35)

Johnston & MurphyMen's Upton Leather Chukka Boots

Extended Sizes

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)

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)

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)

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)

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)

Twisted XMen's Chukka Driving Mocs

Internet Exclusive
Extended Sizes

Cole HaanMen's Chamberlin Water Resistant Nubuck Chukka Boots

Internet Exclusive

Twisted XMen's Chukka Driving CellStretch Mocs

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 Chukka Driving Mocs

Extended Sizes

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

Extended Sizes
Rated 4.7526 out of 5 starsRated 4.7526 out of 5 starsRated 4.7526 out of 5 starsRated 4.7526 out of 5 starsRated 4.7526 out of 5 stars(97)

AriatMen's Clean Country Suede Chukka Boots

Rated 4.35 out of 5 starsRated 4.35 out of 5 starsRated 4.35 out of 5 starsRated 4.35 out of 5 starsRated 4.35 out of 5 stars(20)

ALIGNMen's Rivers Weatherproof Tumbled Leather Boots

TimberlandMen's Redwood Edge Leather Lace Up Boots

Extended Sizes

Steve MaddenMen's Daviston Lace Up Leather Chukka Boots

Internet Exclusive
Extended Sizes

AriatMen's Split Rock Leather Moc Toe Chukka Boots

Polo Ralph LaurenMen's Ranger 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(8)

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)

Polo Ralph LaurenMen's Ranger Suede Multi 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)

Polo Ralph LaurenMen's Ranger Suede and Plaid Wool Boots

Internet Exclusive
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(2)

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)

ECCOMen's Metropole Milan Suede Chukka Boots

Cole HaanMen's Morse Leather Chukka Boots

Twisted XMen's Cellstretch® Wedge Sole Boots

Extended Sizes

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

TimberlandMen's Redwood Falls Waterproof Leather Chukka Boots

Internet Exclusive
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)

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)

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 Chukka Driving Mocs

Extended Sizes

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)

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)

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)

Polo Ralph LaurenMen's Asher Suede Chukka Boots

Internet Exclusive

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)

Cole HaanMen's Muir Waterproof Suede Moc Toe 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)

Twisted XMen's Chukka Driving Mocs

Extended Sizes

Twisted XMen's Work Steel Toe Leather Chukka Driving Moccasins

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 Illiad Leather Chukka Boots

Twisted XMen's Driving Moccasin Chukka Boots

Internet Exclusive
Extended Sizes

Bed StuMen's Lincoln Lace Up Leather Boots

Cole HaanMen's Muir Leather Moc Toe Boots

Internet Exclusive

COACHMen's Sculpt C Suede Chukka Oxfords

Internet Exclusive

Dune LondonMen's Smoky Leather Casual Ankle Boots

Internet Exclusive

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)

ALDOMen's Farrell Leather Lace Up Boots

Internet Exclusive
Extended Sizes

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)

ALIGNMen's Rivers Weatherproof Oiled Leather Boots

Internet Exclusive

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 Jack Chukka Boots

Internet Exclusive
Only size 10 available

BornMen's Harrison Leather Chukka Boots

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)

UGGMen's Chukka Lug Suede Boots

Permanently Reduced
Orig.
Now
Extended Sizes

UGGMen's Neumel Crafted Regenerate Boots

Permanently Reduced
Orig.
Now

UGGMen's Lug 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)

Steve MaddenMen's Tabriz Lace Up Leather Chukka Boots

Permanently Reduced
Orig.
Now
Extended Sizes

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)

Johnston & MurphyMen's Larkin Leather Plain Toe Chukka Boots

Permanently Reduced
Orig.
Now
Extended Sizes
Cole Haan Men's 2.ZERØGRAND Suede Chukka BootsMen's 2.ZERØGRAND Suede Chukka Boots

Cole HaanMen's 2.ZERØGRAND Suede Chukka Boots

Permanently Reduced
Orig.
Now
  • 93 Items

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