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1 : Men's Chukka Shoes

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clear allChukkaclear filter
  • 91 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 4.8807 out of 5 starsRated 4.8807 out of 5 starsRated 4.8807 out of 5 starsRated 4.8807 out of 5 starsRated 4.8807 out of 5 stars(352)
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
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 4.6444 out of 5 starsRated 4.6444 out of 5 starsRated 4.6444 out of 5 starsRated 4.6444 out of 5 starsRated 4.6444 out of 5 stars(45)
UGG Men's Idyllwild Leather Lace BootsMen's Idyllwild Leather Lace Boots

UGGMen's Idyllwild Leather Lace Boots

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

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)
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 4.4902 out of 5 starsRated 4.4902 out of 5 starsRated 4.4902 out of 5 starsRated 4.4902 out of 5 starsRated 4.4902 out of 5 stars(51)
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)
L.L.Bean Men's Stonington Leather Moc Toe BootsMen's Stonington Leather Moc Toe Boots

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

Extended Sizes
Rated 4.6349 out of 5 starsRated 4.6349 out of 5 starsRated 4.6349 out of 5 starsRated 4.6349 out of 5 starsRated 4.6349 out of 5 stars(430)
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 4.8807 out of 5 starsRated 4.8807 out of 5 starsRated 4.8807 out of 5 starsRated 4.8807 out of 5 starsRated 4.8807 out of 5 stars(352)

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)

AriatMen's Spitfire Boots

Extended Sizes
Rated 4.7063 out of 5 starsRated 4.7063 out of 5 starsRated 4.7063 out of 5 starsRated 4.7063 out of 5 starsRated 4.7063 out of 5 stars(303)

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

Extended Sizes
Rated 4.8807 out of 5 starsRated 4.8807 out of 5 starsRated 4.8807 out of 5 starsRated 4.8807 out of 5 starsRated 4.8807 out of 5 stars(352)

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)

Steve MaddenMen's Noby Leather Boots

Extended Sizes

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

Extended Sizes
Rated 4.8807 out of 5 starsRated 4.8807 out of 5 starsRated 4.8807 out of 5 starsRated 4.8807 out of 5 starsRated 4.8807 out of 5 stars(352)

BirkenstockMen's Uppsala Mid Suede Boots

Bed StuMen's Lincoln Lace Up Leather Boots

Internet Exclusive

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

Extended Sizes
Rated 4.8807 out of 5 starsRated 4.8807 out of 5 starsRated 4.8807 out of 5 starsRated 4.8807 out of 5 starsRated 4.8807 out of 5 stars(352)

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)

Twisted XMen's Chukka Driving Mocs

Internet Exclusive
Extended Sizes

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)

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)

BornMen's Ethan Distressed Suede Boots

Extended Sizes

ECCOMen's Metropole Milan Suede Chukka Boots

Twisted XMen's Cellstretch® Wedge Sole Boots

Extended Sizes

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

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

Rated 3.9118 out of 5 starsRated 3.9118 out of 5 starsRated 3.9118 out of 5 starsRated 3.9118 out of 5 starsRated 3.9118 out of 5 stars(34)

SorelMen's Madson II Moc Toe Waterproof Boots

Internet Exclusive
Only size 8, 14 available
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)

AriatMen's Clean Country Suede Chukka Boots

Rated 4.381 out of 5 starsRated 4.381 out of 5 starsRated 4.381 out of 5 starsRated 4.381 out of 5 starsRated 4.381 out of 5 stars(21)

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)

Cole HaanMen's Morse Leather Chukka Boots

Twisted XMen's Driving Moccasin Chukka Boots

Internet Exclusive
Extended Sizes

Cole HaanMen's Chamberlin Water Resistant Nubuck Chukka Boots

Internet Exclusive

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

Twisted XMen's Chukka Driving Mocs

Internet Exclusive
Extended Sizes

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)

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)

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)

TimberlandMen's Redwood Edge Leather Lace Up Boots

Extended Sizes

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)

Steve MaddenMen's Harros Leather Chukka Boots

Internet Exclusive
Only size 13 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)

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

Extended Sizes

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)

TimberlandMen's Redwood Falls Waterproof Leather Chukka Boots

Internet Exclusive
Extended Sizes
Rated 4.3387 out of 5 starsRated 4.3387 out of 5 starsRated 4.3387 out of 5 starsRated 4.3387 out of 5 starsRated 4.3387 out of 5 stars(62)

Steve MaddenMen's Daviston Lace Up Leather Chukka 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 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

SorelMen's Cyprus Waterproof Leather Boots

Internet Exclusive
Extended Sizes

ALDOMen's Farrell Leather Lace Up Boots

Internet Exclusive
Extended Sizes

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)

SorelMen's Slabtown 62 Moc Waterproof Boots

Internet Exclusive
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)

Twisted XMen's Waterproof Driving Moccasins Chukka Boots

Internet Exclusive
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 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)

DannerMen's Logger Moc 917 GTX Waterproof Nubuck Leather Boots

Internet Exclusive
Extended Sizes

To Boot New YorkMen's Vista Chukka 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)

Twisted XMen's Work Composite Toe Slip On Driving Moccasins

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)

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 XMen's Chukka Driving Mocs

Internet Exclusive
Extended Sizes

COACHMen's Sculpt C Suede Chukka Oxfords

Internet Exclusive

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)

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 Flannel Lined Winter 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)

Dune LondonMen's Smoky Leather Casual Ankle Boots

Internet Exclusive

Twisted XMen's Chukka Driving Mocs

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)

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)

UGGMen's Chukka Lug Suede Boots

Permanently Reduced
Orig.
Now
Extended Sizes

Steve MaddenMen's Jotting Leather Contrast Stitch Cap Toe Boots

Permanently Reduced
Orig.
Now
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)

Polo Ralph LaurenMen's Ranger Work 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(8)

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)

BornMen's Brock Distressed Suede 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(9)

Cole HaanMen's Muir Waterproof Suede Moc Toe Boots

Permanently Reduced
Orig.
Now
Internet Exclusive

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

Permanently Reduced
Orig.
Now
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(5)

Johnston & MurphyMen's Upton Leather Chukka Boots

Permanently Reduced
Orig.
Now
Extended Sizes

Steve MaddenMen's Tabriz Lace Up Leather Chukka Boots

Permanently Reduced
Orig.
Now
Extended Sizes

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)

Johnston & MurphyMen's Barret Leather Plain Toe Boots

Permanently Reduced
Orig.
Now
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)

Polo Ralph LaurenMen's Ranger Suede Patch Detail Boots

Permanently Reduced
Orig.
Now
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)

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)

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 Asher Suede Chukka Boots

Permanently Reduced
Orig.
Now

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

Permanently Reduced
Orig.
Now
Dillard's Exclusive

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)

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)

Polo Ralph LaurenMen's Ranger Suede Multi Boots

Permanently Reduced
Orig.
Now
Internet Exclusive
Only size 8 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(3)

UGGMen's Neumel Crafted Regenerate Boots

Permanently Reduced
Orig.
Now
Only size 10 available

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)

Cole HaanMen's 2.ZERØGRAND Suede Chukka Boots

Permanently Reduced
Orig.
Now
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)

Johnston & MurphyMen's Larkin Leather Plain Toe Chukka Boots

Permanently Reduced
Orig.
Now
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)

ALIGNMen's Rivers Weatherproof Tumbled Leather Boots

Permanently Reduced
Orig.
Now

Cole HaanMen's Muir Leather Moc Toe Boots

Permanently Reduced
Orig.
Now
Internet Exclusive
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
  • 91 Items

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