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  • 119 Items
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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 4.88 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)
Birkenstock Women's Uppsala Mid Suede Lace Up BootiesWomen's Uppsala Mid Suede Lace Up Booties

BirkenstockWomen's Uppsala Mid Suede Lace Up Booties

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 & 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 4.5417 out of 5 starsRated 4.5417 out of 5 starsRated 4.5417 out of 5 starsRated 4.5417 out of 5 starsRated 4.5417 out of 5 stars(48)
Born Analia Distressed Suede Ankle Chukka BootiesAnalia Distressed Suede Ankle Chukka Booties

BornAnalia Distressed Suede Ankle Chukka Booties

Extended Sizes
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(10)
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)
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)
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)
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 4.88 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)

ClarksOriginal Wallabee Suede Chukka Booties

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)

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

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)

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)

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

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)

Twisted XWomen's Tooled Moc Toe Driving Chukka Booties

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 Neumel Cold Weather Hybrd Boots

Extended Sizes

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

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)

UGGMen's Idyllwild Leather Lace Boots

Extended Sizes

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)

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)

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)

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)

BirkenstockWomen's Uppsala Shearling Lined Suede Chukka Booties

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(4)

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)

Steve MaddenLeon Suede Bit Buckle High-Top Platform Loafers

Extended Sizes
Rated 3.8 out of 5 starsRated 3.8 out of 5 starsRated 3.8 out of 5 starsRated 3.8 out of 5 starsRated 3.8 out of 5 stars(15)

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(33)

TimberlandWomen's Stone Street Leather Kiltie Lace Up Boots

Internet Exclusive
Extended Sizes
Rated 4.7619 out of 5 starsRated 4.7619 out of 5 starsRated 4.7619 out of 5 starsRated 4.7619 out of 5 starsRated 4.7619 out of 5 stars(42)

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)

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)

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 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)

BornMen's Ethan Distressed Suede Boots

Extended Sizes

Johnston & MurphyBoys' McGuffey Leather Alternative Closure Chukka Boots (Toddler)

Rated 4.9231 out of 5 starsRated 4.9231 out of 5 starsRated 4.9231 out of 5 starsRated 4.9231 out of 5 starsRated 4.9231 out of 5 stars(13)

SASGretchen Water Resistant Leather Lace Up Booties

Extended Sizes

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)

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)

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)

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)

Polo Ralph LaurenMen's Ranger Leather Buckle Boots

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)

RykaWomen's Vibrant Washable Chukka Platform Ankle Booties

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(2)

Twisted XMen's Chukka Driving Mocs

Extended Sizes

Twisted XMen's Driving Leather Moc Toe Chukka Boots

Internet Exclusive
Extended Sizes

Twisted XWomen's Original Leather Driving Moc Toe Chukka Boots

Extended Sizes
Rated 4.5882 out of 5 starsRated 4.5882 out of 5 starsRated 4.5882 out of 5 starsRated 4.5882 out of 5 starsRated 4.5882 out of 5 stars(17)

SASKich Nubuck Lace Up Ankle Wedge Booties

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 XWomen's Embroidered Leather Driving Moc Toe 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(7)

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)

Twisted XMen's Cellstretch® Wedge Sole Boots

Extended Sizes

Polo Ralph LaurenMen's Asher Suede Chukka Boots

Internet Exclusive

Steve MaddenMen's Noby Leather Boots

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)

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)

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)

MinnetonkaWomen's Torrey Suede Faux Shearling Bootie Slippers

Extended Sizes

Johnston & MurphyMen's Upton Leather Chukka Boots

Extended Sizes

Stride RiteBoys' Quinn SRT Leather Boots (Toddler)

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(1)

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)

Johnston & MurphyBoys' Calder Leather Hook-and-Loop Chukka Boots (Toddler)

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)

RykaWomen's Belfast Hiker-Inspired Booties

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(15)

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)

Steve MaddenLeon Leather Bit Buckle High-Top Platform Loafers

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)

Gentle SoulsCacti Suede Ankle Booties

Save on Select Items
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Extended Sizes

ALIGNMen's Rivers Weatherproof Tumbled Leather Boots

Steve MaddenMen's Daviston Lace Up Leather Chukka Boots

Internet Exclusive
Extended Sizes

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(1)

TimberlandMen's Redwood Edge Leather Lace Up Boots

Extended Sizes

DannerWomen's Inquire Chukka Waterproof Suede Hiking Boots

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)

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)

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)

Gentle SoulsBaden Suede Monk Strap Hardware Booties

Internet Exclusive
Extended Sizes

ECCOMen's Metropole Milan Suede Chukka Boots

Cole HaanMen's Chamberlin Water Resistant Nubuck Chukka Boots

Internet Exclusive

Vintage HavanaGrand Suede Platform Booties

Extended Sizes

Cole HaanMen's Morse Leather Chukka Boots

TimberlandWomen's Rowan Way Warm-Lined Water-Resistant Chukka Booties

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)

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)

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

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)

TimberlandWomen's Stone Street Mid Lace Up Waterproof Chukka Booties

Internet Exclusive
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)

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

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)

Dr. Scholl'sOriginal Chic Platform Booties

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(8)

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)

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)

Cole HaanMen's Muir Waterproof Suede Moc Toe Boots

Internet Exclusive

DannerWomen's Inquire Chukka Waterproof Leather Hiking Boots

Extended Sizes

Twisted XMen's Chukka Driving Mocs

Extended Sizes

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)

Bed StuMen's Lincoln Lace Up Leather Boots

COACHMen's Sculpt C Suede Chukka Oxfords

Internet Exclusive

Twisted XMen's Driving Moccasin 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)

Cole HaanMen's Muir Leather Moc Toe Boots

Internet Exclusive

Twisted XWomen's Printed Leather Driving Moc Toe 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(2)

Twisted XWomen's Sunflower Leather Driving Moc Toe Chukka Boots

Internet Exclusive
Extended Sizes
Rated 3.0 out of 5 starsRated 3.0 out of 5 starsRated 3.0 out of 5 starsRated 3.0 out of 5 starsRated 3.0 out of 5 stars(2)
To Boot New York Men's Vista Chukka BootsMen's Vista Chukka Boots

To Boot New YorkMen's Vista Chukka Boots

Internet Exclusive
Extended Sizes
  • 119 Items
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