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  • 89 Items
Born Analia Distressed Suede Ankle Chukka BootiesAnalia Distressed Suede Ankle Chukka Booties

BornAnalia Distressed Suede Ankle Chukka Booties

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(14)
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 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 4.8814 out of 5 starsRated 4.8814 out of 5 starsRated 4.8814 out of 5 starsRated 4.8814 out of 5 starsRated 4.8814 out of 5 stars(354)
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)
UGG Men's Idyllwild Leather Lace BootsMen's Idyllwild Leather Lace Boots

UGGMen's Idyllwild Leather Lace Boots

Extended Sizes
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
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 4.6384 out of 5 starsRated 4.6384 out of 5 starsRated 4.6384 out of 5 starsRated 4.6384 out of 5 starsRated 4.6384 out of 5 stars(437)
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(3)
Analia Distressed Suede Ankle Chukka Booties

PLACEHOLDERAnalia Distressed Suede Ankle Chukka Booties

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(14)

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 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)

PLACEHOLDERAnalia Distressed Suede Ankle Chukka Booties

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(14)

Twisted XMen's Chukka Driving Mocs

Internet Exclusive
Extended Sizes

Twisted XMen's Driving Leather Moc Toe Chukka Boots

Extended Sizes

PLACEHOLDERAnalia Distressed Suede Ankle Chukka Booties

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(14)

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)

Bed StuMen's Lincoln Lace Up Leather Boots

PLACEHOLDERAnalia Distressed Suede Ankle Chukka Booties

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(14)

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)

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(4)

DannerWomen's Inquire Chukka Waterproof Suede Hiking Boots

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

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

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)

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)

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)

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 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)

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)

AriatMen's Spitfire Waterproof Leather Boots

Extended Sizes
Rated 4.4651 out of 5 starsRated 4.4651 out of 5 starsRated 4.4651 out of 5 starsRated 4.4651 out of 5 starsRated 4.4651 out of 5 stars(43)

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)

AriatMen's Spitfire Boots

Extended Sizes
Rated 4.7101 out of 5 starsRated 4.7101 out of 5 starsRated 4.7101 out of 5 starsRated 4.7101 out of 5 starsRated 4.7101 out of 5 stars(307)

Cole HaanMen's Morse Leather Chukka Boots

DannerWomen's Inquire Chukka Waterproof Leather Hiking Boots

Extended Sizes

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)

Cole HaanMen's Chamberlin Water Resistant Nubuck Chukka Boots

Internet Exclusive

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 Chukka Driving Mocs

Internet Exclusive
Extended Sizes

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)

DannerMen's Logger Moc 917 GTX Waterproof Nubuck Leather Boots

Internet Exclusive
Extended Sizes

Twisted XMen's Driving Moccasin Chukka Boots

Internet Exclusive
Extended Sizes

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)

ECCOMen's Metropole Milan Suede Chukka Boots

Dune LondonMen's Smoky Leather Casual Ankle Boots

Internet Exclusive

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)

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 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)

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 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)

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)

ALDOMen's Farrell Leather Lace Up Boots

Extended Sizes

Bed StuMen's Illiad Leather Chukka Boots

Twisted XMen's Chukka Driving Mocs

Extended Sizes

MinnetonkaWomen's Torrey Suede Faux Shearling Bootie Slippers

Extended Sizes

Twisted XWomen's Sunflower Leather Driving Moc Toe Chukka Boots

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)

MinnetonkaKids' Suede Fringe Detail Tramper Boots (Toddler)

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)

MinnetonkaKids' Suede Fringe Softsole Boots (Toddler)

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 XWomen's Tooled Turquoise Stud Driving Moc Toe Chukka 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(5)

Kurt Geiger LondonMansion Cozy Studded Suede Bit Buckle Platform Boots

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(9)

UGGEsmee Lace Up Suede Platform Booties

Permanently Reduced
Orig.
Now
Extended Sizes
Only size 9, 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(4)

UGGMen's Chukka Lug Suede Boots

Permanently Reduced
Orig.
Now
Extended Sizes

BirkenstockWomen's Uppsala Shearling Lined Suede Chukka Booties

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(6)

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)

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

Permanently Reduced
Orig.
Now
Extended Sizes

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

Permanently Reduced
Orig.
Now
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)

To Boot New YorkMen's Vista Chukka Boots

Permanently Reduced
Orig.
Now
Internet Exclusive
Extended Sizes

Johnston & MurphyMen's Upton Leather Chukka Boots

Permanently Reduced
Orig.
Now
Extended Sizes

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)

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)

BornMen's Ethan Distressed Suede 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)

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

Permanently Reduced
Orig.
Now
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(4)

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(2)

Cole HaanMen's Muir Leather Moc Toe Boots

Permanently Reduced
Orig.
Now
Internet Exclusive

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)

Steve MaddenMen's Tabriz Lace Up Leather Chukka Boots

Permanently Reduced
Orig.
Now
Extended Sizes

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(9)

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

Permanently Reduced
Orig.
Now
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)

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 Waterproof Suede Moc Toe Boots

Permanently Reduced
Orig.
Now

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)

ALIGNMen's Rivers Weatherproof Tumbled Leather 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

Gentle SoulsCacti Suede Ankle Booties

Permanently Reduced
Orig.
Now
Extended Sizes

Stride RiteBoys' Quinn SRT Leather Boots (Toddler)

Permanently Reduced
Orig.
Now
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)

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)

COACHMen's Sculpt C Suede Chukka Oxfords

Permanently Reduced
Orig.
Now
Internet Exclusive
Johnston & Murphy Men's Barret Suede Plain Toe BootsMen's Barret Suede Plain Toe Boots

Johnston & MurphyMen's Barret Suede Plain Toe Boots

Permanently Reduced
Orig.
Now
Internet Exclusive
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)
  • 89 Items

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