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  • 96 Items
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 4.6596 out of 5 starsRated 4.6596 out of 5 starsRated 4.6596 out of 5 starsRated 4.6596 out of 5 starsRated 4.6596 out of 5 stars(47)
Josef Seibel Men's Earl 04 Leather Lace Up Chukka BootsMen's Earl 04 Leather Lace Up Chukka 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)
Johnston & Murphy Boys' Calder Leather Lace Up Chukka Boots (Youth)Boys' Calder Leather Lace Up Chukka Boots (Youth)

Johnston & MurphyBoys' Calder Leather Lace Up Chukka Boots (Youth)

Save on Select Items
Orig.
Now
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)
Bed Stu Men's Lincoln Lace Up Leather BootsMen's Lincoln Lace Up Leather Boots

Bed StuMen's Lincoln Lace Up Leather Boots

Internet Exclusive
Born Calyn Distressed Leather Lace Ankle BootiesCalyn Distressed Leather Lace Ankle Booties

BornCalyn Distressed Leather Lace Ankle Booties

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)
Johnston & Murphy Men's XC+ Durham Waterproof Leather Cap Toe BootsMen's XC+ Durham Waterproof Leather Cap Toe Boots

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

Extended Sizes
Rated 4.8571 out of 5 starsRated 4.8571 out of 5 starsRated 4.8571 out of 5 starsRated 4.8571 out of 5 starsRated 4.8571 out of 5 stars(7)
Twisted X Men's Driving Woven Leather Moccasin Chukka BootsMen's Driving Woven Leather Moccasin Chukka Boots

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)
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 4.2857 out of 5 starsRated 4.2857 out of 5 starsRated 4.2857 out of 5 starsRated 4.2857 out of 5 starsRated 4.2857 out of 5 stars(63)
Men's Ranger Tumbled Leather Buckle Lug Sole Boots

PLACEHOLDERMen's Ranger Tumbled Leather Buckle Lug Sole Boots

Extended Sizes
Rated 4.6596 out of 5 starsRated 4.6596 out of 5 starsRated 4.6596 out of 5 starsRated 4.6596 out of 5 starsRated 4.6596 out of 5 stars(47)

BirkenstockMen's Uppsala Mid Suede 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)

TimberlandWomen's Stone Street Leather Kiltie 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(17)

PLACEHOLDERMen's Ranger Tumbled Leather Buckle Lug Sole Boots

Extended Sizes
Rated 4.6596 out of 5 starsRated 4.6596 out of 5 starsRated 4.6596 out of 5 starsRated 4.6596 out of 5 starsRated 4.6596 out of 5 stars(47)

Twisted XMen's Driving Leather Moc Toe Chukka Boots

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 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)

PLACEHOLDERMen's Ranger Tumbled Leather Buckle Lug Sole Boots

Extended Sizes
Rated 4.6596 out of 5 starsRated 4.6596 out of 5 starsRated 4.6596 out of 5 starsRated 4.6596 out of 5 starsRated 4.6596 out of 5 stars(47)

ClarksOriginal Wallabee Suede Chukka Booties

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)

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(8)

PLACEHOLDERMen's Ranger Tumbled Leather Buckle Lug Sole Boots

Extended Sizes
Rated 4.6596 out of 5 starsRated 4.6596 out of 5 starsRated 4.6596 out of 5 starsRated 4.6596 out of 5 starsRated 4.6596 out of 5 stars(47)

BornAnalia Distressed Suede Ankle Chukka Booties

Extended Sizes
Rated 4.2609 out of 5 starsRated 4.2609 out of 5 starsRated 4.2609 out of 5 starsRated 4.2609 out of 5 starsRated 4.2609 out of 5 stars(23)

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

Extended Sizes
Rated 4.6269 out of 5 starsRated 4.6269 out of 5 starsRated 4.6269 out of 5 starsRated 4.6269 out of 5 starsRated 4.6269 out of 5 stars(469)

Flag LTD.Boys' Freddie Nubuck Lace Up Boots (Youth)

Dillard's Exclusive
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)

UGGMen's Idyllwild Leather Lace 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)

AriatMen's Clean Country Suede Chukka Boots

Rated 4.4815 out of 5 starsRated 4.4815 out of 5 starsRated 4.4815 out of 5 starsRated 4.4815 out of 5 starsRated 4.4815 out of 5 stars(27)

DanskoXP 2.0 Clog Leather Booties

Internet Exclusive

Johnston & MurphyMen's Clint Leather Chukka Boots

Internet Exclusive

Cole HaanMen's Chamberlin Water Resistant Nubuck Chukka Boots

DannerMen's Logger Moc 917 GTX Waterproof Nubuck Leather Boots

Internet Exclusive
Extended Sizes

BornBasin Suede Chukka Booties

Internet Exclusive

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(12)

TimberlandWomen's Stone Street Mid Lace Up Waterproof Chukka Booties

Internet Exclusive
Extended Sizes
Rated 4.6111 out of 5 starsRated 4.6111 out of 5 starsRated 4.6111 out of 5 starsRated 4.6111 out of 5 starsRated 4.6111 out of 5 stars(18)

AriatMen's Spitfire Boots

Extended Sizes
Rated 4.7464 out of 5 starsRated 4.7464 out of 5 starsRated 4.7464 out of 5 starsRated 4.7464 out of 5 starsRated 4.7464 out of 5 stars(351)

Johnston & MurphyMens XC+ Durham Wingtip Waterproof Boots

Internet Exclusive

AriatMen's Spitfire Waterproof Leather Boots

Extended Sizes
Rated 4.4762 out of 5 starsRated 4.4762 out of 5 starsRated 4.4762 out of 5 starsRated 4.4762 out of 5 starsRated 4.4762 out of 5 stars(63)

Dr. MartensMen's Lowell Chukka Boots

Internet Exclusive

SASGretchen Water Resistant Leather Lace Up Booties

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(4)

Gentle SoulsBaden Suede Monk Strap Hardware Booties

Internet Exclusive
Extended Sizes

FryeMen's Paul 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 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 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)

UGGMen's Neumel Cold Weather Waterproof Hybrid Boots

Extended Sizes

Dune LondonMen's Smoky Leather Casual Ankle Boots

UGGKids' Neumel Weather Hybrid Boots (Youth)

Internet Exclusive
Only size 4 Youth available

DannerWomen's Inquire Chukka Waterproof Leather Hiking Boots

Extended Sizes

Twisted XWomen's Embroidered Moc Toe Driving Chukka Booties

Internet Exclusive
Extended Sizes

Twisted XMen's Chukka Driving Mocs

Extended Sizes

Twisted XMen's Chukka Driving Mocs

Internet Exclusive
Extended Sizes

Bed StuMen's Illiad Leather Chukka Boots

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 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)

Johnston & MurphyMens Calder Suede Chukka Boot

Internet Exclusive
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(7)

Twisted XMen's Chukka Driving 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)

SorelMen's Buxton Lite Lace Plus Waterproof Boots

Internet Exclusive
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)

DannerWomen's Inquire Chukka Waterproof Suede Hiking Boots

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)

Flag LTD.Boys' Freddie Nubuck Lace Up Boots (Toddler)

Dillard's Exclusive

ALIGNMen's Rivers Weatherproof Oiled Leather Flannel Lined Winter Boots

Internet Exclusive

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 Mix Knit Faux Fur Lined Booties

Internet Exclusive
Extended Sizes

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)

MinnetonkaKids' Suede Fringe Softsole Boots (Infant)

Internet Exclusive

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 Chukka Driving Mocs

Internet Exclusive
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)

MinnetonkaWomen's Torrey Suede Gingham Print Faux Fur Lined Booties

Internet Exclusive
Extended Sizes

Twisted XMen's Driving Moccasin Chukka Boots

Internet Exclusive
Extended Sizes

MinnetonkaKids' Suede Fringe Softsole 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)

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)

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)

MinnetonkaGirls' Front Strap Fringe Detail Bootie Crib Shoes (Infant)

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

Only size 8, 10.5 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)

MinnetonkaKids' Fringe Bootie Crib Shoes (Infant)

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 Harrison Leather Chukka Boots

Extended Sizes
Rated 4.7059 out of 5 starsRated 4.7059 out of 5 starsRated 4.7059 out of 5 starsRated 4.7059 out of 5 starsRated 4.7059 out of 5 stars(34)

Twisted XWomen's Tooled Turquoise Stud Driving Moc Toe Chukka Boots

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(5)

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)

MinnetonkaKids' Braid Bootie Crib Shoes (Infant)

Twisted XMen's Moc Toe Leather 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(3)

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)

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(9)

MinnetonkaKids' Suede Fringe Softsole Boots (Youth)

Internet Exclusive
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)

BirkenstockMen's Utti Lace Up Chukkas

Permanently Reduced
Orig.
Now
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(6)

Johnston & MurphyMen's Upton 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)

BornMen's Ethan Distressed Suede Boots

Permanently Reduced
Orig.
Now
Extended Sizes

Cole HaanMen's Muir Leather Moc Toe Boots

Permanently Reduced
Orig.
Now
Internet Exclusive
Only size 9, 9.5 available

SorelMen's Slabtown 62' Stoic Suede 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(2)

Gentle SoulsCacti Suede Ankle Booties

Permanently Reduced
Orig.
Now
Extended Sizes
Only size 7, 9 available

Cole HaanMen's Muir Waterproof Suede Moc Toe Boots

Permanently Reduced
Orig.
Now
Internet Exclusive
Only size 9, 9.5 available

Johnston & MurphyMen's Braxton Oiled Leather Chukka Boots

Permanently Reduced
Orig.
Now
Internet Exclusive
Extended Sizes
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(2)

Cole HaanMen's Morse Leather Chukka Boots

Permanently Reduced
Orig.
Now
Internet Exclusive

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

Permanently Reduced
Orig.
Now
Extended Sizes
Rated 4.4615 out of 5 starsRated 4.4615 out of 5 starsRated 4.4615 out of 5 starsRated 4.4615 out of 5 starsRated 4.4615 out of 5 stars(13)

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

Permanently Reduced
Orig.
Now

Johnston & MurphyBoys' McGuffey Leather Lace Up Chukka Boots (Youth)

Permanently Reduced
Orig.
Now
Rated 4.9375 out of 5 starsRated 4.9375 out of 5 starsRated 4.9375 out of 5 starsRated 4.9375 out of 5 starsRated 4.9375 out of 5 stars(16)

TimberlandMen's Redwood Edge Leather Lace Up 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)

SorelMen's Slabtown 62 Moc Waterproof Boots

Permanently Reduced
Orig.
Now
Internet Exclusive
Extended Sizes
Only size 7 available
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)

SASKich Nubuck Lace Up Ankle Wedge Booties

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(1)

To Boot New YorkMen's Vista Chukka Boots

Permanently Reduced
Orig.
Now
Internet Exclusive
Extended Sizes
Only size 8.5 available

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

Permanently Reduced
Orig.
Now
Internet Exclusive
Only size 8.5, 12 available
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(11)

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

Permanently Reduced
Orig.
Now
Dillard's Exclusive

SorelMen's Madson II Waterproof Leather Chukka Boots

Permanently Reduced
Orig.
Now
Internet Exclusive
Extended Sizes
Only size 7, 7.5 available
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)

SorelMen's Cyprus Waterproof Leather 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(2)
Johnston & Murphy Boys' Calder Leather Hook-and-Loop Chukka Boots (Infant)Boys' Calder Leather Hook-and-Loop Chukka Boots (Infant)

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

Permanently Reduced
Orig.
Now
  • 96 Items

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