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  • 205 Items
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L.L.Bean Men's Portland Leather Chelsea BootsMen's Portland Leather Chelsea Boots

L.L.BeanMen's Portland Leather Chelsea Boots

Rated 4.25 out of 5 starsRated 4.25 out of 5 starsRated 4.25 out of 5 starsRated 4.25 out of 5 starsRated 4.25 out of 5 stars(24)
Marc Nolan Men's Dax Cow Print Pony Hair Chelsea BootsMen's Dax Cow Print Pony Hair Chelsea Boots

Marc NolanMen's Dax Cow Print Pony Hair Chelsea Boots

Internet Exclusive
Extended Sizes
Ariat Men's Lookout Leather Chukka BootsMen's Lookout Leather Chukka Boots

AriatMen's Lookout Leather Chukka Boots

Only size 11 available
Rated 4.1159 out of 5 starsRated 4.1159 out of 5 starsRated 4.1159 out of 5 starsRated 4.1159 out of 5 starsRated 4.1159 out of 5 stars(69)
Danner Men's Logger Moc 917 GTX Waterproof Nubuck Leather BootsMen's Logger Moc 917 GTX Waterproof Nubuck Leather Boots

DannerMen's Logger Moc 917 GTX Waterproof Nubuck Leather Boots

Internet Exclusive
Extended Sizes
Frye Men's Paul Leather Zip BootsMen's Paul Leather Zip Boots

FryeMen's Paul Leather Zip Boots

Internet Exclusive
Rated 4.1667 out of 5 starsRated 4.1667 out of 5 starsRated 4.1667 out of 5 starsRated 4.1667 out of 5 starsRated 4.1667 out of 5 stars(6)
Steve Madden Men's Highline Suede Chelsea BootsMen's Highline Suede Chelsea Boots

Steve MaddenMen's Highline Suede Chelsea Boots

Internet Exclusive
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(5)
Cole Haan Men's ØriginalGrand CitySpectre Leather Chelsea BootsMen's ØriginalGrand CitySpectre Leather Chelsea Boots

Cole HaanMen's ØriginalGrand CitySpectre Leather Chelsea Boots

Internet Exclusive
Pikolinos Men's Vigo Leather Lace Up Zip Ankle BootsMen's Vigo Leather Lace Up Zip Ankle Boots

PikolinosMen's Vigo Leather Lace Up Zip Ankle Boots

Men's Portland Leather Chelsea Boots

PLACEHOLDERMen's Portland Leather Chelsea Boots

Rated 4.25 out of 5 starsRated 4.25 out of 5 starsRated 4.25 out of 5 starsRated 4.25 out of 5 starsRated 4.25 out of 5 stars(24)

SorelMen's CYPRUS Waterproof Suede Chelsea Boots

Extended Sizes

Marc NolanMen's Dante Cow Print Boots

Extended Sizes

PLACEHOLDERMen's Portland Leather Chelsea Boots

Rated 4.25 out of 5 starsRated 4.25 out of 5 starsRated 4.25 out of 5 starsRated 4.25 out of 5 starsRated 4.25 out of 5 stars(24)

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)

FryeTyler Flex Leather Chelsea Boots

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(4)

PLACEHOLDERMen's Portland Leather Chelsea Boots

Rated 4.25 out of 5 starsRated 4.25 out of 5 starsRated 4.25 out of 5 starsRated 4.25 out of 5 starsRated 4.25 out of 5 stars(24)

ALIGNMen's Eddy Waterproof Leather Lace Up Boots

AriatMen's Wexford Waterproof Chelsea Boots

Rated 4.5294 out of 5 starsRated 4.5294 out of 5 starsRated 4.5294 out of 5 starsRated 4.5294 out of 5 starsRated 4.5294 out of 5 stars(255)

PLACEHOLDERMen's Portland Leather Chelsea Boots

Rated 4.25 out of 5 starsRated 4.25 out of 5 starsRated 4.25 out of 5 starsRated 4.25 out of 5 starsRated 4.25 out of 5 stars(24)

Twisted XMen's Chukka Driving Mocs

Internet Exclusive
Extended Sizes

Dan PostMen's Ka Western 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)

Dan PostMen's Kingsly 11" Caiman Square Toe Western Boots

Extended Sizes

Bed StuMen's Protege Distressed Leather Back Zip Combat Boots

Internet Exclusive
Extended Sizes

Bruno MagliMen's Raging Leather Boots

Internet Exclusive
Only size 8.5, 13 available

Dune LondonMen's Smoky Leather Casual Ankle Boots

Internet Exclusive

ALIGNMen's Rangley Leather Chelsea Boots

Dan PostMen's Brutus 11" Python Snake Square Toe Western Boots

Internet Exclusive

Johnston & MurphyMen's XC+Durham Waterproof Suede Chelsea 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)

TaftMen's Jack Wool Cap Toe Boots

Internet Exclusive
Rated 4.8661 out of 5 starsRated 4.8661 out of 5 starsRated 4.8661 out of 5 starsRated 4.8661 out of 5 starsRated 4.8661 out of 5 stars(1195)

AriatMen's Heritage Roper Western Boots

Internet Exclusive
Extended Sizes
Rated 4.4586 out of 5 starsRated 4.4586 out of 5 starsRated 4.4586 out of 5 starsRated 4.4586 out of 5 starsRated 4.4586 out of 5 stars(290)

ALDOMen's Walton Leather Lace Up Booties

Internet Exclusive
Extended Sizes

ALIGNMen's Ryder Weatherproof Suede Boots

Internet Exclusive

ALIGNMen's Rangley Suede Chelsea Boots

Johnston & MurphyCollection Men's Hartford Suede Plain Toe Boots

Internet Exclusive

ALDOMen's Farrell Leather Lace Up Boots

Extended Sizes

Bed StuMen's Michelangelo Rustic Leather Chelsea Boots

Internet Exclusive

Dan PostMen's Abram Western Boots

Internet Exclusive
Extended Sizes

ALDOMen's Zeddy Suede Chelsea Boots

Internet Exclusive
Extended Sizes

Dune LondonMen's Call Leather Cap Toe Zip Buckle Hardware 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)

ALIGNMen's Rivers Weatherproof Oiled Leather Flannel Lined Winter Boots

Internet Exclusive

Twisted XMen's Slip-On Chukka Leather Driving Moccasin 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)

Dune LondonMen's Matias Leather Ankle Boots

Internet Exclusive

Dan PostMen's Cottonwood 13" Leather Round Toe Western Boots

Internet Exclusive

Dan PostMen's Winslow 11" Leather Western Boots

Internet Exclusive
Extended Sizes

AriatMen's Bomber Rambler Recon Western Boots

Internet Exclusive
Only size 11.5 available
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(148)

Dan PostMen's Alamosa 11" Full Quill Ostrich Square Toe Western Boots

Internet Exclusive
Extended Sizes

Dune LondonMen's Saltwood Leather Cap Toe Chelsea Boots

Internet Exclusive

Dan PostMen's Murray 11" Bison Leather Square Toe Western Boots

Internet Exclusive

DingoMen's Road Trip Suede O-Ring Harness Hardware Lug Sole Boots

Internet Exclusive
Extended Sizes

AriatMen's Plano Western Boots

Internet Exclusive
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(18)

Johnston & MurphyCollection Men's Flynch Suede Chelsea Boots

Internet Exclusive
Extended Sizes

Dan PostMen's Storms Eye 11" Waterproof Leather Composite Toe Work Boots

Internet Exclusive
Extended Sizes
Only size 9, 14 available

Dan PostMen's Sire 11" Waterproof Leather Steel Toe Work Boots

Internet Exclusive
Extended Sizes
Only size 12 available

Dan PostMen's Tumbleweed 11" Waterproof Leather Steel Toe Work Boots

Internet Exclusive
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)

UGGMen's Classic Suede Family Matching Short 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(6)

Johnston & MurphyMen's XC Flex Raleigh Leather Chelsea Boots

Permanently Reduced
Orig.
Now
Extended Sizes
Rated 4.6842 out of 5 starsRated 4.6842 out of 5 starsRated 4.6842 out of 5 starsRated 4.6842 out of 5 starsRated 4.6842 out of 5 stars(57)

UGGMen's Classic Mini GTX Boots

Permanently Reduced
Orig.
Now
Extended Sizes

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

Permanently Reduced
Orig.
Now
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(5)

AriatMen's Barrett Leather Boots

Permanently Reduced
Orig.
Now
Extended Sizes
Only size 10.5, 11.5 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(4)

Flag LTD.Men's Garrett Leather Plain Toe Boots

Permanently Reduced
Orig.
Now
Dillard's 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)

BornMen's Reed Leather Boots

Permanently Reduced
Orig.
Now
Extended Sizes

BornMen's Ethan Distressed Suede Boots

Permanently Reduced
Orig.
Now
Extended Sizes

BornMen's Erik Leather Boots

Permanently Reduced
Orig.
Now
Extended Sizes

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

Permanently Reduced
Orig.
Now
Extended Sizes
Only size 8, 10 available

Johnston & MurphyMen's Upton Leather Chukka Boots

Permanently Reduced
Orig.
Now
Extended Sizes

Steve MaddenMen's Jotting Leather Contrast Stitch Cap Toe Boots

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

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

BirkenstockMen's Highwood Leather Chelsea Boots

Permanently Reduced
Orig.
Now

Johnston & MurphyMen's Upton Leather Chelsea Boots

Permanently Reduced
Orig.
Now
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(6)

Steve MaddenMen's Hatford Leather Chelsea 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)

COACHMen's Lug Sole Leather Boots

Permanently Reduced
Orig.
Now
Internet Exclusive
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)

Flag LTD.Men's Garrett Leather Chelsea Dress Boots

Permanently Reduced
Orig.
Now
Dillard's Exclusive

Flag LTD.Men's Marsen Cap Toe Leather Lace-Up Hiker Boots

Permanently Reduced
Orig.
Now
Dillard's Exclusive
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(17)

Steve MaddenMen's Hatford Suede Chelsea 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(3)

ALIGNMen's Rivers Weatherproof Tumbled Leather Boots

Permanently Reduced
Orig.
Now

UGGMen's Chelsea Lug 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(1)

Donald PlinerMen's Ashford Leather Chelsea Boots

Permanently Reduced
Orig.
Now
Internet Exclusive
Extended Sizes

Steve MaddenMen's Montreux Leather Chelsea 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 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 Calder 175th Anniversary Leather Chelsea Boots

Permanently Reduced
Orig.
Now
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(3)

UGGMen's Neumel High Weather Hybrid Lace Up Boots

Permanently Reduced
Orig.
Now
Extended Sizes

Kurt Geiger LondonMen's Chiltern Leather Boots

Permanently Reduced
Orig.
Now

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

Permanently Reduced
Orig.
Now
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)

Johnston & MurphyMen's Barret Leather Plain Toe Boots

Permanently Reduced
Orig.
Now
Extended Sizes
Rated 4.1429 out of 5 starsRated 4.1429 out of 5 starsRated 4.1429 out of 5 starsRated 4.1429 out of 5 starsRated 4.1429 out of 5 stars(7)

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)

TimberlandMen's Redwood Falls Waterproof Leather Chukka Boots

Permanently Reduced
Orig.
Now
Internet Exclusive
Extended Sizes
Only size 11.5 available
Rated 4.3768 out of 5 starsRated 4.3768 out of 5 starsRated 4.3768 out of 5 starsRated 4.3768 out of 5 starsRated 4.3768 out of 5 stars(69)

UGGMen's Lug Chukka Boots

Permanently Reduced
Orig.
Now
Internet Exclusive
Extended Sizes
Only size 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(1)

Section XMen's Steven Zip Suede Chelsea Boots

Permanently Reduced
Orig.
Now
Dillard's Exclusive

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)

Johnston & MurphyMen's Barret Suede Plain Toe Boots

Permanently Reduced
Orig.
Now
Internet Exclusive
Extended Sizes
Rated 3.75 out of 5 starsRated 3.75 out of 5 starsRated 3.75 out of 5 starsRated 3.75 out of 5 starsRated 3.75 out of 5 stars(8)

Cole HaanMen's Chamberlin Water Resistant Nubuck Cap Toe Boots

Permanently Reduced
Orig.
Now
Internet Exclusive

Steve MaddenMen's Walvia Nubuck Lug Sole Work Boots

Permanently Reduced
Orig.
Now
Extended Sizes

Steve MaddenMen's Aben Leather Chelsea Boots

Permanently Reduced
Orig.
Now

Polo Ralph LaurenMen's Asher Suede Chukka Boots

Permanently Reduced
Orig.
Now
Only size 8.5, 11 available

Cole HaanMen's American Classics Plain Toe Waterproof Boots

Permanently Reduced
Orig.
Now
Internet Exclusive
Rated 4.4118 out of 5 starsRated 4.4118 out of 5 starsRated 4.4118 out of 5 starsRated 4.4118 out of 5 starsRated 4.4118 out of 5 stars(34)

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

Permanently Reduced
Orig.
Now
Rated 3.8571 out of 5 starsRated 3.8571 out of 5 starsRated 3.8571 out of 5 starsRated 3.8571 out of 5 starsRated 3.8571 out of 5 stars(7)

EastlandMen's Ethan 1955 Leather Boots

Permanently Reduced
Orig.
Now
Internet Exclusive
Extended Sizes
Only size 9 available
Steve Madden Men's Tabriz Lace Up Leather Chukka BootsMen's Tabriz Lace Up Leather Chukka Boots

Steve MaddenMen's Tabriz Lace Up Leather Chukka Boots

Permanently Reduced
Orig.
Now
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)
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