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8.5 : Medium Men's Casual Boots

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  • 208 Items
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Cole Haan Men's Chamberlin Water Resistant Nubuck Chelsea BootsMen's Chamberlin Water Resistant Nubuck Chelsea Boots

Cole HaanMen's Chamberlin Water Resistant Nubuck Chelsea Boots

Internet Exclusive
Timberland Men's Newmarket Chukka Leather BootsMen's Newmarket Chukka Leather Boots

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)
Steve Madden Men's Brompton Suede Chelsea BootsMen's Brompton Suede Chelsea Boots

Steve MaddenMen's Brompton Suede Chelsea Boots

Johnston & Murphy Men's XC+Durham Waterproof Leather Chelsea BootsMen's XC+Durham Waterproof Leather Chelsea Boots

Johnston & MurphyMen's XC+Durham Waterproof Leather Chelsea 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)
Johnston & Murphy Collection Men's Hartford Leather Plain Toe BootsCollection Men's Hartford Leather Plain Toe Boots

Johnston & MurphyCollection Men's Hartford Leather Plain Toe Boots

Rated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 stars(1)
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)
Dan Post Men's Ka Western BootsMen's Ka Western Boots

Dan PostMen's Ka Western Boots

Internet Exclusive
Extended Sizes
Rated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 stars(2)
Johnston & Murphy Mens Barrett Suede Zip BootsMens Barrett Suede Zip Boots

Johnston & MurphyMens Barrett Suede Zip Boots

Extended Sizes
Rated 2 out of 5 starsRated 2 out of 5 starsRated 2 out of 5 starsRated 2 out of 5 starsRated 2 out of 5 stars(1)
Men's Chamberlin Water Resistant Nubuck Chelsea Boots

PLACEHOLDERMen's Chamberlin Water Resistant Nubuck Chelsea Boots

Internet Exclusive

FryeMen's Austin Oiled Suede Inside Zip Western Boots

Internet Exclusive
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(18)

To Boot New YorkMen's Largo Chelsea Boots

Internet Exclusive

PLACEHOLDERMen's Chamberlin Water Resistant Nubuck Chelsea Boots

Internet Exclusive

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)

Steve MaddenMen's Daviston Lace Up Leather Chukka Boots

Internet Exclusive
Extended Sizes

PLACEHOLDERMen's Chamberlin Water Resistant Nubuck Chelsea Boots

Internet Exclusive

TimberlandMen's Redwood Falls Waterproof Leather Chukka Boots

Internet Exclusive
Extended Sizes
Rated 4.3167 out of 5 starsRated 4.3167 out of 5 starsRated 4.3167 out of 5 starsRated 4.3167 out of 5 starsRated 4.3167 out of 5 stars(60)

FryeMen's Engineer 12R Leather Buckle Hardware Boots

Internet Exclusive
Extended Sizes
Rated 4.1333 out of 5 starsRated 4.1333 out of 5 starsRated 4.1333 out of 5 starsRated 4.1333 out of 5 starsRated 4.1333 out of 5 stars(45)

PLACEHOLDERMen's Chamberlin Water Resistant Nubuck Chelsea Boots

Internet Exclusive

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

Internet Exclusive
Extended Sizes

Dan PostMen's Triton 13" Leather Snip Toe Western Boots

Internet Exclusive

DannerMen's Bull Run Leather 6" Chelsea Boots

Extended Sizes

Justin BootsMen's Moseley 11" Full Quill Ostrich Western Boots

Internet Exclusive

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)

Bruno MagliMen's Raging Leather Boots

Internet Exclusive

Bed StuMen's Protege Distressed Leather Back Zip Combat Boots

Internet Exclusive
Extended Sizes

FryeMen's Leather 12R O-Ring Harness Hardware Square Toe Boots

Rated 4.5125 out of 5 starsRated 4.5125 out of 5 starsRated 4.5125 out of 5 starsRated 4.5125 out of 5 starsRated 4.5125 out of 5 stars(80)

FryeMen's Duke Western Roper Leather Boots

Extended Sizes
Rated 3.6216 out of 5 starsRated 3.6216 out of 5 starsRated 3.6216 out of 5 starsRated 3.6216 out of 5 starsRated 3.6216 out of 5 stars(37)

ALIGNMen's Rangley Suede Chelsea Boots

Internet Exclusive

AriatMen's Classic Cash Wide Square Toe Western Boots

Rated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 stars(4)

FryeMen's Austin Leather Western Boots

Rated 2.75 out of 5 starsRated 2.75 out of 5 starsRated 2.75 out of 5 starsRated 2.75 out of 5 starsRated 2.75 out of 5 stars(8)

SorelMen's Scout 87' XT Waterproof Insulated Winter Boots

Internet Exclusive
Extended Sizes
Rated 3 out of 5 starsRated 3 out of 5 starsRated 3 out of 5 starsRated 3 out of 5 starsRated 3 out of 5 stars(5)

SorelMen's Carson Storm Waterproof Boots

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)

Justin BootsJustin Men's Poston 11" Western Boots

Internet Exclusive

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

Internet Exclusive

FryeMen's Hudson Suede Chelsea Work Boots

Internet Exclusive
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)

Steve MaddenMen's Harros Leather Chukka Boots

Rated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 stars(2)

Dan PostMen's Sturgis 13" Python Snake Leather Western Boots

Internet Exclusive

FryeMen's Landon Leather Midlace Cap Toe Boots

Internet Exclusive
Rated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 stars(1)

AriatMen's Plano Western Boots

Internet Exclusive
Rated 3.9412 out of 5 starsRated 3.9412 out of 5 starsRated 3.9412 out of 5 starsRated 3.9412 out of 5 starsRated 3.9412 out of 5 stars(17)

Justin BootsMen's Tobias 12" Leather Western Boots

ALIGNMen's Rangley Leather Chelsea Boots

Internet Exclusive

Dan PostMen's Bayou 13" Caiman Square Toe Western Boots

Internet Exclusive

Dan PostMen's Abram Western Boots

Extended Sizes

Tony LamaMen's Lenado 12" Western Boots

Extended Sizes

Tony LamaMen's Luciano 13" Western Boots

Internet Exclusive
Extended Sizes

Tony LamaMen's Amado 12" Suede Western Boots

Internet Exclusive
Extended Sizes

Justin BootsMen's Kilgore 10" Stampede Boots

Extended Sizes

Dan PostMen's Tempe 12" Full Quill Ostrich Western Boots

Internet Exclusive

Twisted XMen's Chukka Driving Moccasins

Internet Exclusive
Extended Sizes
Rated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 stars(1)

Tony LamaMen's Camarillo 13" Western Boots

Internet Exclusive
Extended Sizes

Johnston & MurphyCollection Men's Hartford Waxed Suede Chelsea Boots

ALIGNMen's Ryder Weatherproof Suede Boots

Internet Exclusive

Dan PostMen's Creed 12" Leather Square Toe Western Boots

Internet Exclusive

DannerMen's Logger Moc 917 GTX Waterproof Nubuck Leather Boots

Internet Exclusive
Extended Sizes

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

Internet Exclusive

TaftMen's Jack Wool Calfskin Cap Toe Braided Welt Detail Boots

Internet Exclusive
Extended Sizes
Rated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 stars(7)

Dan PostMen's Makara 13" Caiman Round Toe Western Boots

ALIGNMen's Rivers Weatherproof Oiled Leather Flannel Lined Winter Boots

Internet Exclusive

FryeMen's Paul Leather Cap Toe Lace Up Boots

Rated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 stars(1)

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

Extended Sizes

Dan PostMen's Wade 13" Leather Square Toe Western Boots

Internet Exclusive

FryeMen's Connor Suede Chelsea Boots

Internet Exclusive

FryeMen's Connor Waxed Suede Chelsea Boots

Internet Exclusive

Johnston & MurphyCollection Men's Flynch Suede Chelsea Boots

Internet Exclusive
Extended Sizes

Dan PostMen's Winslow 11" Leather Western Boots

Internet Exclusive
Extended Sizes

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

Internet Exclusive

AriatMen's Stoney Creek Distressed Leather Western Boots

Internet Exclusive

Justin BootsMen's Alamo 11" Roughout Boots

Internet Exclusive
Extended Sizes

TaftMen's Rome Bottega Suede Cap Toe Boots

Internet Exclusive

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

Internet Exclusive
Extended Sizes

Dan PostMen's Journeyman 11" Waterproof Leather Round Toe Work Boots

Internet Exclusive
Extended Sizes

Justin BootsMen's Fergus 11" Roughout Boots

Internet Exclusive
Extended Sizes

FryeMen's Barrett Leather Lace Up Boots

Internet Exclusive
Rated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 stars(1)

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

Internet Exclusive
Extended Sizes

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

Internet Exclusive
Extended Sizes

Justin BootsMen's Jackpot 11" Pull On Western Boots

Internet Exclusive

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

Internet Exclusive
Extended Sizes

Dan PostMen's Journeyman 11" Waterproof Leather Round Composite 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 Chukka Lug Suede Boots

Permanently Reduced
Orig.
Now
Extended Sizes

Polo Ralph LaurenMen's Ranger Suede and Twill Patch Detail Boots

Permanently Reduced
Orig.
Now
Extended Sizes
Rated 3 out of 5 starsRated 3 out of 5 starsRated 3 out of 5 starsRated 3 out of 5 starsRated 3 out of 5 stars(4)

Steve MaddenMen's Hatford Leather Chelsea Boots

Permanently Reduced
Orig.
Now
Extended Sizes

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)

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 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 stars(2)

Steve MaddenMen's Jotting Leather Contrast Stitch Cap Toe Boots

Permanently Reduced
Orig.
Now
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)

Steve MaddenMen's Tabriz Lace Up Leather Chukka Boots

Permanently Reduced
Orig.
Now
Extended Sizes

Johnston & MurphyMen's Upton Leather Chukka Boots

Permanently Reduced
Orig.
Now
Extended Sizes

Flag LTD.Men's Garrett Leather Plain Toe Boots

Permanently Reduced
Orig.
Now
Dillard's Exclusive
Rated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 stars(1)

Flag LTD.Men's Garrett Leather Chelsea Dress Boots

Permanently Reduced
Orig.
Now
Dillard's Exclusive

Johnston & MurphyMen's Barret Leather Plain Toe Boots

Permanently Reduced
Orig.
Now
Extended Sizes
Rated 4 out of 5 starsRated 4 out of 5 starsRated 4 out of 5 starsRated 4 out of 5 starsRated 4 out of 5 stars(6)

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)

Steve MaddenMen's Montreux Leather Chelsea Boots

Permanently Reduced
Orig.
Now
Extended Sizes
Rated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 stars(1)

BornMen's Brock Distressed Suede Boots

Permanently Reduced
Orig.
Now
Extended Sizes
Rated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 stars(9)

BornMen's Reed Leather Boots

Permanently Reduced
Orig.
Now
Extended Sizes

Polo Ralph LaurenMen's Ranger Suede Patch Detail Boots

Permanently Reduced
Orig.
Now
Internet Exclusive
Rated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 stars(1)

Section XMen's Steven Zip Suede Chelsea Boots

Permanently Reduced
Orig.
Now

Polo Ralph LaurenMen's Asher Suede Chukka Boots

Permanently Reduced
Orig.
Now
Twisted X Men's Leather Lace-Up Chukka Driving MoccasinsMen's Leather Lace-Up Chukka Driving Moccasins

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)
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