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Born
Men's Hemlock Leather Chelsea Boots
Extended Sizes
Rated 4.62 out of 5 stars
Rated 4.62 out of 5 stars
Rated 4.62 out of 5 stars
Rated 4.62 out of 5 stars
Rated 4.62 out of 5 stars
(34)
Johnston & Murphy
Men's Upton Chukka Boots
Extended Sizes
Rated 4.62 out of 5 stars
Rated 4.62 out of 5 stars
Rated 4.62 out of 5 stars
Rated 4.62 out of 5 stars
Rated 4.62 out of 5 stars
(125)
Magnanni
Men's Lastico Leather Boots
Extended Sizes
Rated 5.0 out of 5 stars
Rated 5.0 out of 5 stars
Rated 5.0 out of 5 stars
Rated 5.0 out of 5 stars
Rated 5.0 out of 5 stars
(1)
Timberland
Men's Earthkeeper Leather Boots
Extended Sizes
Rated 4.34 out of 5 stars
Rated 4.34 out of 5 stars
Rated 4.34 out of 5 stars
Rated 4.34 out of 5 stars
Rated 4.34 out of 5 stars
(756)
Josef Seibel
Men's Earl 04 Leather Lace-Up Chukka Boots
Extended Sizes
Rated 5.0 out of 5 stars
Rated 5.0 out of 5 stars
Rated 5.0 out of 5 stars
Rated 5.0 out of 5 stars
Rated 5.0 out of 5 stars
(5)
Timberland
Men's 6-Inch Premium Waterproof Cold Weather Boots
Extended Sizes
Rated 4.44 out of 5 stars
Rated 4.44 out of 5 stars
Rated 4.44 out of 5 stars
Rated 4.44 out of 5 stars
Rated 4.44 out of 5 stars
(664)
Steve Madden
Men's Jotter Cap Toe Boots
Extended Sizes
Rated 4.86 out of 5 stars
Rated 4.86 out of 5 stars
Rated 4.86 out of 5 stars
Rated 4.86 out of 5 stars
Rated 4.86 out of 5 stars
(43)
Blundstone
Men's 550 Water-Resistant Chelsea Boots
Rated 4.7 out of 5 stars
Rated 4.7 out of 5 stars
Rated 4.7 out of 5 stars
Rated 4.7 out of 5 stars
Rated 4.7 out of 5 stars
(182)
Johnston & Murphy
Men's XC4 Stanton 2.0 Waterproof Chelsea Boots
Save on Select Items
Orig.
Now
Rated 4.5 out of 5 stars
Rated 4.5 out of 5 stars
Rated 4.5 out of 5 stars
Rated 4.5 out of 5 stars
Rated 4.5 out of 5 stars
(2)
Timberland
Men's Maple Grove Chukka Boots
Rated 4.56 out of 5 stars
Rated 4.56 out of 5 stars
Rated 4.56 out of 5 stars
Rated 4.56 out of 5 stars
Rated 4.56 out of 5 stars
(54)
Born
Men's Harrison Leather Chukka Boots
Extended Sizes
Rated 4.69 out of 5 stars
Rated 4.69 out of 5 stars
Rated 4.69 out of 5 stars
Rated 4.69 out of 5 stars
Rated 4.69 out of 5 stars
(32)
Polo Ralph Lauren
Men's Ranger Tumbled Leather Buckle Lug Sole Boots
Extended Sizes
Rated 4.56 out of 5 stars
Rated 4.56 out of 5 stars
Rated 4.56 out of 5 stars
Rated 4.56 out of 5 stars
Rated 4.56 out of 5 stars
(9)
Timberland
Men's Mt. Maddsen Waterproof Leather Boots
Extended Sizes
Rated 4.59 out of 5 stars
Rated 4.59 out of 5 stars
Rated 4.59 out of 5 stars
Rated 4.59 out of 5 stars
Rated 4.59 out of 5 stars
(1222)
Ariat
Men's Booker Ultra Western Boots
Extended Sizes
Rated 4.8 out of 5 stars
Rated 4.8 out of 5 stars
Rated 4.8 out of 5 stars
Rated 4.8 out of 5 stars
Rated 4.8 out of 5 stars
(502)
Ariat
Men's Booker Ultra Western Leather Boots
Extended Sizes
Rated 4.8 out of 5 stars
Rated 4.8 out of 5 stars
Rated 4.8 out of 5 stars
Rated 4.8 out of 5 stars
Rated 4.8 out of 5 stars
(502)
Eastland
Men's Lumber Up Work Boots
Extended Sizes
Rated 1.0 out of 5 stars
Rated 1.0 out of 5 stars
Rated 1.0 out of 5 stars
Rated 1.0 out of 5 stars
Rated 1.0 out of 5 stars
(1)
UGG
Men's Burleigh Waterproof Cold Weather Chukka Boots
Extended Sizes
Rated 4.89 out of 5 stars
Rated 4.89 out of 5 stars
Rated 4.89 out of 5 stars
Rated 4.89 out of 5 stars
Rated 4.89 out of 5 stars
(9)
Steve Madden
Men's Harken Chukka Boots
Extended Sizes
Rated 4.68 out of 5 stars
Rated 4.68 out of 5 stars
Rated 4.68 out of 5 stars
Rated 4.68 out of 5 stars
Rated 4.68 out of 5 stars
(62)
Ariat
Men's Lookout Chukka Boots
Rated 4.11 out of 5 stars
Rated 4.11 out of 5 stars
Rated 4.11 out of 5 stars
Rated 4.11 out of 5 stars
Rated 4.11 out of 5 stars
(70)
Ariat
Men's Spitfire Waterproof Leather Boots
Extended Sizes
Rated 4.6 out of 5 stars
Rated 4.6 out of 5 stars
Rated 4.6 out of 5 stars
Rated 4.6 out of 5 stars
Rated 4.6 out of 5 stars
(30)
Twisted X
Men's Work 4" Steel Toe Leather Wedge Sole Boot
Extended Sizes
Born
Men's Brock Distressed Suede Boots
Extended Sizes
Rated 5.0 out of 5 stars
Rated 5.0 out of 5 stars
Rated 5.0 out of 5 stars
Rated 5.0 out of 5 stars
Rated 5.0 out of 5 stars
(6)
Timberland
Men's Maplegrove Chukka Boots
Extended Sizes
Rated 4.56 out of 5 stars
Rated 4.56 out of 5 stars
Rated 4.56 out of 5 stars
Rated 4.56 out of 5 stars
Rated 4.56 out of 5 stars
(54)
Ariat
Men's Rambler Chelsea Boots
Rated 4.45 out of 5 stars
Rated 4.45 out of 5 stars
Rated 4.45 out of 5 stars
Rated 4.45 out of 5 stars
Rated 4.45 out of 5 stars
(208)
Twisted X
Men's Waterproof Chukka Driving Moccasins
Extended Sizes
Rated 4.67 out of 5 stars
Rated 4.67 out of 5 stars
Rated 4.67 out of 5 stars
Rated 4.67 out of 5 stars
Rated 4.67 out of 5 stars
(3)
UGG
Men's Biltmore Waterproof Suede Cold Weather Chelsea Boots
Extended Sizes
Rated 4.75 out of 5 stars
Rated 4.75 out of 5 stars
Rated 4.75 out of 5 stars
Rated 4.75 out of 5 stars
Rated 4.75 out of 5 stars
(24)
Born
Men's Nigel Leather Lace-Up Boots
Extended Sizes
Rated 4.63 out of 5 stars
Rated 4.63 out of 5 stars
Rated 4.63 out of 5 stars
Rated 4.63 out of 5 stars
Rated 4.63 out of 5 stars
(16)
Merrell
Men's Moab Speed 2 Mid GORE-TEX Hikers
Extended Sizes
Rated 4.67 out of 5 stars
Rated 4.67 out of 5 stars
Rated 4.67 out of 5 stars
Rated 4.67 out of 5 stars
Rated 4.67 out of 5 stars
(27)
Twisted X
Men's Pull-On Moc Toe Leather Boots
Extended Sizes
Rated 5.0 out of 5 stars
Rated 5.0 out of 5 stars
Rated 5.0 out of 5 stars
Rated 5.0 out of 5 stars
Rated 5.0 out of 5 stars
(5)
Timberland
Men's Redwood Falls Waterproof Cold Weather Boots
Extended Sizes
Rated 4.56 out of 5 stars
Rated 4.56 out of 5 stars
Rated 4.56 out of 5 stars
Rated 4.56 out of 5 stars
Rated 4.56 out of 5 stars
(75)
Twisted X
Men's ECO Moc Toe Lace Up Boot
Rated 5.0 out of 5 stars
Rated 5.0 out of 5 stars
Rated 5.0 out of 5 stars
Rated 5.0 out of 5 stars
Rated 5.0 out of 5 stars
(2)
Polo Ralph Lauren
Men's Oslo Low Leather and Suede Waterproof Lug Sole Boots
Rated 4.67 out of 5 stars
Rated 4.67 out of 5 stars
Rated 4.67 out of 5 stars
Rated 4.67 out of 5 stars
Rated 4.67 out of 5 stars
(6)
Twisted X
Men's 4" Woven Leather Boots
Extended Sizes
Rated 5.0 out of 5 stars
Rated 5.0 out of 5 stars
Rated 5.0 out of 5 stars
Rated 5.0 out of 5 stars
Rated 5.0 out of 5 stars
(1)
Polo Ralph Lauren
Men's Oslo Buckled Detail Waterproof Cold Weather Boots
Internet Exclusive
Extended Sizes
Rated 5.0 out of 5 stars
Rated 5.0 out of 5 stars
Rated 5.0 out of 5 stars
Rated 5.0 out of 5 stars
Rated 5.0 out of 5 stars
(6)
Born
Men's Brody Destressed Leather Chelsea Boots
Extended Sizes
Rated 5.0 out of 5 stars
Rated 5.0 out of 5 stars
Rated 5.0 out of 5 stars
Rated 5.0 out of 5 stars
Rated 5.0 out of 5 stars
(19)
Timberland
Men's Mt. Maddsen Leather Boots
Rated 4.59 out of 5 stars
Rated 4.59 out of 5 stars
Rated 4.59 out of 5 stars
Rated 4.59 out of 5 stars
Rated 4.59 out of 5 stars
(1222)
Johnston & Murphy
Men's Upton Leather Lace-Up Chukka Boots
Extended Sizes
Rated 4.62 out of 5 stars
Rated 4.62 out of 5 stars
Rated 4.62 out of 5 stars
Rated 4.62 out of 5 stars
Rated 4.62 out of 5 stars
(125)
Timberland
Men's Redwood Falls Chelsea Boots
Extended Sizes
Rated 4.41 out of 5 stars
Rated 4.41 out of 5 stars
Rated 4.41 out of 5 stars
Rated 4.41 out of 5 stars
Rated 4.41 out of 5 stars
(106)
Ariat
Men's Hybrid Low Boy Boots
Rated 4.62 out of 5 stars
Rated 4.62 out of 5 stars
Rated 4.62 out of 5 stars
Rated 4.62 out of 5 stars
Rated 4.62 out of 5 stars
(63)
To Boot New York
Men's Leather Lace-Up Burkett Boots
Extended Sizes
Rated 5.0 out of 5 stars
Rated 5.0 out of 5 stars
Rated 5.0 out of 5 stars
Rated 5.0 out of 5 stars
Rated 5.0 out of 5 stars
(1)
Blundstone
Men's Water-Resistant Chelsea Boots
Polo Ralph Lauren
Men's Suede Ranger Boots
Internet Exclusive
Extended Sizes
Johnston & Murphy
Men's Barrett Moc Toe Boots
Internet Exclusive
Extended Sizes
Rated 4.28 out of 5 stars
Rated 4.28 out of 5 stars
Rated 4.28 out of 5 stars
Rated 4.28 out of 5 stars
Rated 4.28 out of 5 stars
(60)
Magnanni
Men's Lastico Suede Boots
Rated 5.0 out of 5 stars
Rated 5.0 out of 5 stars
Rated 5.0 out of 5 stars
Rated 5.0 out of 5 stars
Rated 5.0 out of 5 stars
(1)
Johnston & Murphy
Men's Upton Chelsea Boots
Extended Sizes
Rated 4.79 out of 5 stars
Rated 4.79 out of 5 stars
Rated 4.79 out of 5 stars
Rated 4.79 out of 5 stars
Rated 4.79 out of 5 stars
(156)
Magnanni
Men's Peyton III Boots
Internet Exclusive
Polo Ralph Lauren
Men's Oslo High II Boots
Internet Exclusive
Extended Sizes
L.L.Bean
Men's Access Mid Hiker Boots
Rated 4.75 out of 5 stars
Rated 4.75 out of 5 stars
Rated 4.75 out of 5 stars
Rated 4.75 out of 5 stars
Rated 4.75 out of 5 stars
(4)
Timberland
Men's Euro Hiker Boots
Internet Exclusive
Rated 4.6 out of 5 stars
Rated 4.6 out of 5 stars
Rated 4.6 out of 5 stars
Rated 4.6 out of 5 stars
Rated 4.6 out of 5 stars
(922)
UGG
Men's Burleigh Waterproof Lace-Up Winter Boots
Rated 4.43 out of 5 stars
Rated 4.43 out of 5 stars
Rated 4.43 out of 5 stars
Rated 4.43 out of 5 stars
Rated 4.43 out of 5 stars
(7)
Frye
Blk Paul Chelsea Leather Boots
Extended Sizes
Ariat
Men's Sport Wide Square Toe Colorblock Western Boots
Internet Exclusive
Extended Sizes
Rated 4.8 out of 5 stars
Rated 4.8 out of 5 stars
Rated 4.8 out of 5 stars
Rated 4.8 out of 5 stars
Rated 4.8 out of 5 stars
(124)
Timberland
Men's Arbor Road Waterproof 6" Boot
Extended Sizes
Rated 4.67 out of 5 stars
Rated 4.67 out of 5 stars
Rated 4.67 out of 5 stars
Rated 4.67 out of 5 stars
Rated 4.67 out of 5 stars
(24)
Timberland
Men's Redwood Falls Waterproof Leather Chukka Boots
Extended Sizes
Rated 4.57 out of 5 stars
Rated 4.57 out of 5 stars
Rated 4.57 out of 5 stars
Rated 4.57 out of 5 stars
Rated 4.57 out of 5 stars
(91)
Frye
Men's Astor Chukka Boots
Twisted X
Men's Leather Lace-Up Chukka Driving Moccasins
Extended Sizes
Rated 4.67 out of 5 stars
Rated 4.67 out of 5 stars
Rated 4.67 out of 5 stars
Rated 4.67 out of 5 stars
Rated 4.67 out of 5 stars
(3)
Danner
Men's Bull Run Two-Tone Lux Boots
Extended Sizes
Rated 5.0 out of 5 stars
Rated 5.0 out of 5 stars
Rated 5.0 out of 5 stars
Rated 5.0 out of 5 stars
Rated 5.0 out of 5 stars
(2)
Ariat
Men's Spitfire Boots
Extended Sizes
Rated 4.71 out of 5 stars
Rated 4.71 out of 5 stars
Rated 4.71 out of 5 stars
Rated 4.71 out of 5 stars
Rated 4.71 out of 5 stars
(248)
Twisted X
Men's Chukka Driving Moccasins
Extended Sizes
Rated 5.0 out of 5 stars
Rated 5.0 out of 5 stars
Rated 5.0 out of 5 stars
Rated 5.0 out of 5 stars
Rated 5.0 out of 5 stars
(1)
Pikolinos
Men's York Boots
Internet Exclusive
Eastland
Men's Daily Double Leather Chelsea Boots
Internet Exclusive
Extended Sizes
Rated 4.0 out of 5 stars
Rated 4.0 out of 5 stars
Rated 4.0 out of 5 stars
Rated 4.0 out of 5 stars
Rated 4.0 out of 5 stars
(1)
Merrell
Men's Speed Solo Mid Waterproof Suede Boots
Extended Sizes
Rated 3.71 out of 5 stars
Rated 3.71 out of 5 stars
Rated 3.71 out of 5 stars
Rated 3.71 out of 5 stars
Rated 3.71 out of 5 stars
(28)
Frye
Men's Astor Leather Chukka Boots
Extended Sizes
Frye
Men's Tyler Leather Chelsea Boots
Extended Sizes
L.L.Bean
Men's Wellie Sport Waterproof Chelsea Boots
Internet Exclusive
Rated 3.8 out of 5 stars
Rated 3.8 out of 5 stars
Rated 3.8 out of 5 stars
Rated 3.8 out of 5 stars
Rated 3.8 out of 5 stars
(20)
Twisted X
Men's Slip-On Chukka Leather Driving Moccasin Boots
Extended Sizes
Rated 5.0 out of 5 stars
Rated 5.0 out of 5 stars
Rated 5.0 out of 5 stars
Rated 5.0 out of 5 stars
Rated 5.0 out of 5 stars
(2)
Frye
Men's Engineer Buckle 12R Leather Boots
Extended Sizes
Dingo
Men's High Country Suede Lug Sole Boots
Internet Exclusive
Extended Sizes
Timberland
Men's Westmore Boots
Frye
Men's Tyler Lace-Up Classic Boots
Extended Sizes
Blundstone
Men's 550 Casual Slip-On Chelsea Boots
Extended Sizes
Rated 2.0 out of 5 stars
Rated 2.0 out of 5 stars
Rated 2.0 out of 5 stars
Rated 2.0 out of 5 stars
Rated 2.0 out of 5 stars
(1)
Frye
Men's Harness 12R Leather Boots
Internet Exclusive
Rated 3.67 out of 5 stars
Rated 3.67 out of 5 stars
Rated 3.67 out of 5 stars
Rated 3.67 out of 5 stars
Rated 3.67 out of 5 stars
(3)
Bed Stu
Men's Clyde Leather Chukka Boots
Internet Exclusive
Extended Sizes
Sorel
Men's Carson Storm Waterproof Boots
Rated 4.8 out of 5 stars
Rated 4.8 out of 5 stars
Rated 4.8 out of 5 stars
Rated 4.8 out of 5 stars
Rated 4.8 out of 5 stars
(20)
Sorel
Men's Carson Waterproof Cold Weather Chelsea Boots
Internet Exclusive
Extended Sizes
Rated 3.87 out of 5 stars
Rated 3.87 out of 5 stars
Rated 3.87 out of 5 stars
Rated 3.87 out of 5 stars
Rated 3.87 out of 5 stars
(39)
Merrell
Men's Nova 3 Thermo Waterproof Hiking Boots
Rated 4.5 out of 5 stars
Rated 4.5 out of 5 stars
Rated 4.5 out of 5 stars
Rated 4.5 out of 5 stars
Rated 4.5 out of 5 stars
(36)
Merrell
Men's Wildwood Mid Waterproof Boots
Internet Exclusive
Extended Sizes
Ariat
Men's Lookout Chukka Boots
Internet Exclusive
Rated 4.11 out of 5 stars
Rated 4.11 out of 5 stars
Rated 4.11 out of 5 stars
Rated 4.11 out of 5 stars
Rated 4.11 out of 5 stars
(70)
Chaco
Men's Revel Slip-On Chelsea Boots
Internet Exclusive
Extended Sizes
Rated 3.5 out of 5 stars
Rated 3.5 out of 5 stars
Rated 3.5 out of 5 stars
Rated 3.5 out of 5 stars
Rated 3.5 out of 5 stars
(2)
Bed Stu
Men's Lincoln Lace-Up Leather Boots
Internet Exclusive
UGG
Men's Burleigh Waterproof Chelsea Winter Boots
Rated 4.8 out of 5 stars
Rated 4.8 out of 5 stars
Rated 4.8 out of 5 stars
Rated 4.8 out of 5 stars
Rated 4.8 out of 5 stars
(5)
Frye
Men's Astor Leather Lace-Up Chukka Boots
Internet Exclusive
Extended Sizes
G.H. Bass
Men's Ranger Chelsea Boots
Extended Sizes
Frye
Men's Leather Hudson Chelsea Wedge Work Boots
Internet Exclusive
Extended Sizes
Bed Stu
Men's Protege Trek Leather Combat Boots
Frye
Men's Astor Suede Chukka Boots
Internet Exclusive
Extended Sizes
Frye
Men's Hudson Leather Wedge Work Boots
Internet Exclusive
Extended Sizes
Dingo
Men's Road Trip Harness Suede Lug Sole Boots
Extended Sizes
Eastland
Men's Herman Chelsea Boots
Internet Exclusive
Sorel
Men's Hi-Line Waterproof Cold Weather Chelsea Boots
Extended Sizes
Rated 4.6 out of 5 stars
Rated 4.6 out of 5 stars
Rated 4.6 out of 5 stars
Rated 4.6 out of 5 stars
Rated 4.6 out of 5 stars
(42)
Allen-Edmonds
Men's Harris Chukka Suede Boots
Internet Exclusive
Extended Sizes
Bed Stu
Men's Old Bowen Leather Zip Trek Boots
Internet Exclusive
Chaco
Men's Fields Lace Waterproof Boots
Internet Exclusive
Bed Stu
Men's Lincoln Leather Lace-Up Boots
Internet Exclusive
Allen-Edmonds
Men's Harris Chukka Leather Boots
Internet Exclusive
Extended Sizes
Eastland
Men's Seneca Leather Chukka Boots
Internet Exclusive
Extended Sizes
Rated 5.0 out of 5 stars
Rated 5.0 out of 5 stars
Rated 5.0 out of 5 stars
Rated 5.0 out of 5 stars
Rated 5.0 out of 5 stars
(2)
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