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Today's trends »
Men Shoes Chukka Boots
Sort By:
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Timberland Men's Redwood Falls Chukka Saddle Leather Waterproof Boots
NWT
$159
$220
Size: Various
Timberland
maxsr300
2
Kenneth Cole Reaction Grey Suede Boots, Men’s Size 13M
$38
$85
Size: 13
Kenneth Cole Reaction
goldiamglam
1
CLARKS SHACRE II STEP navy Quilted Casual Shoes
$30
$80
Size: 9
Clarks
dickersonsarah4
1
Clarks Quilted Black Casual Shoes
$30
$80
Size: 9
Clarks
dickersonsarah4
2
Converse Chuck Taylor All Star Outsider Boots Men's 10 Brown Textile Chunky Lug
$43
Size: 10
Converse
sabbypants2
2
Jcrew Desert Booties
$14
$95
Size: 9.5
J. Crew
beauty_sessie
1
UGG Australia 5548 Leather Chukka Cap Toe Boots Men’s 7.5 Black
$46
Size: 7.5
UGG
cherryyy_8
Cole Haan Original Grand Chukka Boots Waterproof Leather Brown Mens 8.5
$40
Size: 8.5
Cole Haan
galloping_horse
3
BLUNDSTONE Super 550 Chelsea Boot Premium Black Leather Pull-On
NWT
$189
$230
Size: 9.5
Blundstone
agogovintage
1
Clark’s black leather dress shoes,classic Black Chukka boot men’s 9 1/2 
$58
Size: 9.5
Clarks
adealwtd
1
Quoddy Men’s 9 Brown Leather Telos Chukka Capetian Trail Ankle Boots
$139
Size: 9
Quoddy
pinetreeresale
4
Diesel Bellow Black Suede Lace Up Chukka Men's Boots
$49
Size: 12.5
Diesel
dehbiand
Clarks Brown Chukka Boots with Suede Finish
NWT
$150
$250
Size: 9.5
Clarks
melendezayda403
Penny Luck Mens Chuka Boot Sz 9 Lace Up 100% Leather Stitched Cap Toe Brown EUC
$174
$349
Size: 9
Penny Luck
nbastian730007
3
Toms Mateo Lace-up Plaid Chukka Boot - Size 9
$45
Size: 9
Toms
dgrider8
NWOT Madewell Men's Olive Suede Chukka Boots Size 9.5
$55
Size: 9.5
Madewell
lovelytorii217
1
Florsheim Men's Black Leather Castellano Plain Toe Chukka Boot Size 9.5D
$57
$100,000
Size: 9.5
Florsheim
gjetson1
Adam Derrick Men's Olive Suede Chukka Boots Size 7.5
NWT
$100
$495
Size: 7.5
To Boot New York Adam Derrick
tmdesignerbrand
Dr Martens Bonny Black Chukka Lace Up Boots, Men’s Size 13
$79
Size: 13
Dr. Martens
kandice_cruz
6
Rockport XCS Mens Umbwe II Chukka Boots Vibram Waterproof Moc Toe 11.5 W New
$124
Size: 11.5
Rockport
javanaaa
3
Timberland Comfort Casual Men 9.5 Leather Lace Up Black Chunky Sole Shoes 79581
$30
Size: 9.5
Timberland
reshelleoldham
Heschung Boots Mens Brown Leather Manioc Buckle Chukka 10 US / 8.5 UK / 43 EU
$107
Size: 10
Heschung
harlow_james948
Koolaburra by UGG Asaiah Chukka Boot, Men's 9 - Like New!
$40
$100
Size: 9
Koolaburra
camarunde
Twisted X CHUKKA ULTRALITE X. Men’s size 13M
$60
Size: 13
Twisted X
lupitasmiel
11
Frye Men's Size 9 Chocolate Brown Chukka Leather Lace up Ankle Boots NEW
$110
Size: 9
Frye
amorashop2012
3
Reef Leucadian, tan
NWT
$50
$90
Size: 13
Reef
poshfoxcali
6
Gordon Rush Men's Size 9.5 Stafford Wingtip Distressed Leather Ankle Boot
$70
Size: 9.5
Gordon Rush
scottstechnical
Twisted X Men's High Top Brown Leather Shoes Moc Driving Boots Sz 9M
$55
Size: 9
Twisted X
alinanaranovich
Men’s WOLVERINE KARLIN Chukka Wheat Leather Work Boots, Size 9EW. Brand New!
NWT
$89
Size: 9
Wolverine
leachj974
9
2
MNY Marc New York Andrew Mark Shoes Mens 11 Ridge Three Eye Chukka Grey Suede
$30
Size: 11
Marc New York
shawnaejack1993
Clarks Bushacre 2 Brown Leather Beeswax Ankle Chukka Casual Boots Size 12
NWT
$80
$150
Size: 12
Clarks
bunny888
1
NIB $275 DEL TORO ALTO SUNBRELLA LEATHER DOT HIGH TOP CHUKKA SNEAKER US SIZE 17
NWT
$150
$275
Size: 17
Del Toro
hannahjack3
1
1
Red Wing IRISH SETTER 3873 Size 8.5 Soft Paw Chukka Hunting Boots gore Tex
$69
Size: 8.5
Red Wing Shoes
drewfreedman13
Polo Ralph Lauren Men's Keaton Suede Lace-Up Sneakers Size 7.5
NWT
$85
Size: 7.5
Polo by Ralph Lauren
ipereverzieva
Baffin Women’s Boots Size mens 7 Womens 9 Oxfords Waterproof Lace Up
$23
$149
Size: 7
Baffin
akdooley
Cole Haan Grand+ Plus Chukka Boots Casual Comfort Nubuck Leather Black Mens 12
$35
Size: 12
Cole Haan
galloping_horse
Brooks Brothers Mens Blue Suede Chukka Lace ups Size 8
$58
$208
Size: 10
Brooks Brothers
jenbennett436
United Nude Flx Desert Men's Suede Desert Chukka Boots Grey Size EU 45/US 11.5
$39
Size: 11.5
United Nude
romanri_83
2
UGG Neumel Pumice Suede Sheepskin Chukka Ankle Boots Shoes Size US 7 Men
$50
$119
Size: 7
UGG
metimm13
Peter Millar Chukka Suede Tan Lace Up Boots Size 11 M
$49
Size: 11
Peter Millar
hellokittymosa
4
Red Wing 3150 Mens Sz 12D Chukka Charcoal Work Shoe Mid Boot Solid Winter
$150
$349
Size: 12
Red Wing Shoes
scottstechnical
7
BEN Sherman Men’s Gray Lace Up Formal Casual Chukka Ankle Boots Shoes Size 12
$50
Size: 12
Ben Sherman
glambella2020
Ben Sherman Men's Nu Casual Chukka Boot Size 9
$12
$68
Size: 9
Ben Sherman
bohoali
Salvatore Ferragamo Italy Chukka Boots Leather Mens Shoes Rubber Soles Sz 8.5 EE
$100
$927
Size: 8.5 EE
Salvatore Ferragamo
mari2it
Chaco Boot Men 9.5 Black Dixon High Casual Ankle Snowplow Leather Lined
$45
Size: 9.5
Chaco
dress2thenine
1
Tommy Hilfiger gervis navy blue suede Chukka boots 10.5
$40
$150
Size: 10.5
Tommy Hilfiger
deltablue473
NWOT BONAFINI SHOES - CASUAL BOOTS Black Leather/Fabric For Men’s Size 6
$29
Size: 6
BONAFINI
gprokofeva
John Varvatos Star USA Men's Boots Size 9.5 M Brown Suede Lace Up Chukka Boots
$49
Size: 9.5
John Varvatos
vintagevince
2
2
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