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Stetson Men's All-Over Suede Casual Lace-Up Chukka Boot Round Toe -

Stetson Men's All-Over Suede Casual Lace-Up Chukka Boot Round Toe -

$240.99$120.50

Men's Chukka Ankle Boots Casual Business Work Shoes for Men

Men's Chukka Ankle Boots Casual Business Work Shoes for Men

$81.00$40.50

Men's Handmade Brown Ankle High Leather Boots, Men Brogue Lace Up Chukka Boots

Men's Handmade Brown Ankle High Leather Boots, Men Brogue Lace Up Chukka Boots

$169.99$85.00

STEVE MADDEN Mens GNOMIE Chukka Boots 9 Brown Lace Up Leather NWOB

STEVE MADDEN Mens GNOMIE Chukka Boots 9 Brown Lace Up Leather NWOB

$54.00$27.00

Original Penguin Mens Size 8 Chukka Leather Boots Black

Original Penguin Mens Size 8 Chukka Leather Boots Black

$55.00$27.50

Brand New Pair Of George Brown Foster Lace-Up Chukka Boots TMORO Size 8

Brand New Pair Of George Brown Foster Lace-Up Chukka Boots TMORO Size 8

$35.00$17.50

Tommy Bahama Men's Brown Tan Leather Edisto Lace up Chukka Boots Size 13 M

Tommy Bahama Men's Brown Tan Leather Edisto Lace up Chukka Boots Size 13 M

$35.00$17.50

Born Shoes Men's 13 Nash Brown Suede Leather Chukka Lace Up Boots

Born Shoes Men's 13 Nash Brown Suede Leather Chukka Lace Up Boots

$29.99$14.99

Dexter Comfort Men's Sonoron Brown Chukka Boots Shoes Medium Width

Dexter Comfort Men's Sonoron Brown Chukka Boots Shoes Medium Width

$44.99$22.50

Clarks Wallabee FTRE 67237 Mens White Blue Green Chukka Boots Size US 8.5 FL1934

Clarks Wallabee FTRE 67237 Mens White Blue Green Chukka Boots Size US 8.5 FL1934

$74.95$37.48

DONALD PILNER Timm2 Mens 9.5 M Brown chukka boots Perforated Made In Brazil

DONALD PILNER Timm2 Mens 9.5 M Brown chukka boots Perforated Made In Brazil

$30.36$15.18

CLARKS COLLECTION Mens Black Bushacre 3 Toe Block Heel Leather Chukka Boots 7 M

CLARKS COLLECTION Mens Black Bushacre 3 Toe Block Heel Leather Chukka Boots 7 M

$31.95$15.97

Varese Gobi II Chukka Boots Mens Size 13 Ankle Brown Lace Up Model 350119

Varese Gobi II Chukka Boots Mens Size 13 Ankle Brown Lace Up Model 350119

$24.88$12.44

J. Shoes Monarch Brown Leather Lace-Up Plain Toe Shoes Chukka Boots Men Sz 11.5

J. Shoes Monarch Brown Leather Lace-Up Plain Toe Shoes Chukka Boots Men Sz 11.5

$34.77$17.39

Crevo Chestnut Mens Leather Chukka Boots

Crevo Chestnut Mens Leather Chukka Boots

$49.00$24.50

Bloomingdale's Black Chukka Boots Mens Size US 7.5

Bloomingdale's Black Chukka Boots Mens Size US 7.5

$51.97$25.98

New Sandro Moscoloni Terry Chukka men's Boots

New Sandro Moscoloni Terry Chukka men's Boots

$69.00$34.50

ARTEFACT CLOTHING MENS CASUAL SUEDE BOOTS PREOWNED SZ 11 BROWN

ARTEFACT CLOTHING MENS CASUAL SUEDE BOOTS PREOWNED SZ 11 BROWN

$30.00$15.00

Steve Madden P-Bowery Men's Chukka Boots, Black, Size 10

Steve Madden P-Bowery Men's Chukka Boots, Black, Size 10

$38.00$19.00

Merona Chukka Brown Man Made Leather Target Boot Size 7

Merona Chukka Brown Man Made Leather Target Boot Size 7

$19.90$9.95

Goodfellow & Co Men's Gibson Hybrid Chukka Brown Laced Ankle Bootie Sz 12 NEW

Goodfellow & Co Men's Gibson Hybrid Chukka Brown Laced Ankle Bootie Sz 12 NEW

$49.95$24.98

STRELLSON S171567 Black Suede Boots Mens Size 42 *

STRELLSON S171567 Black Suede Boots Mens Size 42 *

$24.50$12.25

Clark’s Leather Bushcare 2 chukka boots mens size 8

Clark’s Leather Bushcare 2 chukka boots mens size 8

$20.00$10.00

BUSSOLA Mauleon Ebony Brown Suede Lace Up Chukka Ankle Boot Men’s Size 42 US 9

BUSSOLA Mauleon Ebony Brown Suede Lace Up Chukka Ankle Boot Men’s Size 42 US 9

$50.00$25.00

Steve Madden Chukka boot, Cognac color, size US 10

Steve Madden Chukka boot, Cognac color, size US 10

$40.00$20.00

Nisolo Men’s Chavito Chukka Boots Brown Size 11.5 Lace Up

Nisolo Men’s Chavito Chukka Boots Brown Size 11.5 Lace Up

$54.97$27.48

Clarks Size 12 Black Leather Chukka Boots Kyros Limit Lace Up O

Clarks Size 12 Black Leather Chukka Boots Kyros Limit Lace Up O

$45.00$22.50

Hari Mari CanyonTrek II Chukka Boot 9 Brown Leather

Hari Mari CanyonTrek II Chukka Boot 9 Brown Leather

$40.00$20.00

Men's Luxury Handcrafted Chukka Boot - Pure Crocodile Pattern Leather Dress Wear

Men's Luxury Handcrafted Chukka Boot - Pure Crocodile Pattern Leather Dress Wear

$199.99$100.00

Men's Chukka Ankle Boots Casual Business Work Shoes for Men

Men's Chukka Ankle Boots Casual Business Work Shoes for Men

$68.50$34.25

NEW ETNIES CALIFAS ANKLE BOOTS MENS 8 CALIFAS PLUS X MIGHTY HEALTHY BOOTS CHUKKA

NEW ETNIES CALIFAS ANKLE BOOTS MENS 8 CALIFAS PLUS X MIGHTY HEALTHY BOOTS CHUKKA

$45.08$22.54

Territory Axel Mens Sz 9.5 Mens Ankle Boots Chestnut Leather Desert Chukka Boot

Territory Axel Mens Sz 9.5 Mens Ankle Boots Chestnut Leather Desert Chukka Boot

$35.00$17.50

Timberland Men Casual lace up Chukka Boots Black two tone Leather suede 10.5

Timberland Men Casual lace up Chukka Boots Black two tone Leather suede 10.5

$49.99$25.00

Clarks Mens Chukka Boot Tan Leather Lace Up Desert Boots Size 12 M

Clarks Mens Chukka Boot Tan Leather Lace Up Desert Boots Size 12 M

$59.95$29.98

Propét Mens Findley Suede Chukka Boot Tan Size 8.5 W Orthotic Diabetic Friendly

Propét Mens Findley Suede Chukka Boot Tan Size 8.5 W Orthotic Diabetic Friendly

$95.00$47.50

5912360 MSBT50 SAUNDERS MEN'S SHOES 10.5 M BROWN LEATHER BOOTS JOHNSTON & MURPHY

5912360 MSBT50 SAUNDERS MEN'S SHOES 10.5 M BROWN LEATHER BOOTS JOHNSTON & MURPHY

$79.95$39.98

Hawke & Co Leather Sand w/Blue Interior Mojave Ankle Boots Suede Lace Up M S12 M

Hawke & Co Leather Sand w/Blue Interior Mojave Ankle Boots Suede Lace Up M S12 M

$39.00$19.50

NEW SZ 12 Xray Men's Dover Boot BROWN

NEW SZ 12 Xray Men's Dover Boot BROWN

$49.50$24.75

Carrucci Black Leather Plain Toe Chukka Boot (11)

Carrucci Black Leather Plain Toe Chukka Boot (11)

$169.95$84.97

Men's Chukka Ankle Boots Casual Business Work Shoes for Men

Men's Chukka Ankle Boots Casual Business Work Shoes for Men

$81.00$40.50

H&M Black Suede Chukka Boots Size 11.5M Made in Portugal u-14G

H&M Black Suede Chukka Boots Size 11.5M Made in Portugal u-14G

$50.00$25.00

Fluchos Ankle Chukka Boots Men Sz 8 EU 41 Brown Distressed Leather Hipster Spain

Fluchos Ankle Chukka Boots Men Sz 8 EU 41 Brown Distressed Leather Hipster Spain

$39.00$19.50

Cole Haan Connery Chukka Boots Men's 8.5 NEW IN BOX

Cole Haan Connery Chukka Boots Men's 8.5 NEW IN BOX

$129.99$65.00

STACY ADAMS Mens Brown Octavius Toe Block Heel Leather Chukka Boots 8 M

STACY ADAMS Mens Brown Octavius Toe Block Heel Leather Chukka Boots 8 M

$48.99$24.50

Clarks Mens Remsen HI Leather Ankle Chukka Boots Shoes 26110709 Size 8 M

Clarks Mens Remsen HI Leather Ankle Chukka Boots Shoes 26110709 Size 8 M

$69.95$34.98

G H Bass & Co Mens Size 12 M Brown Ankle Tie Chukka Boots

G H Bass & Co Mens Size 12 M Brown Ankle Tie Chukka Boots

$39.99$20.00

FRED PERRY - Suede EATHER Mens 10.5 Chukka Ankle Boots

FRED PERRY - Suede EATHER Mens 10.5 Chukka Ankle Boots

$84.11$42.05

Johnston & Murphy Brown Leather Ankle Boots Men's 13M #25-6516

Johnston & Murphy Brown Leather Ankle Boots Men's 13M #25-6516

$39.95$19.98

Cole Haan Graydon Chukka Boots Casual Dress Men's Black 8

Cole Haan Graydon Chukka Boots Casual Dress Men's Black 8

$69.99$34.99

Church's Men's Jockey Brown Suede Ankle Lace-Up Boots Size UK 60 US 7 Unisex

Church's Men's Jockey Brown Suede Ankle Lace-Up Boots Size UK 60 US 7 Unisex

$250.00$125.00

Stacy Adams Ozzie Wingtip Ankle Boots Brown Leather 8.5 Chukka Side Zip Lace

Stacy Adams Ozzie Wingtip Ankle Boots Brown Leather 8.5 Chukka Side Zip Lace

$49.94$24.97

SONOMA CHUKKA BOOTS BAYPORT SZ 7

SONOMA CHUKKA BOOTS BAYPORT SZ 7

$25.00$12.50

NWOT Men's G.H.Bass Co. Brown Leather Chukka Ankle Boots Sz13 EU 48 713224-BRTN

NWOT Men's G.H.Bass Co. Brown Leather Chukka Ankle Boots Sz13 EU 48 713224-BRTN

$42.00$21.00

STEVE MADDEN Men's HARKEN Chukka Boot Desert Style Cognac Leather, 9.5 M US

STEVE MADDEN Men's HARKEN Chukka Boot Desert Style Cognac Leather, 9.5 M US

$34.95$17.48

JackThreads Men's Brown Suede Leather Low Top Chukka Boots size 9

JackThreads Men's Brown Suede Leather Low Top Chukka Boots size 9

$38.99$19.50

Kenneth Cole New York Black Suede Chukka Boots Size 11.5 u-14E

Kenneth Cole New York Black Suede Chukka Boots Size 11.5 u-14E

$40.00$20.00

Steve Madden 'Durban' Navy Blue Chukka Suede Leather Boots - Men's 9 M outdoor

Steve Madden 'Durban' Navy Blue Chukka Suede Leather Boots - Men's 9 M outdoor

$21.61$10.80

Red Wing Heritage 3137 Chukka Boots Mens 8 D Copper Rough Tough Leather USA New

Red Wing Heritage 3137 Chukka Boots Mens 8 D Copper Rough Tough Leather USA New

$245.00$122.50

Timberland Chukka Boots Excellent Brown 11.5 Leather Sensorflex Sole

Timberland Chukka Boots Excellent Brown 11.5 Leather Sensorflex Sole

$75.00$37.50

AMAPO Mens Casual Lightweight Chukka Boots Comfortable Black EU 42/US Size 9

AMAPO Mens Casual Lightweight Chukka Boots Comfortable Black EU 42/US Size 9

$24.99$12.49

Stacy Adams 11M Chukka Boots Mens Shoes Beige Suede Lace Up Ankle Desert

Stacy Adams 11M Chukka Boots Mens Shoes Beige Suede Lace Up Ankle Desert

$27.92$13.96

I.N.C Men Darius Patch Black Chukkas Boot’s

I.N.C Men Darius Patch Black Chukkas Boot’s

$54.00$27.00

Clarks sz 9 Bushacre Chukka boot boots gray leather lace up scuffed toes

Clarks sz 9 Bushacre Chukka boot boots gray leather lace up scuffed toes

$32.24$16.12

Executive Imperials Mens Dark Brown Leather Chukka Ankle Boots Lace Up 9B

Executive Imperials Mens Dark Brown Leather Chukka Ankle Boots Lace Up 9B

$29.99$14.99

STACY ADAMS Mens Brown Kyron Round Toe Block Heel Leather Chukka Boots 12 M

STACY ADAMS Mens Brown Kyron Round Toe Block Heel Leather Chukka Boots 12 M

$42.95$21.48

TOMMY BAHAMA CHUCCA BOOTS

TOMMY BAHAMA CHUCCA BOOTS

$21.00$10.50

BEN SHERMAN Brent Leather Plain Toe Chukka Boot Tan Men Lace Up Size 12 EUC

BEN SHERMAN Brent Leather Plain Toe Chukka Boot Tan Men Lace Up Size 12 EUC

$35.00$17.50

NEW $195 Hudson London Matteo Calf in Black Men's size 7 PWW

NEW $195 Hudson London Matteo Calf in Black Men's size 7 PWW

$99.00$49.50

VINCE CAMUTO Mens Black Comfort Soleh Round Toe Lace-Up Leather Chukka Boots

VINCE CAMUTO Mens Black Comfort Soleh Round Toe Lace-Up Leather Chukka Boots

$49.95$24.98

Salvatore Ferragamo Men's Studio Black Leather Chukka Boots- Size 7.5 D

Salvatore Ferragamo Men's Studio Black Leather Chukka Boots- Size 7.5 D

$100.00$50.00

Steve Madden Men’s 8 Saxxen Camel Sued Chukka Boot Leather

Steve Madden Men’s 8 Saxxen Camel Sued Chukka Boot Leather

$28.00$14.00

Rocawear Men’s Brown Chukka Boots Lace Up Size 10.5 Model R-7004

Rocawear Men’s Brown Chukka Boots Lace Up Size 10.5 Model R-7004

$24.22$12.11

Levi's Schuhe Canyon Lake Mid Lace Chukka Boot Brown Size 10

Levi's Schuhe Canyon Lake Mid Lace Chukka Boot Brown Size 10

$28.99$14.49

IZOD Men’s Chukka Boots sz 13 Pull On Smooth NEW

IZOD Men’s Chukka Boots sz 13 Pull On Smooth NEW

$39.96$19.98

Timberland 6 Inch Field Boots Medium Brown Nubuck Wheat TB 0A18BF 715

Timberland 6 Inch Field Boots Medium Brown Nubuck Wheat TB 0A18BF 715

$142.40$71.20

Painter Boots Sz 44 M Gray Round Toe Chukka Leather Men

Painter Boots Sz 44 M Gray Round Toe Chukka Leather Men

$24.00$12.00

Thorocraft Braxton Chukka Boots Black Leather And Wool Size 44(11)

Thorocraft Braxton Chukka Boots Black Leather And Wool Size 44(11)

$25.60$12.80

NWT BLONDO KEITH MEN'S BLACK SUEDE CHUKKA BOOTS 13 M

NWT BLONDO KEITH MEN'S BLACK SUEDE CHUKKA BOOTS 13 M

$69.00$34.50

204561 MSBT50 RALEIGH MEN'S SHOES 9 M BLACK LEATHER BOOTS JOHNSTON & MURPHY

204561 MSBT50 RALEIGH MEN'S SHOES 9 M BLACK LEATHER BOOTS JOHNSTON & MURPHY

$79.95$39.98

Testosterone C U Later Chukka Boots Ankle Boot Brown Leather Size 46 US 13

Testosterone C U Later Chukka Boots Ankle Boot Brown Leather Size 46 US 13

$29.99$14.99

5940825 MSBT50 MEN'S SHOES 10 M BLACK BOOTS J. MURPHY BY JOHNSTON & MURPHY

5940825 MSBT50 MEN'S SHOES 10 M BLACK BOOTS J. MURPHY BY JOHNSTON & MURPHY

$79.95$39.98

Manfield Ankle Boots Mens EU 43 Brown Leather Lace Up Zip Chukka

Manfield Ankle Boots Mens EU 43 Brown Leather Lace Up Zip Chukka

$47.20$23.60

Ugg Cali Chukka Boots Brown

Ugg Cali Chukka Boots Brown

$130.00$65.00

Designer Brand Mens Brown Round Toe Block Heel Lace-Up Leather Chukka Boots 7.5

Designer Brand Mens Brown Round Toe Block Heel Lace-Up Leather Chukka Boots 7.5

$52.57$26.29

WEATHERPROOF VINTAGE Mens Black Comfort Round Toe Lace-Up Chukka Boots 13 M

WEATHERPROOF VINTAGE Mens Black Comfort Round Toe Lace-Up Chukka Boots 13 M

$34.98$17.49

STACY ADAMS Mens Brown Kyron Round Toe Block Heel Leather Chukka Boots 12 M

STACY ADAMS Mens Brown Kyron Round Toe Block Heel Leather Chukka Boots 12 M

$42.95$21.48

BEN SHERMAN MEN'S GREEN LEATHER CHUKKA LACE-UP BOOTS SIZE 12

BEN SHERMAN MEN'S GREEN LEATHER CHUKKA LACE-UP BOOTS SIZE 12

$44.99$22.50

LM Brown Lether Chukka Boots Made in Italy Men Size 8

LM Brown Lether Chukka Boots Made in Italy Men Size 8

$45.00$22.50

Clark's Gerrard (72183) Ankle Brown Leather Boot Shoes Men's 13 M

Clark's Gerrard (72183) Ankle Brown Leather Boot Shoes Men's 13 M

$24.71$12.36

Clarks Canal Boots Mens sz. 8 Brown Leather

Clarks Canal Boots Mens sz. 8 Brown Leather

$25.00$12.50

Clarks Chukka Boots Mens 8.5 Bushacre Brown Leather 2 Eye Lace Up Boots

Clarks Chukka Boots Mens 8.5 Bushacre Brown Leather 2 Eye Lace Up Boots

$49.00$24.50

Swims lined Country Boots, chukka Brown, Mens 11.5 M

Swims lined Country Boots, chukka Brown, Mens 11.5 M

$50.93$25.46

Cole Haan Mens Lace Up Ankle Boots Chukka size 13 C24533

Cole Haan Mens Lace Up Ankle Boots Chukka size 13 C24533

$95.00$47.50

Arizona Men's Driftwood Chukka Boots Flat Heel Cognac Size 13

Arizona Men's Driftwood Chukka Boots Flat Heel Cognac Size 13

$24.99$12.49

VINCE CAMUTO Mens Brown Comfort Soleh Round Toe Leather Chukka Boots 10.5 M

VINCE CAMUTO Mens Brown Comfort Soleh Round Toe Leather Chukka Boots 10.5 M

$62.96$31.48

Lotus Wheeler Men's Chukka Black Leather Boots Size Uk 12 USA 13, NEW

Lotus Wheeler Men's Chukka Black Leather Boots Size Uk 12 USA 13, NEW

$36.96$18.48

Michael Shannon Mens Radcliffe Taupe Suede Lace Up Ankle Boots Size 12

Michael Shannon Mens Radcliffe Taupe Suede Lace Up Ankle Boots Size 12

$37.77$18.89

STACY ADAMS Mens Brown Kyron Round Toe Block Heel Leather Chukka Boots 11.5 M

STACY ADAMS Mens Brown Kyron Round Toe Block Heel Leather Chukka Boots 11.5 M

$29.96$14.98

Ben Sherman Mens Stateside Chukka Boot Brown Size 12 M

Ben Sherman Mens Stateside Chukka Boot Brown Size 12 M

$34.99$17.50

NEW JOHNNIE-O $198 MEN'S MALIBU CHUKKA ANKLE BOOTS IN TAUPE SZ 9

NEW JOHNNIE-O $198 MEN'S MALIBU CHUKKA ANKLE BOOTS IN TAUPE SZ 9

$64.99$32.49