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Johnnie-O Mens Chill Chukka 2.0 Brown Ankle Boots Size 12 (7747221)

Johnnie-O Mens Chill Chukka 2.0 Brown Ankle Boots Size 12 (7747221)

$66.99$33.49

The Men's Store at Bloomingdale's Leather Chukka Boots- Brown, US 8

The Men's Store at Bloomingdale's Leather Chukka Boots- Brown, US 8

$55.00$27.50

NEW JOHNNIE-O $198 MEN'S MALIBU CHUKKA ANKLE BOOTS IN TAUPE SZ 8

NEW JOHNNIE-O $198 MEN'S MALIBU CHUKKA ANKLE BOOTS IN TAUPE SZ 8

$64.99$32.49

Mens Real Cow Leather Chic Motorcycle Boots Shoes Biker Work Chukka Lace up New

Mens Real Cow Leather Chic Motorcycle Boots Shoes Biker Work Chukka Lace up New

$123.11$61.55

Steve Madden Shoes Mens 8 Chukka Boots Classic Leather Harsen Casual Comfort Mid

Steve Madden Shoes Mens 8 Chukka Boots Classic Leather Harsen Casual Comfort Mid

$59.97$29.98

Mens Sonoma Bayport Mahogany Chukka Boots Size 8 Medium

Mens Sonoma Bayport Mahogany Chukka Boots Size 8 Medium

$26.95$13.47

Clark's Chukka Boots Men's Size 14 Brown Leather Gray Laces

Clark's Chukka Boots Men's Size 14 Brown Leather Gray Laces

$26.22$13.11

red tape chukka boots mens 10 blue yarrow

red tape chukka boots mens 10 blue yarrow

$20.00$10.00

CLARKS COLLECTION Mens Brown Round Toe Lace-Up Leather Chukka Boots 7 M

CLARKS COLLECTION Mens Brown Round Toe Lace-Up Leather Chukka Boots 7 M

$35.97$17.98

IZOD Memory Foam Andrew Brown Oxford Chukka Boot Men's 10.5 Lace Up Fall Season

IZOD Memory Foam Andrew Brown Oxford Chukka Boot Men's 10.5 Lace Up Fall Season

$16.99$8.49

johnnie-O Mens The Chill Chelsea Brown Ankle Boots Size 11.5 (7672510)

johnnie-O Mens The Chill Chelsea Brown Ankle Boots Size 11.5 (7672510)

$66.99$33.49

Vince Men's Wayde Suede Chukka Boot Coastal Navy Blue Size US 9.5 $295🛒

Vince Men's Wayde Suede Chukka Boot Coastal Navy Blue Size US 9.5 $295🛒

$100.00$50.00

COLE HAAN LUNAR GRAND CHUKKA Comfort Suede Laced Up Ankle Boots Sz 11

COLE HAAN LUNAR GRAND CHUKKA Comfort Suede Laced Up Ankle Boots Sz 11

$89.95$44.98

Pikolinos Mens Santiago M7B-8012C1 Chukka Boots, Olmo/Garnet, 41 EU/7.5-8 US

Pikolinos Mens Santiago M7B-8012C1 Chukka Boots, Olmo/Garnet, 41 EU/7.5-8 US

$79.99$39.99

Italy Style Mens Retro Desert Ankle Boots Chukka Casual Lace Up Suede Boots

Italy Style Mens Retro Desert Ankle Boots Chukka Casual Lace Up Suede Boots

$151.49$75.75

johnnie-O Mens Chill Chukka 2.0 Brown Ankle Boots Size 9.5 (7672260)

johnnie-O Mens Chill Chukka 2.0 Brown Ankle Boots Size 9.5 (7672260)

$66.99$33.49

Size 10 Men's Timberland Euro Hiker Mid Waterproof Boots TB-0A64RD-033 Grey

Size 10 Men's Timberland Euro Hiker Mid Waterproof Boots TB-0A64RD-033 Grey

$96.55$48.27

Steve Madden Brown Chukka P-Iconik Boots size 7 Pre Owned

Steve Madden Brown Chukka P-Iconik Boots size 7 Pre Owned

$36.45$18.23

Rhino 62M28 6 inch Moc Toe Leather Work Boot - Brown

Rhino 62M28 6 inch Moc Toe Leather Work Boot - Brown

$54.95$27.48

XRAY Chukka Men's Size 7.5 Brown Avery Ankle Boot Lace-Up

XRAY Chukka Men's Size 7.5 Brown Avery Ankle Boot Lace-Up

$19.28$9.64

Stacy Adams Mens Ankle Boots 8M Chukka Boots Brown Leather 24690-245

Stacy Adams Mens Ankle Boots 8M Chukka Boots Brown Leather 24690-245

$44.98$22.49

Duck Head Mens Size 7.5M Brown Leather Chukka Boot Shoelace Up

Duck Head Mens Size 7.5M Brown Leather Chukka Boot Shoelace Up

$40.00$20.00

Mecca since Day One navy blue chukka boot size 10

Mecca since Day One navy blue chukka boot size 10

$39.99$20.00

J Artola Brown Leather & Canvas Lace Up Chukka Boots Mens 9 (f6a)

J Artola Brown Leather & Canvas Lace Up Chukka Boots Mens 9 (f6a)

$31.99$15.99

Dr. Martens Rakim Utility Chukka Combat Boots Women's Size 6

Dr. Martens Rakim Utility Chukka Combat Boots Women's Size 6

$45.00$22.50

Stacy Adams Men's Delaney Brown Leather/Suede Chukka Boots 25053-200

Stacy Adams Men's Delaney Brown Leather/Suede Chukka Boots 25053-200

$69.99$34.99

Merrell World Excursion Chukka Boots Men’s Sz 13 Brown Leather Lace Up Outdoor

Merrell World Excursion Chukka Boots Men’s Sz 13 Brown Leather Lace Up Outdoor

$42.00$21.00

johnnie-O Mens Chill Chukka 2.0 Brown Ankle Boots Size 10 (7672373)

johnnie-O Mens Chill Chukka 2.0 Brown Ankle Boots Size 10 (7672373)

$66.99$33.49

Men's Brogue Work Ankle Boots Shoes Wing Tip Carved Chukka Round Toe Walking L

Men's Brogue Work Ankle Boots Shoes Wing Tip Carved Chukka Round Toe Walking L

$50.84$25.42

Bedstu Mens Rayburn Chukka Boot Cognac Size 11.5 M

Bedstu Mens Rayburn Chukka Boot Cognac Size 11.5 M

$160.10$80.05

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

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

$85.00$42.50

Vtg Js Monarch Suede Chukka Boot Lace Up WhimsiGoth Grunge Academia Gorpcore

Vtg Js Monarch Suede Chukka Boot Lace Up WhimsiGoth Grunge Academia Gorpcore

$39.88$19.94

Cole Haan Air Jameson Chukka

Cole Haan Air Jameson Chukka

$65.00$32.50

H By Hudson London Men's Gray Suede Chukka Boots - Size 11 EU 44. VGUC. D5

H By Hudson London Men's Gray Suede Chukka Boots - Size 11 EU 44. VGUC. D5

$39.00$19.50

New Steve Madden Mens Chukka Boots P-Bleekr Black Sz. 13 Lace Up Ortholite

New Steve Madden Mens Chukka Boots P-Bleekr Black Sz. 13 Lace Up Ortholite

$35.00$17.50

Chippewa Milford Men's Suede Chukka Boots Blue, Made In USA, Size 9 E

Chippewa Milford Men's Suede Chukka Boots Blue, Made In USA, Size 9 E

$52.00$26.00

RED WING FOREMAN MEN SZ 42 / US 9 D BROWN LEATHER CHUKKA WORK ANKLE BOOTS #9219

RED WING FOREMAN MEN SZ 42 / US 9 D BROWN LEATHER CHUKKA WORK ANKLE BOOTS #9219

$99.99$49.99

CALVIN KLEIN Mens Black Cushioned Alory Round Toe Lace-Up Chukka Boots 11.5 M

CALVIN KLEIN Mens Black Cushioned Alory Round Toe Lace-Up Chukka Boots 11.5 M

$61.83$30.91

UGG Neumel Men's Chukka Boots Chestnut Size 6 New

UGG Neumel Men's Chukka Boots Chestnut Size 6 New

$129.99$65.00

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

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

$85.00$42.50

NWOB Cole Haan C35598 Water Resistant Zerogrand Black Boots

NWOB Cole Haan C35598 Water Resistant Zerogrand Black Boots

$59.95$29.98

Tommy Hilfiger Mens Chukka Brown Fashion Hyder Industrial Lace-Up Boots Sz 12

Tommy Hilfiger Mens Chukka Brown Fashion Hyder Industrial Lace-Up Boots Sz 12

$74.99$37.49

Nordstrom Men's Shop Hudson Brown Leather Lace Up Rugged Sole Chukka Boot SZ 8

Nordstrom Men's Shop Hudson Brown Leather Lace Up Rugged Sole Chukka Boot SZ 8

$52.00$26.00

TOMS Men's Classic Chukka Water Resistant Boot Leather Black

TOMS Men's Classic Chukka Water Resistant Boot Leather Black

$69.99$34.99

Georgia Boot Men's Wedge Chukka Work Boot GB1222

Georgia Boot Men's Wedge Chukka Work Boot GB1222

$140.00$70.00

johnnie-O Mens Chill Chukka 2.0 Gray Ankle Boots Size 13 (7672124)

johnnie-O Mens Chill Chukka 2.0 Gray Ankle Boots Size 13 (7672124)

$66.99$33.49

johnnie-O Mens Chill Chukka 2.0 Brown Ankle Boots Size 9.5 (7672576)

johnnie-O Mens Chill Chukka 2.0 Brown Ankle Boots Size 9.5 (7672576)

$66.99$33.49

Stacy Adams Men's 7.5 M Dabney Suede Lace Up Chukka Ankle Boots Brown

Stacy Adams Men's 7.5 M Dabney Suede Lace Up Chukka Ankle Boots Brown

$38.00$19.00

ECCO S Lite Hybrid GORE-TEX® Waterproof CHUKKA Boots 47 / 13 - 13.5

ECCO S Lite Hybrid GORE-TEX® Waterproof CHUKKA Boots 47 / 13 - 13.5

$65.00$32.50

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

Calfskin Lace-Up Chukka Boot Cognac 7.5 US Men’s

Calfskin Lace-Up Chukka Boot Cognac 7.5 US Men’s

$79.99$39.99

Trask Boots Mens Two Eye Chukka Boot 30-0892 Brown Leather Lace Up Size 11.5M

Trask Boots Mens Two Eye Chukka Boot 30-0892 Brown Leather Lace Up Size 11.5M

$37.99$19.00

NEW Wally Walker Chukka Canvas Boots Men's Shous Made in Italy Size 42

NEW Wally Walker Chukka Canvas Boots Men's Shous Made in Italy Size 42

$60.00$30.00

Cole Haan Midland Lug Sole Chukka Boot Men's 11

Cole Haan Midland Lug Sole Chukka Boot Men's 11

$109.99$54.99

johnnie-O Mens Chill Chukka 2.0 Gray Ankle Boots Size 10 (7672364)

johnnie-O Mens Chill Chukka 2.0 Gray Ankle Boots Size 10 (7672364)

$66.99$33.49

johnnie-O Mens Chill Chukka 2.0 Gray Ankle Boots Size 12 (7672217)

johnnie-O Mens Chill Chukka 2.0 Gray Ankle Boots Size 12 (7672217)

$66.99$33.49

johnnie-O Mens Chill Chukka 2.0 Brown Ankle Boots Size 10 (7672462)

johnnie-O Mens Chill Chukka 2.0 Brown Ankle Boots Size 10 (7672462)

$66.99$33.49

Carven Men's Fringe Chukka Sneakers Cognac EUR 42 US 9

Carven Men's Fringe Chukka Sneakers Cognac EUR 42 US 9

$148.50$74.25

Florsheim Limited Men's Brown Leather Wingtip Lace Up Chukka Ankle Boots Sz 11 D

Florsheim Limited Men's Brown Leather Wingtip Lace Up Chukka Ankle Boots Sz 11 D

$79.99$39.99

Work America Chukka Boots Brown Size 7E 557-8 Men's Leather

Work America Chukka Boots Brown Size 7E 557-8 Men's Leather

$37.00$18.50

IZOD Inwood Men's Chukka Boot Size 10.5M Beige Memory Foam

IZOD Inwood Men's Chukka Boot Size 10.5M Beige Memory Foam

$22.50$11.25

LA Milano Black Leather Oxford Ankle Square Toe Chukka Boots Shoes size 12

LA Milano Black Leather Oxford Ankle Square Toe Chukka Boots Shoes size 12

$29.99$14.99

Clarks Desert Boot 2 Beeswax Leather US Men's 10.5W

Clarks Desert Boot 2 Beeswax Leather US Men's 10.5W

$64.99$32.49

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

Sonoma Goods For Life® Freer Mid Men's Chukka Boots size 7

Sonoma Goods For Life® Freer Mid Men's Chukka Boots size 7

$31.49$15.74

Dapper shoes Men's Boot Grain Mid Brown US 10 -Nos

Dapper shoes Men's Boot Grain Mid Brown US 10 -Nos

$69.99$34.99

Goodbye Folk Men’s 40 Black Leather Lace Up Boots

Goodbye Folk Men’s 40 Black Leather Lace Up Boots

$59.00$29.50

Men's NEXT Leather Chukka Boots Brown US 10 EU 44 Red Trim Sole

Men's NEXT Leather Chukka Boots Brown US 10 EU 44 Red Trim Sole

$31.99$15.99

SELECTED HOMME Leather Suede Ankle Chukka Boots Brown Sz 43

SELECTED HOMME Leather Suede Ankle Chukka Boots Brown Sz 43

$49.00$24.50

johnnie-O Mens The Chill Chukka Taupe Ankle Boots Size 10 (7672605)

johnnie-O Mens The Chill Chukka Taupe Ankle Boots Size 10 (7672605)

$66.99$33.49

Alegria leather boots size 42

Alegria leather boots size 42

$50.00$25.00

Clarks Originals Wallabee Boots Mens 9.5 US Extreme Comfort Brown Leather NO BOX

Clarks Originals Wallabee Boots Mens 9.5 US Extreme Comfort Brown Leather NO BOX

$20.00$10.00

STACY ADAMS Mens Brown Kyron Round Toe Block Heel Leather Chukka Boots 8.5 M

STACY ADAMS Mens Brown Kyron Round Toe Block Heel Leather Chukka Boots 8.5 M

$45.99$23.00

Zanzara Smith Nafpl 10 Leather Shoes Cognac Chukka Wingtip Ankle Boots Sz 13

Zanzara Smith Nafpl 10 Leather Shoes Cognac Chukka Wingtip Ankle Boots Sz 13

$142.95$71.47

UGG BLACK NEUMEL SNAPBACK SUEDE/ WOOL ANKLE BOOTS, MEN US 8/ EUR 41 ~NEW

UGG BLACK NEUMEL SNAPBACK SUEDE/ WOOL ANKLE BOOTS, MEN US 8/ EUR 41 ~NEW

$109.95$54.98

FLYLAND Men's Classical Vintage Genuine Leather Chukka Boots Casual Outdoor Shoe

FLYLAND Men's Classical Vintage Genuine Leather Chukka Boots Casual Outdoor Shoe

$49.99$25.00

EASY SPIRIT Mens Brown Bento Round Toe Lace-Up Leather Chukka Boots 9.5

EASY SPIRIT Mens Brown Bento Round Toe Lace-Up Leather Chukka Boots 9.5

$64.98$32.49

johnnie-O Mens Chill Chukka 2.0 Brown Ankle Boots Size 9.5 (7672460)

johnnie-O Mens Chill Chukka 2.0 Brown Ankle Boots Size 9.5 (7672460)

$66.99$33.49

Cl Factory Men's Suede Blue Chukka Boots Lace-up Size 45 (12US)

Cl Factory Men's Suede Blue Chukka Boots Lace-up Size 45 (12US)

$35.00$17.50

Mens Dark Brown Skechers Waterproof, Relaxed-Fit Memory Foam Boot Sz 9 NIB

Mens Dark Brown Skechers Waterproof, Relaxed-Fit Memory Foam Boot Sz 9 NIB

$70.00$35.00

Ben Sherman Kent Casual Chukka Boot Men's

Ben Sherman Kent Casual Chukka Boot Men's

$69.99$34.99

Nunn Bush Barklay Chukka Gray Leather Casual Boots Mens 10

Nunn Bush Barklay Chukka Gray Leather Casual Boots Mens 10

$22.88$11.44

Sonoma Mens Grizzley Brown Ankle Boots NWOB Size 10 Lace Up Round Toe Thick Heel

Sonoma Mens Grizzley Brown Ankle Boots NWOB Size 10 Lace Up Round Toe Thick Heel

$35.00$17.50

Mossy Oak Chukka Driving Boots Size 7 1/2 Medium Camo New with Tags MXC0008

Mossy Oak Chukka Driving Boots Size 7 1/2 Medium Camo New with Tags MXC0008

$30.00$15.00

Clarks Bushacre Beeswax Leather Brown Chukka Boots Men's Size 7.5M

Clarks Bushacre Beeswax Leather Brown Chukka Boots Men's Size 7.5M

$60.00$30.00

Freeman 1921 Brent Chukka Brown Mens Boots Size 10 M

Freeman 1921 Brent Chukka Brown Mens Boots Size 10 M

$34.99$17.50

Steve Madden Mens Harken 247 Brown Cognac Leather Chukka Ankle Boots Size 13

Steve Madden Mens Harken 247 Brown Cognac Leather Chukka Ankle Boots Size 13

$29.99$14.99

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

$34.97$17.48

Mix No 6 Mens Baiyard Chukka Boot Brown Size 10.5 M

Mix No 6 Mens Baiyard Chukka Boot Brown Size 10.5 M

$40.00$20.00

Jeep Shoes Brown Suede Chukka Boot Men's Lace up Size EU 43

Jeep Shoes Brown Suede Chukka Boot Men's Lace up Size EU 43

$61.75$30.88

CALVIN KLEIN Mens Black Cushioned Alory Round Toe Lace-Up Chukka Boots 11.5 M

CALVIN KLEIN Mens Black Cushioned Alory Round Toe Lace-Up Chukka Boots 11.5 M

$61.83$30.91

Madden Mens M-Hinton Leather Almond Toe Chukka Boots Size 9.5

Madden Mens M-Hinton Leather Almond Toe Chukka Boots Size 9.5

$49.99$25.00

Johnston & Murphy Men's Copeland BLACK LEATHER Chelsea Boots many Sizes 11

Johnston & Murphy Men's Copeland BLACK LEATHER Chelsea Boots many Sizes 11

$75.00$37.50

Ben Sherman Nu Casual Chukka Boots Size 11 Blue Mens

Ben Sherman Nu Casual Chukka Boots Size 11 Blue Mens

$25.00$12.50

UGG Neumel Red Boots

UGG Neumel Red Boots

$115.00$57.50

Clarks Bushacre 2 Brown Leather Chukka Lace Up Boots 15522 Men's 7 US 39.5 EU

Clarks Bushacre 2 Brown Leather Chukka Lace Up Boots 15522 Men's 7 US 39.5 EU

$29.99$14.99

Clarks Men’s Ankle Boots Size 7 M Leather Upper Brown Lace Up Shoes

Clarks Men’s Ankle Boots Size 7 M Leather Upper Brown Lace Up Shoes

$35.00$17.50

Blue Hill Trading Company Tan Leather Chukka Boots Thick Tread size 9

Blue Hill Trading Company Tan Leather Chukka Boots Thick Tread size 9

$25.00$12.50

Clarks Bushacre 3 Sand Waxy Suede Shoes Men Size 9.5 (h446)

Clarks Bushacre 3 Sand Waxy Suede Shoes Men Size 9.5 (h446)

$89.99$44.99

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