Chukka Boots & Desert Boots for Men

New Markdown

Johnston & Murphy

Boswell Chukka Boot (Men)

$67.47 – $89.97Current Price $67.47 to $89.97

(Up to 61% off select items)Up to 61% off select items.

$175.00Comparable value $175.00

(12)

New Markdown

Tommy Hilfiger

Harbin Chukka Boot (Men)

$38.98 – $59.97Current Price $38.98 to $59.97

(Up to 67% off select items)Up to 67% off select items.

$119.00Comparable value $119.00

(10)

Børn

Theo Chukka Boot (Men)

$55.96 – $59.96Current Price $55.96 to $59.96

(Up to 56% off)Up to 56% off.

$130.00Comparable value $130.00

(9)

NUNN BUSH

Otto Chukka Boot - Wide Width Available (Men)

$33.72 – $79.97Current Price $33.72 to $79.97

(Up to 64% off select items)Up to 64% off select items.

$95.00 – $110.00Comparable value $95.00 to $110.00

(14)

Hawker Rye

Garner Chukka Boot (Men)

$29.96Current Price $29.96

(66% off)66% off.

$89.00Comparable value $89.00

Deer Stags

Garfield Plain Toe Chukka Boot (Men)

$64.97Current Price $64.97

(35% off)35% off.

$100.00Comparable value $100.00

Florsheim

Azzano Plain Toe Chukka Boot (Men)

$82.47Current Price $82.47

(43% off)43% off.

$145.00Comparable value $145.00

Steve Madden

Hemet Chukka Boot (Men)

$49.99 – $56.22Current Price $49.99 to $56.22

(Up to 61% off)Up to 61% off.

$130.00Comparable value $130.00

(3)

New Markdown

Cole Haan

Morse GRANDFØAM Chukka Boot (Men)

$84.48 – $129.97Current Price $84.48 to $129.97

(Up to 61% off select items)Up to 61% off select items.

$220.00Comparable value $220.00

(1)

NUNN BUSH

Ozark II Chukka Boot (Men)

$89.97Current Price $89.97

(18% off)18% off.

$110.00Comparable value $110.00

(3)

ALDO

Jefry Chukka Boot (Men)

$49.99Current Price $49.99

(64% off)64% off.

$140.00Comparable value $140.00

Cole Haan

2.Zerogrand Chukka Boot (Men)

$74.96 – $99.97Current Price $74.96 to $99.97

(Up to 77% off select items)Up to 77% off select items.

$338.00Comparable value $338.00

(400)

Cole Haan

Grand Atlantic Chukka Boot - Wide Width Available (Men)

$74.96Current Price $74.96

(62% off)62% off.

$200.00Comparable value $200.00

(42)

New!

Johnston & Murphy

Upton Chukka (Men)

$129.97Current Price $129.97

(27% off)27% off.

$179.00Comparable value $179.00

NUNN BUSH

Chase Plain Toe Chukka Boot - Wide Width Available (Men)

$32.48 – $54.97Current Price $32.48 to $54.97

(Up to 65% off select items)Up to 65% off select items.

$95.00Comparable value $95.00

(13)

Børn

Thomson Chukka Boot (Men)

$62.96Current Price $62.96

(51% off)51% off.

$130.00Comparable value $130.00

(26)

Johnston & Murphy

Calder Chukka Boot (Men)

$59.96Current Price $59.96

(63% off)63% off.

$165.00Comparable value $165.00

(21)

NUNN BUSH

Denali Waterproof Plain Toe Boot - Wide Width Available

$99.97Current Price $99.97

(16% off)16% off.

$120.00Comparable value $120.00

(1)

Tommy Hilfiger

Blaze Lace Cap Toe Boot (Men)

$59.97Current Price $59.97

(49% off)49% off.

$119.00Comparable value $119.00

Johnston & Murphy

Upton Chukka Boot (Men)

$49.99Current Price $49.99

(70% off)70% off.

$169.00Comparable value $169.00

(19)

Dockers®

Esmond Chukka Boot (Men)

$59.97Current Price $59.97

(36% off)36% off.

$95.00Comparable value $95.00

(4)

Ben Sherman

Whitby Chukka Boot (Men)

$49.97Current Price $49.97

(Up to 47% off)Up to 47% off.

$75.00 – $95.00Comparable value $75.00 to $95.00

(4)

Allen Edmonds

Caden Lug Sole Chukka Boot (Men)

$199.97Current Price $199.97

(63% off)63% off.

$550.00Comparable value $550.00

NUNN BUSH

Delton Plain Toe Chukka Boot (Men)

$54.97Current Price $54.97

(42% off)42% off.

$95.00Comparable value $95.00

Allen Edmonds

Carson Hybrid Chukka Boot (Men)

$97.48 – $149.97Current Price $97.48 to $149.97

(Up to 71% off select items)Up to 71% off select items.

$345.00Comparable value $345.00

(30)

Clarks®

Shepton Chukka Boot (Men)

$56.22 – $74.97Current Price $56.22 to $74.97

(Up to 43% off select items)Up to 43% off select items.

$100.00 – $110.00Comparable value $100.00 to $110.00

(3)

Hawker Rye

Breck Chukka Boot (Men)

$24.99Current Price $24.99

(71% off)71% off.

$89.00Comparable value $89.00

(1)

Donald Pliner

Kingston Chukka Boot (Men)

$139.97Current Price $139.97

(56% off)56% off.

$325.00Comparable value $325.00

(2)

Tommy Hilfiger

Bage Chukka Boot (Men)

$59.97 – $64.97Current Price $59.97 to $64.97

(Up to 49% off)Up to 49% off.

$119.00Comparable value $119.00

(6)

La Milano

Across II Cap Toe Chukka Boot (Men)

$79.97Current Price $79.97

(20% off)20% off.

$99.99Comparable value $99.99

New Markdown

VINTAGE FOUNDRY

Treyton Chukka Boot (Men)

$59.98 – $64.98Current Price $59.98 to $64.98

(Up to 70% off)Up to 70% off.

$200.00Comparable value $200.00

(6)

VITTORIO RUSSO

Whitman Chukka Boot (Men)

$129.97Current Price $129.97

(42% off)42% off.

$225.00Comparable value $225.00

(1)

TO BOOT NEW YORK

Horace Chukka Boot (Men)

$199.97Current Price $199.97

(52% off)52% off.

$425.00Comparable value $425.00

VANCE CO

Austin Cap Toe Chukka Boot - Wide Width (Men)

$39.99Current Price $39.99

(55% off)55% off.

$89.99Comparable value $89.99

(3)

Magnanni

Eddison Chukka Boot (Men)

$187.47 – $249.97Current Price $187.47 to $249.97

(Up to 59% off select items)Up to 59% off select items.

$465.00Comparable value $465.00

(2)

New!

Thomas & Vine

Keegan Chukka Boot

$79.97Current Price $79.97

(23% off)23% off.

$104.97Comparable value $104.97

(2)

New!

Dune London

Claus Chukka Boot (Men)

$89.97Current Price $89.97

(52% off)52% off.

$190.00Comparable value $190.00

Børn

Seth Chukka Boot (Men)

$67.47Current Price $67.47

(51% off)51% off.

$140.00Comparable value $140.00

(7)

Cole Haan

Chamberlin Grand Chukka Boot (Men)

$97.47 – $129.97Current Price $97.47 to $129.97

(Up to 66% off select items)Up to 66% off select items.

$290.00Comparable value $290.00

(3)

TO BOOT NEW YORK

Rosemead Chukka Boot (Men)

$123.48 – $142.47Current Price $123.48 to $142.47

(Up to 69% off)Up to 69% off.

$399.00Comparable value $399.00

Dockers®

Esmond Plain Toe Chukka Boot (Men)

$59.97Current Price $59.97

(29% off)29% off.

$85.00Comparable value $85.00

(9)

VANCE CO

Stratton Chukka Boot (Men)

$74.97Current Price $74.97

(31% off)31% off.

$109.99Comparable value $109.99

Ben Sherman

Thames Chukka Boot (Men)

$59.97Current Price $59.97

(40% off)40% off.

$100.00Comparable value $100.00

New!

Ariat

Spitfire Leather Chukka Boot (Men)

$69.97Current Price $69.97

(50% off)50% off.

$139.95Comparable value $139.95

(43)

Børn

Lincoln Chukka (Men)

$67.47 – $89.97Current Price $67.47 to $89.97

(Up to 56% off select items)Up to 56% off select items.

$155.00Comparable value $155.00

(5)

NUNN BUSH

Circuit Plain Toe Chukka Boot - Wide Width Available (Men)

$41.22 – $54.97Current Price $41.22 to $54.97

(Up to 54% off select items)Up to 54% off select items.

$90.00Comparable value $90.00

(17)

Clarks®

Walpath Waterproof Chukka Boot (Men)

$99.97Current Price $99.97

(23% off)23% off.

$130.00Comparable value $130.00

(1)

Only a few left

New Markdown

Børn

Eli Suede Chukka Boot (Men)

$58.48 – $67.47Current Price $58.48 to $67.47

(Up to 55% off)Up to 55% off.

$130.00Comparable value $130.00

(3)

Allen Edmonds

Downing Chukka Boot (Men)

$169.97Current Price $169.97

(65% off)65% off.

$495.00Comparable value $495.00

(10)

Cole Haan

Grand Remix Chukka Boot (Men)

$99.97Current Price $99.97

(Up to 56% off)Up to 56% off.

$220.00 – $230.00Comparable value $220.00 to $230.00

(14)

Donald Pliner

Kingston Chukka Boot (Men)

$149.97Current Price $149.97

(53% off)53% off.

$325.00Comparable value $325.00

(2)

Barbour

Readhead Chukka Boot (Men)

$60.48 – $109.97Current Price $60.48 to $109.97

(Up to 72% off select items)Up to 72% off select items.

$220.00Comparable value $220.00

(2)

Vince

Dann Lugged Chukka Boot (Men)

$119.96 – $159.97Current Price $119.96 to $159.97

(Up to 68% off select items)Up to 68% off select items.

$375.00Comparable value $375.00

(4)

TO BOOT NEW YORK

Johnnie Chukka Boot (Men)

$199.97Current Price $199.97

(52% off)52% off.

$425.00Comparable value $425.00

Allen Edmonds

Donovan Chukka Boot (Men)

$129.98 – $199.97Current Price $129.98 to $199.97

(Up to 73% off select items)Up to 73% off select items.

$495.00Comparable value $495.00

(1)

VINTAGE FOUNDRY

Marlow Chukka Boot (Men)

$54.97Current Price $54.97

(70% off)70% off.

$185.00Comparable value $185.00

Eastland

Patterson Cap Toe Chukka Boot (Men)

$44.96Current Price $44.96

(50% off)50% off.

$90.00Comparable value $90.00

Eastland

Jack Chukka Boot (Men)

$58.48Current Price $58.48

(53% off)53% off.

$125.00Comparable value $125.00

(1)

Brooks Brothers

Claremont Chukka (Men)

$169.97Current Price $169.97

(62% off)62% off.

$449.00Comparable value $449.00

(1)

Mykos

Koen Chukka Boot (Men)

$49.99 – $74.97Current Price $49.99 to $74.97

(Up to 47% off select items)Up to 47% off select items.

$94.99Comparable value $94.99

New!

Ariat

Spitfire Leather Chukka Boot (Men)

$59.97Current Price $59.97

(53% off)53% off.

$129.95Comparable value $129.95

(314)

RESERVE FOOTWEAR

Baryon Leather Chukka Boot (Men)

$79.97Current Price $79.97

(32% off)32% off.

$119.00Comparable value $119.00

Only a few left

VANCE CO

Jimmy Plain Toe Vegan Leather Chukka Boot (Men)

$39.99Current Price $39.99

(63% off)63% off.

$109.99Comparable value $109.99

Only a few left

Allen Edmonds

Grady Chukka Boot (Men)

$189.97 – $249.97Current Price $189.97 to $249.97

(Up to 65% off)Up to 65% off.

$550.00Comparable value $550.00

New Markdown

Timberland

Newmarket Chukka Boot (Men)

$58.48Current Price $58.48

(61% off)61% off.

$150.00Comparable value $150.00

(6)

Barbour

Boulder Chukka Boot (Men)

$83.96Current Price $83.96

(63% off)63% off.

$230.00Comparable value $230.00

(1)

Frye

Bowery Chukka Boot (Men)

$123.50Current Price $123.50

(64% off)64% off.

$348.00Comparable value $348.00

(51)

New Markdown

Allen Edmonds

Chandler Lug Chukka Boot (Men)

$129.98 – $199.97Current Price $129.98 to $199.97

(Up to 73% off select items)Up to 73% off select items.

$495.00Comparable value $495.00

(35)

Dune London

Clydell Chukka Boot (Men)

$74.96Current Price $74.96

(61% off)61% off.

$195.00Comparable value $195.00

UGG®

Neumel Chukka Boot (Men)

$109.97Current Price $109.97

(26% off)26% off.

$150.00Comparable value $150.00

(461)

Only a few left

Bruno Magli

Mabelton Chukka Boot (Men)

$179.97Current Price $179.97

(57% off)57% off.

$425.00Comparable value $425.00

New Markdown

SPERRY TOP-SIDER®

Authentic Original Chukka Boot (Men)

$37.47Current Price $37.47

(71% off)71% off.

$130.00Comparable value $130.00

(5)