Comfort 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)

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)

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)

New!

Florsheim

Chalet Chelsea Boot (Men)

$99.97Current Price $99.97

(31% off)31% off.

$145.00Comparable value $145.00

(116)

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)

New Markdown

Cole Haan

Chamberlin Grand Water Resistant Chelsea Boot (Men)

$97.47Current Price $97.47

(62% off)62% off.

$260.00Comparable value $260.00

(10)

Johnston & Murphy

Borland Chelsea Boot (Men)

$55.96 – $79.97Current Price $55.96 to $79.97

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

$160.00Comparable value $160.00

(2)

New Markdown

Cole Haan

Grand Atlantic Chelsea Boot (Men)

$74.96Current Price $74.96

(62% off)62% off.

$200.00Comparable value $200.00

(3)

Johnston & Murphy

Calder Chukka Boot (Men)

$59.96Current Price $59.96

(63% off)63% off.

$165.00Comparable value $165.00

(21)

Clarks®

Shepton Easy Chelsea Boot (Men)

$94.97Current Price $94.97

(26% off)26% off.

$130.00Comparable value $130.00

Clarks®

Weltridge Side Zip Boot (Men)

$94.97Current Price $94.97

(26% off)26% off.

$130.00Comparable value $130.00

(2)

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)

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)

Børn

Thomson Chukka Boot (Men)

$62.96Current Price $62.96

(51% off)51% off.

$130.00Comparable value $130.00

(26)

Børn

Seth Chukka Boot (Men)

$67.47Current Price $67.47

(51% off)51% off.

$140.00Comparable value $140.00

(7)

Sperry

Clifton Waterproof Chelsea Duck Boot (Men)

$49.97Current Price $49.97

(54% off)54% off.

$110.00Comparable value $110.00

Eastland

Jack Chukka Boot (Men)

$58.48Current Price $58.48

(53% off)53% off.

$125.00Comparable value $125.00

(1)

New Markdown

Timberland

Attleboro Chelsea Boot (Men)

$49.99Current Price $49.99

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

$130.00 – $140.00Comparable value $130.00 to $140.00

(7)

Sperry

Avenue Duck Boot (Men)

$44.97Current Price $44.97

(62% off)62% off.

$120.00Comparable value $120.00

(16)

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)

Florsheim

Azzano Plain Toe Chukka Boot (Men)

$82.47Current Price $82.47

(43% off)43% off.

$145.00Comparable value $145.00

New!

Cole Haan

Grand Lug Boot (Men)

$89.97Current Price $89.97

(43% off)43% off.

$160.00Comparable value $160.00

Eastland

'Lumber Up' Moc Toe Boot (Men)

$59.96 – $99.97Current Price $59.96 to $99.97

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

$135.00 – $150.00Comparable value $135.00 to $150.00

(4)

New!

Ariat

Sport Stratten Leather Boot (Men)

$99.97Current Price $99.97

(47% off)47% off.

$189.95Comparable value $189.95

(64)

Dockers®

Esmond Chukka Boot (Men)

$59.97Current Price $59.97

(36% off)36% off.

$95.00Comparable value $95.00

(4)

Ariat

'Lookout' Moc Toe Boot (Men)

$79.97Current Price $79.97

(50% off)50% off.

$159.95Comparable value $159.95

(69)

Johnston & Murphy

Brody Chelsea Boot (Men)

$69.97Current Price $69.97

(57% off)57% off.

$165.00Comparable value $165.00

(19)

Florsheim

Ruvo Chelsea Boot (Men)

$82.47Current Price $82.47

(45% off)45% off.

$150.00Comparable value $150.00

(22)

Dockers®

Dustin Boot (Men)

$59.97Current Price $59.97

(36% off)36% off.

$95.00Comparable value $95.00

(2)

New Markdown

Timberland

Newmarket Chukka Boot (Men)

$58.48Current Price $58.48

(61% off)61% off.

$150.00Comparable value $150.00

(6)

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)

New!

Johnston & Murphy

Upton Chukka (Men)

$129.97Current Price $129.97

(27% off)27% off.

$179.00Comparable value $179.00

Clarks®

Maplewalk Rise Boot (Men)

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

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

$120.00Comparable value $120.00

NUNN BUSH

Ozark II Chukka Boot (Men)

$89.97Current Price $89.97

(18% off)18% off.

$110.00Comparable value $110.00

(3)

Dockers®

Esmond Plain Toe Chukka Boot (Men)

$59.97Current Price $59.97

(29% off)29% off.

$85.00Comparable value $85.00

(9)

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)

NUNN BUSH

Karnak Water Resistant Plain Toe Boot (Men)

$89.97Current Price $89.97

(18% off)18% off.

$110.00Comparable value $110.00

New Markdown

Clarks®

Wallaston Chukka Boot (Men)

$59.96 – $79.97Current Price $59.96 to $79.97

(Up to 50% off select items)Up to 50% off select items.

$120.00Comparable value $120.00

(2)

UGG®

Burleigh Chukka (Men)

$89.97Current Price $89.97

(43% off)43% off.

$160.00Comparable value $160.00

(19)

Only a few left

New!

Ariat

Spitfire Leather Chukka Boot (Men)

$69.97Current Price $69.97

(50% off)50% off.

$139.95Comparable value $139.95

(43)

Deer Stags

Garfield Plain Toe Chukka Boot (Men)

$64.97Current Price $64.97

(35% off)35% off.

$100.00Comparable value $100.00

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)

Dockers®

Truman Chelsea Boot (Men)

$59.97Current Price $59.97

(36% off)36% off.

$95.00Comparable value $95.00

(5)

New!

Ariat

Spitfire All Terrain Waterproof Chukka Boot (Men)

$89.97Current Price $89.97

(47% off)47% off.

$169.95Comparable value $169.95

(9)

New!

Clarks®

Wallaston Low Chukka Sneaker (Men)

$84.97Current Price $84.97

(22% off)22% off.

$110.00Comparable value $110.00

New!

Ariat

Spitfire Leather Chukka Boot (Men)

$59.97Current Price $59.97

(53% off)53% off.

$129.95Comparable value $129.95

(314)

New Markdown

NUNN BUSH

Delton Plain Toe Chelsea Boot (Men)

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

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

$95.00Comparable value $95.00

Eastland

Herman Water Resistant Chelsea Boot (Men)

$59.96 – $79.97Current Price $59.96 to $79.97

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

$135.00Comparable value $135.00

(2)

Eastland

Chimney Pond Chelsea Boot (Men)

$69.96 – $74.96Current Price $69.96 to $74.96

(Up to 51% off)Up to 51% off.

$145.00Comparable value $145.00

Cole Haan

Newmark Grand Chelsea Boot (Men)

$97.47Current Price $97.47

(72% off)72% off.

$360.00Comparable value $360.00

Florsheim

Azzano Plain Toe Chelsea Boot (Men)

$82.47Current Price $82.47

(43% off)43% off.

$145.00Comparable value $145.00

New!

Florsheim

Chalet Leather Cap Toe Boot (Men)

$109.97Current Price $109.97

(29% off)29% off.

$155.00Comparable value $155.00

(21)

Dockers®

Moc Toe Boot (Men)

$64.97Current Price $64.97

(31% off)31% off.

$95.00Comparable value $95.00

(4)

Clarks®

Maplewalk Moc Toe Boot (Men)

$79.97Current Price $79.97

(33% off)33% off.

$120.00Comparable value $120.00

(6)

Eastland

Patterson Cap Toe Chukka Boot (Men)

$44.96Current Price $44.96

(50% off)50% off.

$90.00Comparable value $90.00

Aquatalia

Edwin Weatherproof Lace-Up Boot (Men)

$149.99 – $155.98Current Price $149.99 to $155.98

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

$575.00Comparable value $575.00

Johnston & Murphy

Barrett Alpine Boot (Men)

$74.96Current Price $74.96

(59% off)59% off.

$185.00Comparable value $185.00

(14)

New Markdown

Cole Haan

Chamberlain Cap Toe Boot (Men)

$97.47Current Price $97.47

(68% off)68% off.

$310.00Comparable value $310.00

(1)

Johnston & Murphy

Barrett Water Resistant Boot (Men)

$64.98 – $74.96Current Price $64.98 to $74.96

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

$185.00Comparable value $185.00

(60)

Eastland

'Seneca' Moc Toe Boot (Men)

$59.98 – $74.96Current Price $59.98 to $74.96

(Up to 52% off)Up to 52% off.

$125.00Comparable value $125.00

Johnston & Murphy

Upton Chukka Boot (Men)

$49.99Current Price $49.99

(70% off)70% off.

$169.00Comparable value $169.00

(19)

New!

Ariat

Wexford Chelsea Boot (Men)

$99.97Current Price $99.97

(47% off)47% off.

$189.95Comparable value $189.95

New!

Johnston & Murphy

Upton Chelsea Boot (Men)

$129.97Current Price $129.97

(27% off)27% off.

$179.00Comparable value $179.00

(6)

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)

Florsheim

Forge Lace-Up Boot (Men)

$82.47Current Price $82.47

(38% off)38% off.

$135.00Comparable value $135.00

Ariat

Downtown Western Boot (Men)

$129.97Current Price $129.97

(50% off)50% off.

$259.95Comparable value $259.95

(19)

Only a few left

Eastland

Seth Memory Foam Chukka Boot (Men)

$44.96Current Price $44.96

(50% off)50% off.

$90.00Comparable value $90.00

(1)

Cole Haan

Chamberlin Grand Chelsea Boot (Men)

$97.47Current Price $97.47

(62% off)62% off.

$260.00Comparable value $260.00

(1)

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)

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

Dockers®

Dylan Chelsea Boot (Men)

$59.97Current Price $59.97

(36% off)36% off.

$95.00Comparable value $95.00

(5)

Clarks®

Wallaston Low Chukka Boot (Men)

$84.97Current Price $84.97

(22% off)22% off.

$110.00Comparable value $110.00