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Comfort Boots for Men

  • All Comfort
  • Boots
  • Dress Shoes
  • Loafers & Oxfords
  • Slippers
  • Sneakers
219 items
Thomson Chukka Boot (Men)
Børn

Thomson Chukka Boot (Men)

$89.97Current Price $89.97
(30% off)30% off.
$130.00Comparable value $130.00
(25)
Grand Remix Chukka Boot (Men)
New!
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
(12)
Booker Chelsea Round Toe Boot (Men)
New!
Ariat

Booker Chelsea Round Toe Boot (Men)

$79.97Current Price $79.97
(46% off)46% off.
$149.95Comparable value $149.95
(138)
Only a few left
Karnak Plain Toe Chelsea Boot (Men)
NUNN BUSH

Karnak Plain Toe Chelsea Boot (Men)

$89.97Current Price $89.97
(25% off)25% off.
$120.00Comparable value $120.00
Spitfire All Terrain Waterproof Chukka Boot (Men)
New!
Ariat

Spitfire All Terrain Waterproof Chukka Boot (Men)

$89.97Current Price $89.97
(47% off)47% off.
$169.95Comparable value $169.95
(2)
2.Zerogrand Chukka Boot (Men)
Cole Haan

2.Zerogrand Chukka Boot (Men)

$99.97Current Price $99.97
(70% off)70% off.
$338.00Comparable value $338.00
(388)
Theo Chukka Boot (Men)
New!
Børn

Theo Chukka Boot (Men)

$79.97Current Price $79.97
(38% off)38% off.
$130.00Comparable value $130.00
(5)
Sport Stratten Leather Boot (Men)
Ariat

Sport Stratten Leather Boot (Men)

$99.97Current Price $99.97
(47% off)47% off.
$189.95Comparable value $189.95
(50)
Only a few left
Otto Chukka Boot - Wide Width Available (Men)
NUNN BUSH

Otto Chukka Boot - Wide Width Available (Men)

$44.97 – $74.97Current Price $44.97 to $74.97
(Up to 52% off)Up to 52% off.
$95.00Comparable value $95.00
(11)
Stump Jumper Boot (Men)
Ariat

Stump Jumper Boot (Men)

$119.97Current Price $119.97
(40% off)40% off.
$199.95Comparable value $199.95
(24)
Only a few left
Wallaston Chukka Boot (Men)
New!
Clarks®

Wallaston Chukka Boot (Men)

$79.97Current Price $79.97
(33% off)33% off.
$120.00Comparable value $120.00
Burleigh Chukka (Men)
Black Friday Deal
UGG®

Burleigh Chukka (Men)

$89.97Current Price $89.97
(43% off)43% off.
$160.00Comparable value $160.00
(10)
Morse GRANDFØAM Chukka Boot (Men)
New!
Cole Haan

Morse GRANDFØAM Chukka Boot (Men)

$109.97Current Price $109.97
(51% off)51% off.
$228.00Comparable value $228.00
Maplewalk Rise Boot (Men)
New!
Clarks®

Maplewalk Rise Boot (Men)

$89.97Current Price $89.97
(25% off)25% off.
$120.00Comparable value $120.00
Spitfire Leather Chukka Boot (Men)
New!
Ariat

Spitfire Leather Chukka Boot (Men)

$59.97Current Price $59.97
(53% off)53% off.
$129.95Comparable value $129.95
(298)
Only a few left
x John Deere Relaxed Fit Terraform Waterproof Boot (Men)
New!
SKECHERS

x John Deere Relaxed Fit Terraform Waterproof Boot (Men)

$59.97Current Price $59.97
(55% off)55% off.
$135.00Comparable value $135.00
(9)
Trekker Mid Sneaker (Men)
NUNN BUSH

Trekker Mid Sneaker (Men)

$54.97Current Price $54.97
(35% off)35% off.
$85.00Comparable value $85.00
(2)
'Lookout' Moc Toe Boot (Men)
Ariat

'Lookout' Moc Toe Boot (Men)

$79.97Current Price $79.97
(50% off)50% off.
$159.95Comparable value $159.95
(66)
Only a few left
Chase Plain Toe Chukka Boot - Wide Width Available (Men)
NUNN BUSH

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

$44.97 – $54.97Current Price $44.97 to $54.97
(Up to 52% off)Up to 52% off.
$90.00 – $95.00Comparable value $90.00 to $95.00
(10)
Avenue Waterproof Duck Boot (Men)
New!
Sperry

Avenue Waterproof Duck Boot (Men)

$39.97Current Price $39.97
(66% off)66% off.
$120.00Comparable value $120.00
(1)
Dakoda Chelsea Boot (Men)
NUNN BUSH

Dakoda Chelsea Boot (Men)

$44.97 – $54.97Current Price $44.97 to $54.97
(Up to 52% off)Up to 52% off.
$95.00Comparable value $95.00
(24)
Craftwell Lace-Up Boot (Men)
Clarks®

Craftwell Lace-Up Boot (Men)

$79.97Current Price $79.97
(27% off)27% off.
$110.00Comparable value $110.00
Eli Suede Chukka Boot (Men)
Børn

Eli Suede Chukka Boot (Men)

$89.97Current Price $89.97
(30% off)30% off.
$130.00Comparable value $130.00
(1)
The UGG Lug Waterproof Chukka Boot (Men)
Black Friday Deal
UGG®

The UGG Lug Waterproof Chukka Boot (Men)

$79.97Current Price $79.97
(38% off)38% off.
$130.00Comparable value $130.00
Chamberlin Grand Chukka Boot (Men)
New!
Cole Haan

Chamberlin Grand Chukka Boot (Men)

$129.97Current Price $129.97
(55% off)55% off.
$290.00Comparable value $290.00
(1)
Walpath Waterproof Chukka Boot (Men)
New!
Clarks®

Walpath Waterproof Chukka Boot (Men)

$99.97Current Price $99.97
(23% off)23% off.
$130.00Comparable value $130.00
Emmett Chelsea Boot (Men)
Clarks®

Emmett Chelsea Boot (Men)

$79.97 – $89.97Current Price $79.97 to $89.97
(Up to 27% off)Up to 27% off.
$110.00 – $120.00Comparable value $110.00 to $120.00
Weltridge Side Zip Boot (Men)
New!
Clarks®

Weltridge Side Zip Boot (Men)

$94.97Current Price $94.97
(26% off)26% off.
$130.00Comparable value $130.00
Field Trekker Waterproof Boot (Men)
Timberland

Field Trekker Waterproof Boot (Men)

$69.97Current Price $69.97
(36% off)36% off.
$110.00Comparable value $110.00
(3)
Herman Water Resistant Chelsea Boot (Men)
Eastland

Herman Water Resistant Chelsea Boot (Men)

$79.97Current Price $79.97
(40% off)40% off.
$135.00Comparable value $135.00
(2)
Garfield Plain Toe Chukka Boot (Men)
Deer Stags

Garfield Plain Toe Chukka Boot (Men)

$64.97Current Price $64.97
(35% off)35% off.
$100.00Comparable value $100.00
Gender Inclusive Campfire Crafted Regenerate Water Resistant Boot
UGG®

Gender Inclusive Campfire Crafted Regenerate Water Resistant Boot

$109.97Current Price $109.97
(50% off)50% off.
$220.00Comparable value $220.00
(2)
Seth Memory Foam Chukka Boot (Men)
Eastland

Seth Memory Foam Chukka Boot (Men)

$59.97Current Price $59.97
(33% off)33% off.
$90.00Comparable value $90.00
(1)
Attleboro Chelsea Boot (Men)
New!
Timberland

Attleboro Chelsea Boot (Men)

$69.97 – $74.97Current Price $69.97 to $74.97
(46% off)46% off.
$130.00 – $140.00Comparable value $130.00 to $140.00
(3)
Newmarket Chukka Boot (Men)
Timberland

Newmarket Chukka Boot (Men)

$89.97Current Price $89.97
(40% off)40% off.
$150.00Comparable value $150.00
(5)
Circuit Plain Toe Chukka Boot - Wide Width Available (Men)
NUNN BUSH

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

$54.97Current Price $54.97
(38% off)38% off.
$90.00Comparable value $90.00
(16)
Spitfire Leather Chukka Boot (Men)
New!
Ariat

Spitfire Leather Chukka Boot (Men)

$69.97Current Price $69.97
(50% off)50% off.
$139.95Comparable value $139.95
(41)
'Mesteno' Boot (Men)
Ariat

'Mesteno' Boot (Men)

$149.97Current Price $149.97
(44% off)44% off.
$269.95Comparable value $269.95
(48)
Only a few left
Boswell Chukka Boot (Men)
Johnston & Murphy

Boswell Chukka Boot (Men)

$89.97Current Price $89.97
(48% off)48% off.
$175.00Comparable value $175.00
(4)
Esmond Plain Toe Chukka Boot (Men)
Black Friday Deal
Dockers®

Esmond Plain Toe Chukka Boot (Men)

$39.97 – $54.99Current Price $39.97 to $54.99
(Up to 57% off)Up to 57% off.
$85.00 – $95.00Comparable value $85.00 to $95.00
(5)
Shepton Chukka Boot (Men)
Clarks®

Shepton Chukka Boot (Men)

$74.97Current Price $74.97
(Up to 31% off)Up to 31% off.
$100.00 – $110.00Comparable value $100.00 to $110.00
(1)
Shepton Chukka Boot (Men)
Clarks®

Shepton Chukka Boot (Men)

$74.97Current Price $74.97
(31% off)31% off.
$110.00Comparable value $110.00
Shepton Easy Chelsea Boot (Men)
Clarks®

Shepton Easy Chelsea Boot (Men)

$94.97Current Price $94.97
(26% off)26% off.
$130.00Comparable value $130.00
Dee Chukka Boot (Men)
Dockers®

Dee Chukka Boot (Men)

$39.97Current Price $39.97
(57% off)57% off.
$95.00Comparable value $95.00
Venture Daze Ultra Mini Boot (Men)
Black Friday Deal
UGG®

Venture Daze Ultra Mini Boot (Men)

$92.99Current Price $92.99
(48% off)48% off.
$180.00Comparable value $180.00
(9)
Tempo Sol Mid Top Hiking Boot (Men)
Merrell

Tempo Sol Mid Top Hiking Boot (Men)

$79.97Current Price $79.97
(20% off)20% off.
$100.00Comparable value $100.00
(10)
Chamberlin Grand Water Resistant Chelsea Boot (Men)
New!
Cole Haan

Chamberlin Grand Water Resistant Chelsea Boot (Men)

$129.97Current Price $129.97
(50% off)50% off.
$260.00Comparable value $260.00
Rebar Wedge 6-Inch Waterproof Work Boot (Men)
Ariat

Rebar Wedge 6-Inch Waterproof Work Boot (Men)

$69.97Current Price $69.97
(56% off)56% off.
$159.95Comparable value $159.95
(30)
Grand Atlantic Chelsea Boot (Men)
New!
Cole Haan

Grand Atlantic Chelsea Boot (Men)

$99.97Current Price $99.97
(50% off)50% off.
$200.00Comparable value $200.00
(2)
Neumel Shaggy Suede Chukka Boot (Men)
UGG®

Neumel Shaggy Suede Chukka Boot (Men)

$89.97 – $94.97Current Price $89.97 to $94.97
(Up to 40% off)Up to 40% off.
$150.00Comparable value $150.00
(1)
Cryus Chelsea Boot (Men)
Eastland

Cryus Chelsea Boot (Men)

$59.97Current Price $59.97
(33% off)33% off.
$90.00Comparable value $90.00
(10)
Carlsbad Western Boot (Men)
Ariat

Carlsbad Western Boot (Men)

$149.97Current Price $149.97
(50% off)50% off.
$299.95Comparable value $299.95
(30)
Only a few left
Neumal Crafted Regenerate Water Resistant Chukka Boot (Men)
UGG®

Neumal Crafted Regenerate Water Resistant Chukka Boot (Men)

$99.97Current Price $99.97
(50% off)50% off.
$200.00Comparable value $200.00
(2)
Nalukai Kala Moc Toe Boot (Men)
OluKai

Nalukai Kala Moc Toe Boot (Men)

$69.97Current Price $69.97
(50% off)50% off.
$140.00Comparable value $140.00
(1)
Townsend Chelsea Boot (Men)
Dockers®

Townsend Chelsea Boot (Men)

$39.97Current Price $39.97
(57% off)57% off.
$95.00Comparable value $95.00
(1)
Farmland Waterproof Boot (Men)
Ariat

Farmland Waterproof Boot (Men)

$104.97Current Price $104.97
(19% off)19% off.
$129.95Comparable value $129.95
(33)
Only a few left
Radcliff Plain Toe Chukka Boot (Men)
Clarks®

Radcliff Plain Toe Chukka Boot (Men)

$89.97Current Price $89.97
(25% off)25% off.
$120.00Comparable value $120.00
(1)
Chalet Chelsea Boot (Men)
Florsheim

Chalet Chelsea Boot (Men)

$99.97Current Price $99.97
(31% off)31% off.
$145.00Comparable value $145.00
(108)
Zionic Waterproof Hiking Boot (Men)
KEEN

Zionic Waterproof Hiking Boot (Men)

$94.97Current Price $94.97
(44% off)44% off.
$170.00Comparable value $170.00
(2)
Camden Chelsea Boot (Men)
New!
Dockers®

Camden Chelsea Boot (Men)

$59.99Current Price $59.99
(29% off)29% off.
$85.00Comparable value $85.00
Hayden Chukka Boot (Men)
Black Friday Deal
UGG®

Hayden Chukka Boot (Men)

$79.99 – $109.97Current Price $79.99 to $109.97
(Up to 46% off select items)Up to 46% off select items.
$150.00Comparable value $150.00
(5)
Futurity Time Western Boot (Men)
Ariat

Futurity Time Western Boot (Men)

$149.97Current Price $149.97
(46% off)46% off.
$279.95Comparable value $279.95
(65)
Dylan Chelsea Boot (Men)
Dockers®

Dylan Chelsea Boot (Men)

$59.97Current Price $59.97
(36% off)36% off.
$95.00Comparable value $95.00
Neumel Waterproof Hybrid Boot (Men)
UGG®

Neumel Waterproof Hybrid Boot (Men)

$119.97Current Price $119.97
(36% off)36% off.
$190.00Comparable value $190.00
(5)
Moresby Waterproof Boot (Men)
Ariat

Moresby Waterproof Boot (Men)

$119.97Current Price $119.97
(42% off)42% off.
$209.95Comparable value $209.95
(22)
Only a few left
Pasquale Waterproof Boot (Men)
ara

Pasquale Waterproof Boot (Men)

$109.97Current Price $109.97
(54% off)54% off.
$240.00Comparable value $240.00
Chamberlin Grand Chelsea Boot (Men)
New!
Cole Haan

Chamberlin Grand Chelsea Boot (Men)

$129.97Current Price $129.97
(50% off)50% off.
$260.00Comparable value $260.00
Willie French Toe Western Boot (Men)
Ariat

Willie French Toe Western Boot (Men)

$149.97Current Price $149.97
(40% off)40% off.
$249.95Comparable value $249.95
(5)
Newmarket Mid Lace Up Boot (Men)
Timberland

Newmarket Mid Lace Up Boot (Men)

$79.97Current Price $79.97
(46% off)46% off.
$150.00Comparable value $150.00
(4)
Sport Patriot Cowboy Boot (Men)
Ariat

Sport Patriot Cowboy Boot (Men)

$99.97Current Price $99.97
(41% off)41% off.
$169.95Comparable value $169.95
(289)
Brody Chelsea Boot (Men)
Johnston & Murphy

Brody Chelsea Boot (Men)

$69.97Current Price $69.97
(57% off)57% off.
$165.00Comparable value $165.00
(18)
Emmett Waterproof Snow Boot (Men)
Black Friday Deal
UGG®

Emmett Waterproof Snow Boot (Men)

$64.99Current Price $64.99
(56% off)56% off.
$150.00Comparable value $150.00
(83)
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