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Comfort Boots for Men

  • All Comfort
  • Boots
  • Dress Shoes
  • Loafers & Oxfords
  • Slippers
  • Sneakers
230 items
Uptown Western Boot (Men)
Ariat

Uptown Western Boot (Men)

$149.97Current Price $149.97
(40% off)40% off.
$249.95Comparable value $249.95
(12)
Only a few left
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
(80)
Azzano Plain Toe Chelsea Boot (Men)
New!
Florsheim

Azzano Plain Toe Chelsea Boot (Men)

$109.97Current Price $109.97
(24% off)24% off.
$145.00Comparable value $145.00
Chimney Pond Chelsea Boot (Men)
New!
Eastland

Chimney Pond Chelsea Boot (Men)

$99.97Current Price $99.97
(31% off)31% off.
$145.00Comparable value $145.00
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)
Chadwick Cap Toe Boot (Men)
Johnston & Murphy

Chadwick Cap Toe Boot (Men)

$89.97Current Price $89.97
(54% off)54% off.
$198.00Comparable value $198.00
(2)
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)
Hutson Plain Toe Boot (Men)
Johnston & Murphy

Hutson Plain Toe Boot (Men)

$99.97Current Price $99.97
(40% off)40% off.
$169.00Comparable value $169.00
(1)
Dax Waterproof Chelsea Boot (Men)
Bos. & Co.

Dax Waterproof Chelsea Boot (Men)

$124.97Current Price $124.97
(54% off)54% off.
$275.00Comparable value $275.00
(2)
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
Fortino Water Repellent Boot (Men)
New!
Aquatalia

Fortino Water Repellent Boot (Men)

$259.97Current Price $259.97
(58% off)58% off.
$625.00Comparable value $625.00
(1)
Cason Waterproof Wool Boot (Men)
Black Friday Deal
UGG®

Cason Waterproof Wool Boot (Men)

$119.97Current Price $119.97
(47% off)47% off.
$230.00Comparable value $230.00
(4)
Pix Combat Boot (Men)
Camper

Pix Combat Boot (Men)

$124.97Current Price $124.97
(35% off)35% off.
$195.00Comparable value $195.00
Brutus Combat Boot (Men)
Camper

Brutus Combat Boot (Men)

$129.97Current Price $129.97
(40% off)40% off.
$220.00Comparable value $220.00
Only a few left
Maplewalk Waterproof Boot (Men)
Clarks®

Maplewalk Waterproof Boot (Men)

$89.97Current Price $89.97
(25% off)25% off.
$120.00Comparable value $120.00
(4)
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
Field GoreTex® Waterproof Boot (Men)
Timberland

Field GoreTex® Waterproof Boot (Men)

$99.97Current Price $99.97
(54% off)54% off.
$220.00Comparable value $220.00
(2)
Patterson Cap Toe Chukka Boot (Men)
Eastland

Patterson Cap Toe Chukka Boot (Men)

$59.97Current Price $59.97
(33% off)33% off.
$90.00Comparable value $90.00
Recon Lace Boot (Men)
Ariat

Recon Lace Boot (Men)

$139.97Current Price $139.97
(12% off)12% off.
$159.95Comparable value $159.95
(101)
Steadwell Plain Toe Chukka Boot (Men)
Clarks®

Steadwell Plain Toe Chukka Boot (Men)

$79.97Current Price $79.97
(27% off)27% off.
$110.00Comparable value $110.00
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)
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
1912 Plain Toe Boot - Wide Width Available (Men)
NUNN BUSH

1912 Plain Toe Boot - Wide Width Available (Men)

$79.97Current Price $79.97
(27% off)27% off.
$110.00Comparable value $110.00
(6)
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)
Excavate Water Resistant Moc Toe Boot (Men)
NUNN BUSH

Excavate Water Resistant Moc Toe Boot (Men)

$69.97Current Price $69.97
(26% off)26% off.
$95.00Comparable value $95.00
(4)
Dylan Chelsea Boot (Men)
Dockers®

Dylan Chelsea Boot (Men)

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

Neumel Chelsea Boot (Men)

$89.97Current Price $89.97
(35% off)35% off.
$140.00Comparable value $140.00
(24)
Henson XC4 Waterproof Chukka Boot (Men)
Johnston & Murphy

Henson XC4 Waterproof Chukka Boot (Men)

$99.97 – $109.97Current Price $99.97 to $109.97
(Up to 49% off)Up to 49% off.
$199.00Comparable value $199.00
(16)
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)
Burleigh Chelsea Boot (Men)
Black Friday Deal
UGG®

Burleigh Chelsea Boot (Men)

$89.99Current Price $89.99
(47% off)47% off.
$170.00Comparable value $170.00
(8)
Delton Plain Toe Chukka Boot (Men)
NUNN BUSH

Delton Plain Toe Chukka Boot (Men)

$54.97Current Price $54.97
(42% off)42% off.
$95.00Comparable value $95.00
Britton Road Mid Gore-Tex® Waterproof Boot (Men)
Timberland

Britton Road Mid Gore-Tex® Waterproof Boot (Men)

$149.97Current Price $149.97
(42% off)42% off.
$260.00Comparable value $260.00
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)
Steadwell Dress Boot (Men)
New!
Clarks®

Steadwell Dress Boot (Men)

$99.97Current Price $99.97
(23% off)23% off.
$130.00Comparable value $130.00
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)
Edmundo Water Repellent Combat Boot (Men)
New!
Aquatalia

Edmundo Water Repellent Combat Boot (Men)

$259.97Current Price $259.97
(58% off)58% off.
$625.00Comparable value $625.00
(2)
Dean Chelsea Boot (Men)
New!
Camper

Dean Chelsea Boot (Men)

$149.97Current Price $149.97
(34% off)34% off.
$230.00Comparable value $230.00
Only a few left
Classic Mini Boot (Men)
Black Friday Deal
UGG®

Classic Mini Boot (Men)

$89.97Current Price $89.97
(43% off)43% off.
$160.00Comparable value $160.00
(3)
Grand Woodbury Waterproof Boot (Men)
Cole Haan

Grand Woodbury Waterproof Boot (Men)

$144.97Current Price $144.97
(42% off)42% off.
$250.00Comparable value $250.00
(2)
Bangor Chukka Boot
Deer Stags

Bangor Chukka Boot

$54.97Current Price $54.97
(45% off)45% off.
$100.00Comparable value $100.00
Newmarket Chukka Boot (Men)
Timberland

Newmarket Chukka Boot (Men)

$89.97Current Price $89.97
(40% off)40% off.
$150.00Comparable value $150.00
(5)
Treeline Lace-Up Waterproof Boot (Men)
Timberland

Treeline Lace-Up Waterproof Boot (Men)

$79.97Current Price $79.97
(42% off)42% off.
$140.00Comparable value $140.00
(18)
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)
Only a few left
Venture Daze Ultra Mini Boot (Men)
UGG®

Venture Daze Ultra Mini Boot (Men)

$99.97Current Price $99.97
(44% off)44% off.
$180.00Comparable value $180.00
(6)
Steadfast Western Boot (Men)
Ariat

Steadfast Western Boot (Men)

$99.97Current Price $99.97
(58% off)58% off.
$239.95Comparable value $239.95
(26)
Only a few left
Hugo Boot
Eastland

Hugo Boot

$59.97Current Price $59.97
(40% off)40% off.
$100.00Comparable value $100.00
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)
Charge Work Boot - Wide Width Available
Dr. Scholl's

Charge Work Boot - Wide Width Available

$84.97Current Price $84.97
(34% off)34% off.
$130.00Comparable value $130.00
(44)
Attleboro Mid Chukka Boot (Men)
New!
Timberland

Attleboro Mid Chukka Boot (Men)

$69.97Current Price $69.97
(46% off)46% off.
$130.00Comparable value $130.00
(4)
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
Ruvo Chelsea Boot (Men)
Florsheim

Ruvo Chelsea Boot (Men)

$109.97Current Price $109.97
(26% off)26% off.
$150.00Comparable value $150.00
(21)
Forge Chelsea Boot (Men)
New!
Florsheim

Forge Chelsea Boot (Men)

$109.97Current Price $109.97
(15% off)15% off.
$130.00Comparable value $130.00
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)
Butte Waterproof Boot (Men)
UGG®

Butte Waterproof Boot (Men)

$119.97Current Price $119.97
(50% off)50% off.
$240.00Comparable value $240.00
(198)
Denali Waterproof Plain Toe Boot - Wide Width Available
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)
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)
Only a few left
Truman Chelsea Boot (Men)
Dockers®

Truman Chelsea Boot (Men)

$59.97Current Price $59.97
(36% off)36% off.
$95.00Comparable value $95.00
(1)
Forge Lace-Up Boot (Men)
New!
Florsheim

Forge Lace-Up Boot (Men)

$109.97Current Price $109.97
(18% off)18% off.
$135.00Comparable value $135.00
Delton Plain Toe Chelsea Boot (Men)
NUNN BUSH

Delton Plain Toe Chelsea Boot (Men)

$54.97Current Price $54.97
(42% off)42% 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)
Saltwater Duck Toe Boot (Men)
New!
Sperry

Saltwater Duck Toe Boot (Men)

$39.97Current Price $39.97
(69% off)69% off.
$130.00Comparable value $130.00
(69)
Otis II Chelsea Boot (Men)
NUNN BUSH

Otis II Chelsea Boot (Men)

$94.97Current Price $94.97
(13% off)13% off.
$110.00Comparable value $110.00
(1)
Hybrid Rancher BOA® Waterproof Cowboy Boot (Men)
Ariat

Hybrid Rancher BOA® Waterproof Cowboy Boot (Men)

$119.97Current Price $119.97
(52% off)52% off.
$249.95Comparable value $249.95
(31)
Only a few left
Odell II Wingtip Boot (Men)
NUNN BUSH

Odell II Wingtip Boot (Men)

$94.97Current Price $94.97
(13% off)13% off.
$110.00Comparable value $110.00
(1)
Neumel Trailgazer Waterproof Boot (Men)
Black Friday Deal
UGG®

Neumel Trailgazer Waterproof Boot (Men)

$79.97Current Price $79.97
(55% off)55% off.
$180.00Comparable value $180.00
(1)
Telford Lace-Up Boot (Men)
Dockers®

Telford Lace-Up Boot (Men)

$59.97Current Price $59.97
(36% off)36% off.
$95.00Comparable value $95.00
Brutus Trek Waterproof Chelsea Boot (Men)
New!
Camper

Brutus Trek Waterproof Chelsea Boot (Men)

$164.97 – $169.97Current Price $164.97 to $169.97
(35% off)35% off.
$255.00 – $265.00Comparable value $255.00 to $265.00
(3)
Only a few left
Walpath Waterproof Chelsea Boot (Men)
New!
Clarks®

Walpath Waterproof Chelsea Boot (Men)

$99.97Current Price $99.97
(23% off)23% off.
$130.00Comparable value $130.00
Speed Solo Mid Waterproof Hiking Boot (Men)
Merrell

Speed Solo Mid Waterproof Hiking Boot (Men)

$94.97Current Price $94.97
(36% off)36% off.
$150.00Comparable value $150.00
(60)
Townsend Chelsea Boot (Men)
Dockers®

Townsend Chelsea Boot (Men)

$39.97Current Price $39.97
(57% off)57% off.
$95.00Comparable value $95.00
(1)
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