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Comfort Boots for Men

  • All Comfort
  • Boots
  • Dress Shoes
  • Loafers & Oxfords
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183 items
Chamberlin Grand Chelsea Boot (Men)
Cole Haan

Chamberlin Grand Chelsea Boot (Men)

$129.97Current Price $129.97
(50% off)50% off.
$260.00Comparable value $260.00
(1)
Karnak Water Resistant Moc Toe Boot (Men)
NUNN BUSH

Karnak Water Resistant Moc Toe Boot (Men)

$89.97Current Price $89.97
(18% off)18% off.
$110.00Comparable value $110.00
(3)
Azzano Plain Toe Chelsea Boot (Men)
Florsheim

Azzano Plain Toe Chelsea Boot (Men)

$109.97Current Price $109.97
(24% off)24% off.
$145.00Comparable value $145.00
Baxter Boot (Men)
Eastland

Baxter Boot (Men)

$69.97Current Price $69.97
(48% off)48% off.
$135.00Comparable value $135.00
Dylan Chelsea Boot (Men)
Dockers®

Dylan Chelsea Boot (Men)

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

Biltmore Waterproof Chelsea Boot (Men)

$109.97Current Price $109.97
(26% off)26% off.
$150.00Comparable value $150.00
(53)
Only a few left
Wallaston Low Chukka Boot (Men)
New!
Clarks®

Wallaston Low Chukka Boot (Men)

$84.97Current Price $84.97
(22% off)22% off.
$110.00Comparable value $110.00
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)
Hugo Boot
Eastland

Hugo Boot

$44.97 – $59.97Current Price $44.97 to $59.97
(Up to 55% off select items)Up to 55% off select items.
$100.00Comparable value $100.00
Newmarket Mid Lace Up Boot (Men)
Timberland

Newmarket Mid Lace Up Boot (Men)

$59.97Current Price $59.97
(60% off)60% off.
$150.00Comparable value $150.00
(4)
Grand Lug Sole Boot (Men)
Cole Haan

Grand Lug Sole Boot (Men)

$99.97Current Price $99.97
(25% off)25% off.
$135.00Comparable value $135.00
(2)
Excavate Plain Toe Boot - Wide Width Available (Men)
NUNN BUSH

Excavate Plain Toe Boot - Wide Width Available (Men)

$59.97 – $64.97Current Price $59.97 to $64.97
(Up to 36% off)Up to 36% off.
$90.00 – $95.00Comparable value $90.00 to $95.00
(4)
Townsend Chelsea Boot (Men)
Dockers®

Townsend Chelsea Boot (Men)

$39.97Current Price $39.97
(57% off)57% off.
$95.00Comparable value $95.00
(1)
Walpath Waterproof Chukka Boot (Men)
Clarks®

Walpath Waterproof Chukka Boot (Men)

$99.97Current Price $99.97
(23% off)23% off.
$130.00Comparable value $130.00
Moab 3 Vista Waterproof Mid Hiking Shoe (Men)
Merrell

Moab 3 Vista Waterproof Mid Hiking Shoe (Men)

$69.97Current Price $69.97
(53% off)53% off.
$150.00Comparable value $150.00
(42)
Dustin Boot (Men)
Dockers®

Dustin Boot (Men)

$59.97Current Price $59.97
(36% off)36% off.
$95.00Comparable value $95.00
Calgary Chukka Boot (Men)
Dockers®

Calgary Chukka Boot (Men)

$69.97Current Price $69.97
(26% off)26% off.
$95.00Comparable value $95.00
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
(17)
'Daily Double' Chelsea Boot (Men)
Eastland

'Daily Double' Chelsea Boot (Men)

$74.97Current Price $74.97
(40% off)40% off.
$125.00Comparable value $125.00
(8)
Attleboro Mid Chukka Boot (Men)
Timberland

Attleboro Mid Chukka Boot (Men)

$69.97Current Price $69.97
(46% off)46% off.
$130.00Comparable value $130.00
(5)
Camden Chelsea Boot (Men)
Dockers®

Camden Chelsea Boot (Men)

$59.99Current Price $59.99
(29% off)29% off.
$85.00Comparable value $85.00
Newmarket Chukka Boot (Men)
Timberland

Newmarket Chukka Boot (Men)

$89.97Current Price $89.97
(40% off)40% off.
$150.00Comparable value $150.00
(6)
Chamberlain Cap Toe Boot (Men)
Cole Haan

Chamberlain Cap Toe Boot (Men)

$129.97Current Price $129.97
(58% off)58% off.
$310.00Comparable value $310.00
(1)
Avenue Waterproof Duck Boot (Men)
Sperry

Avenue Waterproof Duck Boot (Men)

$39.97 – $49.97Current Price $39.97 to $49.97
(Up to 66% off)Up to 66% off.
$120.00Comparable value $120.00
(1)
x John Deere Relaxed Fit Terraform Waterproof Boot (Men)
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)
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
Patterson Cap Toe Chukka Boot (Men)
Eastland

Patterson Cap Toe Chukka Boot (Men)

$44.97Current Price $44.97
(50% off)50% off.
$90.00Comparable value $90.00
'Seneca' Moc Toe Boot (Men)
Eastland

'Seneca' Moc Toe Boot (Men)

$74.97Current Price $74.97
(40% off)40% off.
$125.00Comparable value $125.00
Cason Waterproof Wool Boot (Men)
UGG®

Cason Waterproof Wool Boot (Men)

$119.97Current Price $119.97
(47% off)47% off.
$230.00Comparable value $230.00
(5)
Only a few left
Belgrade Boot (Men)
Eastland

Belgrade Boot (Men)

$74.97Current Price $74.97
(46% off)46% off.
$140.00Comparable value $140.00
Avenue Duck Boot (Men)
Sperry

Avenue Duck Boot (Men)

$59.97Current Price $59.97
(50% off)50% off.
$120.00Comparable value $120.00
(16)
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)
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)
Heritage Western Boot (Men)
Ariat

Heritage Western Boot (Men)

$104.97Current Price $104.97
(44% off)44% off.
$189.95Comparable value $189.95
(347)
Hutson Plain Toe Boot (Men)
Johnston & Murphy

Hutson Plain Toe Boot (Men)

$74.97 – $99.97Current Price $74.97 to $99.97
(Up to 55% off select items)Up to 55% off select items.
$169.00Comparable value $169.00
(2)
Tobias Lug Sole Boot (Men)
Dockers®

Tobias Lug Sole Boot (Men)

$59.97Current Price $59.97
(36% off)36% off.
$95.00Comparable value $95.00
Clifton Waterproof Chelsea Duck Boot (Men)
New!
Sperry

Clifton Waterproof Chelsea Duck Boot (Men)

$49.97Current Price $49.97
(54% off)54% off.
$110.00Comparable value $110.00
Barnyard Twin Gore II Waterproof Boot (Men)
Ariat

Barnyard Twin Gore II Waterproof Boot (Men)

$99.97Current Price $99.97
(44% off)44% off.
$179.95Comparable value $179.95
(41)
Only a few left
Cold Bay Duck Boot (Men)
Sperry

Cold Bay Duck Boot (Men)

$39.97Current Price $39.97
(66% off)66% off.
$120.00Comparable value $120.00
(5)
Rockaway Waterproof Boot (Men)
Timberland

Rockaway Waterproof Boot (Men)

$89.97Current Price $89.97
(35% off)35% off.
$140.00Comparable value $140.00
Only a few left
Slingshot Western Boot (Men)
Ariat

Slingshot Western Boot (Men)

$149.97Current Price $149.97
(34% off)34% off.
$229.95Comparable value $229.95
(59)
Ethan 1955 Cap Toe Boot (Men)
Eastland

Ethan 1955 Cap Toe Boot (Men)

$99.99Current Price $99.99
(55% off)55% off.
$225.00Comparable value $225.00
Finn Plain Toe Boot (Men)
Eastland

Finn Plain Toe Boot (Men)

$44.97Current Price $44.97
(50% off)50% off.
$90.00Comparable value $90.00
(2)
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
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
Emmett Waterproof Snow Boot (Men)
UGG®

Emmett Waterproof Snow Boot (Men)

$79.97Current Price $79.97
(46% off)46% off.
$150.00Comparable value $150.00
(119)
Only a few left
Burleigh Chukka (Men)
New!
UGG®

Burleigh Chukka (Men)

$89.97Current Price $89.97
(43% off)43% off.
$160.00Comparable value $160.00
(15)
Only a few left
Westmore Chukka Boot (Men)
Timberland

Westmore Chukka Boot (Men)

$69.97Current Price $69.97
(36% off)36% off.
$110.00Comparable value $110.00
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
(45)
Moab 3 Mid Waterproof Hiking Shoe (Men)
Merrell

Moab 3 Mid Waterproof Hiking Shoe (Men)

$99.97Current Price $99.97
(41% off)41% off.
$170.00Comparable value $170.00
(363)
Brutus Combat Boot (Men)
Camper

Brutus Combat Boot (Men)

$129.97 – $139.97Current Price $129.97 to $139.97
(Up to 40% off)Up to 40% off.
$220.00Comparable value $220.00
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
1912 Plain Toe Chelsea Boot (Men)
NUNN BUSH

1912 Plain Toe Chelsea Boot (Men)

$79.97Current Price $79.97
(27% off)27% off.
$110.00Comparable value $110.00
(2)
Futurity Cashout Square Toe Boot (Men)
Ariat

Futurity Cashout Square Toe Boot (Men)

$169.97Current Price $169.97
(39% off)39% off.
$279.95Comparable value $279.95
(9)
Only a few left
Recon Lace Boot (Men)
Ariat

Recon Lace Boot (Men)

$139.97Current Price $139.97
(12% off)12% off.
$159.95Comparable value $159.95
(101)
Neumel Boot (Men)
UGG®

Neumel Boot (Men)

$109.97Current Price $109.97
(26% off)26% off.
$150.00Comparable value $150.00
(7)
Euro Spring Mid Hiking Boot (Men)
New!
Timberland

Euro Spring Mid Hiking Boot (Men)

$69.97Current Price $69.97
(46% off)46% off.
$130.00Comparable value $130.00
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)
Only a few left
x John Deere Segment 2.0 Waterproof Chelsea Boot (Men)
SKECHERS

x John Deere Segment 2.0 Waterproof Chelsea Boot (Men)

$59.97Current Price $59.97
(53% off)53% off.
$128.00Comparable value $128.00
(4)
Sting Western Boot (Men)
Ariat

Sting Western Boot (Men)

$179.97Current Price $179.97
(33% off)33% off.
$269.95Comparable value $269.95
(55)
Lewis Chelsea Boot (Men)
Johnston & Murphy

Lewis Chelsea Boot (Men)

$69.97Current Price $69.97
(45% off)45% off.
$129.00Comparable value $129.00
(5)
Lewis Side Zip Boot (Men)
Johnston & Murphy

Lewis Side Zip Boot (Men)

$69.97Current Price $69.97
(45% off)45% off.
$129.00Comparable value $129.00
(39)
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
Futurity Cashout Square Toe Boot (Men)
Ariat

Futurity Cashout Square Toe Boot (Men)

$169.97Current Price $169.97
(39% off)39% off.
$279.95Comparable value $279.95
(6)
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)
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
Cold Bay Duck Boot (Men)
Sperry

Cold Bay Duck Boot (Men)

$49.97Current Price $49.97
(61% off)61% off.
$130.00Comparable value $130.00
(22)
Float Waterproof Rain Boot (Men)
Sperry

Float Waterproof Rain Boot (Men)

$39.97Current Price $39.97
(57% off)57% off.
$95.00Comparable value $95.00
(7)
Trekker Mid Sneaker (Men)
NUNN BUSH

Trekker Mid Sneaker (Men)

$39.97Current Price $39.97
(52% off)52% off.
$85.00Comparable value $85.00
(2)
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)
Only a few left
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
Brody Chukka Boot (Men)
Johnston & Murphy

Brody Chukka Boot (Men)

$109.97Current Price $109.97
(33% off)33% off.
$165.00Comparable value $165.00
(27)
Only a few left
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