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Comfort Boots for Men

  • All Comfort
  • Boots
  • Dress Shoes
  • Loafers & Oxfords
  • Sneakers
149 items
Judson Grand Chelsea Boot (Men)
New
Cole Haan

Judson Grand Chelsea Boot (Men)

$69.96Current Price $69.96
(73% off)73% off.
$260.00Comparable value $260.00
(13)
Only a few left
Bend Chelsea Boot (Men)
Birkenstock

Bend Chelsea Boot (Men)

$64.98Current Price $64.98
(61% off)61% off.
$170.00Comparable value $170.00
(2)
Judson Grand Chelsea Boot (Men)
New
Cole Haan

Judson Grand Chelsea Boot (Men)

$69.96Current Price $69.96
(73% off)73% off.
$260.00Comparable value $260.00
(16)
Only a few left
Chalet Chelsea Boot (Men)
Florsheim

Chalet Chelsea Boot (Men)

$69.96Current Price $69.96
(51% off)51% off.
$145.00Comparable value $145.00
(124)
Lockhart Mini Lug Suede Chelsea Boot (Men)
Nordstrom

Lockhart Mini Lug Suede Chelsea Boot (Men)

$32.48Current Price $32.48
(72% off)72% off.
$119.95Comparable value $119.95
(3)
Chalet Leather Cap Toe Boot (Men)
Florsheim

Chalet Leather Cap Toe Boot (Men)

$59.98Current Price $59.98
(61% off)61% off.
$155.00Comparable value $155.00
(25)
Metropole London Waterproof Suede Chukka Boot (Men)
New
ECCO

Metropole London Waterproof Suede Chukka Boot (Men)

$62.96Current Price $62.96
(72% off)72% off.
$229.95Previous Price $229.95
(3)
Shepton Chukka Boot (Men)
Clarks®

Shepton Chukka Boot (Men)

$48.73 – $74.97Current Price $48.73 to $74.97
(Up to 55% off select items)Up to 55% off select items.
$100.00 – $110.00Comparable value $100.00 to $110.00
(6)
Chase Plain Toe Chukka Boot - Wide Width Available (Men)
NUNN BUSH

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

$49.97Current Price $49.97
(47% off)47% off.
$95.00Comparable value $95.00
(14)
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)
Maplewalk Moc Toe Boot (Men)
Clarks®

Maplewalk Moc Toe Boot (Men)

$79.97Current Price $79.97
(33% off)33% off.
$120.00Comparable value $120.00
(6)
Lite Hybrid Chukka Boot (Men)
ECCO

Lite Hybrid Chukka Boot (Men)

$79.97Current Price $79.97
(42% off)42% off.
$140.00Comparable value $140.00
(1)
Karnak Water Resistant Moc Toe Boot - Wide Width Available (Men)
NUNN BUSH

Karnak Water Resistant Moc Toe Boot - Wide Width Available (Men)

$89.97Current Price $89.97
(Up to 25% off)Up to 25% off.
$110.00 – $120.00Comparable value $110.00 to $120.00
(3)
Highwood Chelsea Boot (Men)
New
Birkenstock

Highwood Chelsea Boot (Men)

$56.96Current Price $56.96
(72% off)72% off.
$210.00Previous Price $210.00
(3)
Only a few left
Metropole Milan Chukka Boot (Men) (Nordstrom Exclusive)
New
ECCO

Metropole Milan Chukka Boot (Men) (Nordstrom Exclusive)

$49.96Current Price $49.96
(74% off)74% off.
$194.95Previous Price $194.95
Only a few left
Headout Waterproof Mid Hiking Shoe (Men)
New
KEEN

Headout Waterproof Mid Hiking Shoe (Men)

$79.97Current Price $79.97
(46% off)46% off.
$150.00Comparable value $150.00
(1)
Tempo Sol Waterproof Hiking Boot (Men)
Merrell

Tempo Sol Waterproof Hiking Boot (Men)

$59.97Current Price $59.97
(25% off)25% off.
$80.00Comparable value $80.00
(2)
Speed Strike 2 Waterproof Hiking Boot (Men)
New
Merrell

Speed Strike 2 Waterproof Hiking Boot (Men)

Add to Bag or Wish List to see price(21)
Stuart Chukka (Men)
New
Josef Seibel

Stuart Chukka (Men)

$69.97Current Price $69.97
(61% off)61% off.
$180.00Comparable value $180.00
Boswell Chukka Boot (Men)
Johnston & Murphy

Boswell Chukka Boot (Men)

$49.98Current Price $49.98
(71% off)71% off.
$175.00Comparable value $175.00
(24)
Newford Chukka Boot (Men)
New
Clarks®

Newford Chukka Boot (Men)

$79.97Current Price $79.97
(38% off)38% off.
$130.00Comparable value $130.00
Moab Speed 2 Waterproof Hiking Boot (Men)
Merrell

Moab Speed 2 Waterproof Hiking Boot (Men)

$109.97Current Price $109.97
(42% off)42% off.
$190.00Comparable value $190.00
(33)
Conrad Waterproof Hiking Boot (Men)
New
Propét

Conrad Waterproof Hiking Boot (Men)

$59.97Current Price $59.97
(57% off)57% off.
$139.99Comparable value $139.99
Attleboro Mid Chukka Boot (Men)
Timberland

Attleboro Mid Chukka Boot (Men)

$49.99Current Price $49.99
(61% off)61% off.
$130.00Comparable value $130.00
(5)
Sport Rider Cowboy Boot (Men)
New
Ariat

Sport Rider Cowboy Boot (Men)

$99.97Current Price $99.97
(50% off)50% off.
$199.95Comparable value $199.95
(9)
Upton Chukka (Men)
Johnston & Murphy

Upton Chukka (Men)

$129.97Current Price $129.97
(27% off)27% off.
$179.00Comparable value $179.00
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
Upton Chelsea Boot (Men)
Johnston & Murphy

Upton Chelsea Boot (Men)

$129.97Current Price $129.97
(27% off)27% off.
$179.00Comparable value $179.00
(7)
Otto Chukka Boot - Wide Width Available (Men)
NUNN BUSH

Otto Chukka Boot - Wide Width Available (Men)

$49.97 – $79.97Current Price $49.97 to $79.97
(Up to 58% off)Up to 58% off.
$110.00 – $120.00Comparable value $110.00 to $120.00
(14)
Excavate Plain Toe Boot - Wide Width Available (Men)
NUNN BUSH

Excavate Plain Toe Boot - Wide Width Available (Men)

$64.97Current Price $64.97
(Up to 31% off)Up to 31% off.
$90.00 – $95.00Comparable value $90.00 to $95.00
(4)
'Targhee II' Waterproof Boot (Men)
New
KEEN

'Targhee II' Waterproof Boot (Men)

$89.97Current Price $89.97
(47% off)47% off.
$170.00Comparable value $170.00
(457)
Downtown Western Boot (Men)
Ariat

Downtown Western Boot (Men)

$139.97Current Price $139.97
(46% off)46% off.
$259.95Comparable value $259.95
(22)
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
Barrett Almond Toe Boot (Men)
Ariat

Barrett Almond Toe Boot (Men)

$159.97Current Price $159.97
(38% off)38% off.
$259.95Comparable value $259.95
(8)
Gore-Tex® Waterproof Desert Boot (Men)
New
Clarks® Originals

Gore-Tex® Waterproof Desert Boot (Men)

$89.97Current Price $89.97
(62% off)62% off.
$240.00Comparable value $240.00
Spitfire Leather Chukka Boot (Men)
Ariat

Spitfire Leather Chukka Boot (Men)

$69.97Current Price $69.97
(50% off)50% off.
$139.95Comparable value $139.95
(58)
Ozark II Chukka Boot - Wide Width Available (Men)
NUNN BUSH

Ozark II Chukka Boot - Wide Width Available (Men)

$89.97Current Price $89.97
(18% off)18% off.
$110.00Comparable value $110.00
(3)
Thomas Lace-Up Boot (Men)
Dockers®

Thomas Lace-Up Boot (Men)

$59.97Current Price $59.97
(36% off)36% off.
$95.00Comparable value $95.00
(6)
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
(5)
Wiley Cowboy Boot (Men)
New
Ariat

Wiley Cowboy Boot (Men)

$129.97Current Price $129.97
(51% off)51% off.
$269.95Comparable value $269.95
(32)
Moc Toe Boot (Men)
Dockers®

Moc Toe Boot (Men)

$64.97Current Price $64.97
(31% off)31% off.
$95.00Comparable value $95.00
(6)
Truman Chelsea Boot (Men)
Dockers®

Truman Chelsea Boot (Men)

$59.97Current Price $59.97
(36% off)36% off.
$95.00Comparable value $95.00
(5)
Wexford Chelsea Boot (Men)
Ariat

Wexford Chelsea Boot (Men)

$99.97Current Price $99.97
(47% off)47% off.
$189.95Comparable value $189.95
(4)
Odell II Wingtip Boot - Wide Width Available (Men)
NUNN BUSH

Odell II Wingtip Boot - Wide Width Available (Men)

$89.97Current Price $89.97
(18% off)18% off.
$110.00Comparable value $110.00
(4)
Wallabee 2 Future Chukka (Men)
New
Clarks®

Wallabee 2 Future Chukka (Men)

$69.97Current Price $69.97
(41% off)41% off.
$120.00Comparable value $120.00
Oakwood Cowboy Boot (Men)
Ariat

Oakwood Cowboy Boot (Men)

$129.97Current Price $129.97
(50% off)50% off.
$259.95Comparable value $259.95
(83)
Downtown Western Boot (Men)
Ariat

Downtown Western Boot (Men)

$139.97Current Price $139.97
(46% off)46% off.
$259.95Comparable value $259.95
(26)
Sting Western Boot (Men)
Ariat

Sting Western Boot (Men)

$149.97Current Price $149.97
(46% off)46% off.
$279.95Comparable value $279.95
(97)
Wallabee Gore-Tex® Waterproof Shoe (Men)
New
Clarks® Originals

Wallabee Gore-Tex® Waterproof Shoe (Men)

$119.97Current Price $119.97
(50% off)50% off.
$240.00Comparable value $240.00
Spitfire All Terrain Waterproof Chukka Boot (Men)
Ariat

Spitfire All Terrain Waterproof Chukka Boot (Men)

$89.97Current Price $89.97
(47% off)47% off.
$169.95Comparable value $169.95
(12)
Wallaston Low Chukka Sneaker (Men)
Clarks®

Wallaston Low Chukka Sneaker (Men)

$84.97Current Price $84.97
(22% off)22% off.
$110.00Comparable value $110.00
Sport Latigo Square Toe Roper Heel Boot (Men)
Ariat

Sport Latigo Square Toe Roper Heel Boot (Men)

$89.96Current Price $89.96
(47% off)47% off.
$169.95Comparable value $169.95
(31)
Only a few left
Grand Remix Chukka Boot (Men)
Cole Haan

Grand Remix Chukka Boot (Men)

$99.97Current Price $99.97
(54% off)54% off.
$220.00Comparable value $220.00
(15)
Only a few left
Desert Boot (Men)
New
Clarks® Originals

Desert Boot (Men)

$79.97Current Price $79.97
(50% off)50% off.
$160.00Comparable value $160.00
Speed Solo Mid Waterproof Hiking Boot (Men)
Merrell

Speed Solo Mid Waterproof Hiking Boot (Men)

$94.97Current Price $94.97
(40% off)40% off.
$160.00Comparable value $160.00
(6)
Esmond Chukka Boot (Men)
Dockers®

Esmond Chukka Boot (Men)

$59.97Current Price $59.97
(36% off)36% off.
$95.00Comparable value $95.00
(5)
Esmond Plain Toe Chukka Boot (Men)
Dockers®

Esmond Plain Toe Chukka Boot (Men)

$59.97Current Price $59.97
(29% off)29% off.
$85.00Comparable value $85.00
(10)
Avenue Duck Boot (Men)
Sperry

Avenue Duck Boot (Men)

$49.97Current Price $49.97
(58% off)58% off.
$120.00Comparable value $120.00
(26)
Premium 6-Inch Waterproof Boot (Men)
Timberland

Premium 6-Inch Waterproof Boot (Men)

$99.97Current Price $99.97
(52% off)52% off.
$210.00Comparable value $210.00
(2736)
Desert Boot (Men)
New
Clarks® Originals

Desert Boot (Men)

$79.97Current Price $79.97
(57% off)57% off.
$190.00Comparable value $190.00
Chelsea Lug Boot (Men)
New
UGG®

Chelsea Lug Boot (Men)

$99.97Current Price $99.97
(39% off)39% off.
$165.00Comparable value $165.00
(3)
Neumel High Top Waterproof Hybrid Boot (Men)
New
UGG®

Neumel High Top Waterproof Hybrid Boot (Men)

$129.97Current Price $129.97
(40% off)40% off.
$220.00Comparable value $220.00
(2)
Only a few left
Karnak Water Resistant Plain Toe Boot - Wide Width Available (Men)
NUNN BUSH

Karnak Water Resistant Plain Toe Boot - Wide Width Available (Men)

$89.97Current Price $89.97
(18% off)18% off.
$110.00Comparable value $110.00
Ridgeback Oily Western Boot (Men)
Ariat

Ridgeback Oily Western Boot (Men)

$129.97Current Price $129.97
(40% off)40% off.
$219.95Comparable value $219.95
(38)
Only a few left
Spitfire Leather Chukka Boot (Men)
Ariat

Spitfire Leather Chukka Boot (Men)

$59.97Current Price $59.97
(53% off)53% off.
$129.95Comparable value $129.95
(341)
Only a few left
x John Deere Lace-Up Boot (Men)
SKECHERS

x John Deere Lace-Up Boot (Men)

$59.97Current Price $59.97
(55% off)55% off.
$135.00Comparable value $135.00
Arcata Boot (Men)
New
Bogs

Arcata Boot (Men)

$119.97Current Price $119.97
(33% off)33% off.
$180.00Comparable value $180.00
(49)
Otis II Chelsea Boot - Wide Width Available (Men)
NUNN BUSH

Otis II Chelsea Boot - Wide Width Available (Men)

$89.97Current Price $89.97
(18% off)18% off.
$110.00Comparable value $110.00
(1)
Bodie Cowboy Boot (Men)
Ariat

Bodie Cowboy Boot (Men)

$99.97Current Price $99.97
(44% off)44% off.
$179.95Comparable value $179.95
(20)
Karnak Plain Toe Chelsea Boot - Wide Width Available (Men)
NUNN BUSH

Karnak Plain Toe Chelsea Boot - Wide Width Available (Men)

$89.97Current Price $89.97
(25% off)25% off.
$120.00Comparable value $120.00
Torhill Lo Chukka Boot (Men)
Clarks®

Torhill Lo Chukka Boot (Men)

$69.97Current Price $69.97
(46% off)46% off.
$130.00Comparable value $130.00
Only a few left
Moab 3 Waterproof Mid Hiking Boot (Men)
Merrell

Moab 3 Waterproof Mid Hiking Boot (Men)

$119.97Current Price $119.97
(40% off)40% off.
$200.00Comparable value $200.00
(47)
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