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Comfortable Shoes for Men

  • All Comfort
  • Boots
  • Dress Shoes
  • Loafers & Oxfords
  • Sneakers
1175 items
T500 Tennis Sneaker (Men)
Upgrade to get by Christmas
New Balance

T500 Tennis Sneaker (Men)

$49.97 – $69.97Current Price $49.97 to $69.97
(Up to 54% off)Up to 54% off.
$109.99Comparable value $109.99
(97)
Grand Crosscourt Daily Sneaker (Men)
Upgrade to get by Christmas
Cole Haan

Grand Crosscourt Daily Sneaker (Men)

$99.97Current Price $99.97
(52% off)52% off.
$210.00Comparable value $210.00
(153)
Grand Remix Derby (Men)
Upgrade to get by Christmas
Cole Haan

Grand Remix Derby (Men)

$69.96 – $109.97Current Price $69.96 to $109.97
(Up to 66% off select items)Up to 66% off select items.
$208.00Comparable value $208.00
(91)
Marcman Wool Blend Lining Slipper (Men)
Top Deal
UGG®

Marcman Wool Blend Lining Slipper (Men)

$89.97Current Price $89.97
(28% off)28% off.
$125.00Comparable value $125.00
(48)
Grand Crosscourt Winner Sneaker (Men)
Upgrade to get by Christmas
Cole Haan

Grand Crosscourt Winner Sneaker (Men)

$74.96 – $99.97Current Price $74.96 to $99.97
(Up to 53% off select items)Up to 53% off select items.
$160.00Comparable value $160.00
(72)
Grand Crosscourt Traveler Sneaker (Men)
New Markdown
Cole Haan

Grand Crosscourt Traveler Sneaker (Men)

$82.47 – $109.97Current Price $82.47 to $109.97
(Up to 58% off select items)Up to 58% off select items.
$200.00Comparable value $200.00
(191)
Grand Crosscourt Daily Laser Sneaker (Men)
Upgrade to get by Christmas
Cole Haan

Grand Crosscourt Daily Laser Sneaker (Men)

$99.97Current Price $99.97
(48% off)48% off.
$195.00Comparable value $195.00
(23)
Grand Crosscourt LTT Slip-On Sneaker (Men)
Upgrade to get by Christmas
Cole Haan

Grand Crosscourt LTT Slip-On Sneaker (Men)

$109.97Current Price $109.97
(42% off)42% off.
$190.00Comparable value $190.00
(9)
Arizona Slide Sandal (Men)
Upgrade to get by Christmas
Birkenstock

Arizona Slide Sandal (Men)

$84.99 – $117.95Current Price $84.99 to $117.95
(Up to 27% off select items)Up to 27% off select items.
$117.95Previous Price $117.95
(279)
Bedford Penny Loafer (Men)
Upgrade to get by Christmas
Cole Haan

Bedford Penny Loafer (Men)

$99.97Current Price $99.97
(67% off)67% off.
$306.00Comparable value $306.00
(50)
Classic Low Top Sneaker (Men)
Upgrade to get by Christmas
ECCO

Classic Low Top Sneaker (Men)

$53.98 – $79.97Current Price $53.98 to $79.97
(Up to 55% off select items)Up to 55% off select items.
$120.00Comparable value $120.00
(19)
Grand Remix Derby Sneaker (Men)
Upgrade to get by Christmas
Cole Haan

Grand Remix Derby Sneaker (Men)

$99.97Current Price $99.97
(41% off)41% off.
$170.00Comparable value $170.00
(43)
Surveyor 2-Eye Boat Shoe (Men)
New!
Sperry

Surveyor 2-Eye Boat Shoe (Men)

$64.97Current Price $64.97
(35% off)35% off.
$100.00Comparable value $100.00
Alder Faux Shearling Lined Suede Slipper (Men)
Top Deal
UGG®

Alder Faux Shearling Lined Suede Slipper (Men)

$79.97Current Price $79.97
(20% off)20% off.
$100.00Comparable value $100.00
(526)
Bedford Cap Toe Derby (Men)
Upgrade to get by Christmas
Cole Haan

Bedford Cap Toe Derby (Men)

$99.97Current Price $99.97
(Up to 67% off)Up to 67% off.
$298.00 – $306.00Comparable value $298.00 to $306.00
(73)
Chamberlin Grand Water Resistant Chelsea Boot (Men)
Cole Haan

Chamberlin Grand Water Resistant Chelsea Boot (Men)

$129.97Current Price $129.97
(50% off)50% off.
$260.00Comparable value $260.00
(4)
Aden Sneaker (Men)
New Markdown
Børn

Aden Sneaker (Men)

$46.73 – $84.97Current Price $46.73 to $84.97
(Up to 62% off select items)Up to 62% off select items.
$125.00Comparable value $125.00
(33)
Soft Classic Sneaker (Men)
New Markdown
ECCO

Soft Classic Sneaker (Men)

$44.98 – $99.97Current Price $44.98 to $99.97
(Up to 65% off select items)Up to 65% off select items.
$130.00Comparable value $130.00
(59)
Leisure Nomad Slipper (Men)
Top Deal
UGG®

Leisure Nomad Slipper (Men)

$89.97Current Price $89.97
(21% off)21% off.
$115.00Comparable value $115.00
(7)
515 Sneaker (Men)
New!
New Balance

515 Sneaker (Men)

Add to Bag or Wish List to see price(4)
272 Skate Sneaker (Men)
Upgrade to get by Christmas
New Balance

272 Skate Sneaker (Men)

$39.97Current Price $39.97
(50% off)50% off.
$79.99Comparable value $79.99
(10)
Grand Hurrion Stitchlite Wing Oxford (Men)
Cole Haan

Grand Hurrion Stitchlite Wing Oxford (Men)

$64.98 – $99.97Current Price $64.98 to $99.97
(Up to 67% off select items)Up to 67% off select items.
$200.00Comparable value $200.00
(59)
Grand Atlantic Derby (Men)
Cole Haan

Grand Atlantic Derby (Men)

$69.97 – $79.97Current Price $69.97 to $79.97
(Up to 68% off)Up to 68% off.
$220.00Comparable value $220.00
(101)
Gender Inclusive T500 Tennis Sneaker
New!
New Balance

Gender Inclusive T500 Tennis Sneaker

$69.97Current Price $69.97
(36% off)36% off.
$109.99Comparable value $109.99
(106)
Bedford Plain Toe Derby (Men)
Cole Haan

Bedford Plain Toe Derby (Men)

$59.97 – $99.97Current Price $59.97 to $99.97
(Up to 79% off)Up to 79% off.
$298.00 – $306.00Comparable value $298.00 to $306.00
(36)
Morse Grand 360 Plain Toe Derby (Men)
Upgrade to get by Christmas
Cole Haan

Morse Grand 360 Plain Toe Derby (Men)

$119.97Current Price $119.97
(40% off)40% off.
$200.00Comparable value $200.00
(7)
Grand Crosscourt Premier Sneaker - Wide Width Available (Men)
Cole Haan

Grand Crosscourt Premier Sneaker - Wide Width Available (Men)

$109.97Current Price $109.97
(45% off)45% off.
$200.00Comparable value $200.00
(76)
Chamberlin Grand Plain Toe Derby (Men)
Upgrade to get by Christmas
Cole Haan

Chamberlin Grand Plain Toe Derby (Men)

$109.97Current Price $109.97
(52% off)52% off.
$230.00Comparable value $230.00
(3)
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)
Leisure Nomad Slide Slipper (Men)
Top Deal
UGG®

Leisure Nomad Slide Slipper (Men)

$79.97Current Price $79.97
(23% off)23% off.
$105.00Comparable value $105.00
(10)
Grand Crosscourt II Sneaker - Wide Width Available (Men)
Cole Haan

Grand Crosscourt II Sneaker - Wide Width Available (Men)

$99.97Current Price $99.97
(Up to 44% off)Up to 44% off.
$170.00 – $180.00Comparable value $170.00 to $180.00
(394)
Grand Hurrion Cup LTT Low Top Sneaker (Men)
Cole Haan

Grand Hurrion Cup LTT Low Top Sneaker (Men)

$119.97Current Price $119.97
(42% off)42% off.
$210.00Comparable value $210.00
(1)
Crosslander 3 Hiking Shoe (Men)
Merrell

Crosslander 3 Hiking Shoe (Men)

Add to Bag or Wish List to see price(77)
Allegheny II Sneaker (Men)
Upgrade to get by Christmas
Børn

Allegheny II Sneaker (Men)

$59.97Current Price $59.97
(53% off)53% off.
$130.00Comparable value $130.00
(3)
Beck Tie Low Top Sneaker (Men)
Upgrade to get by Christmas
Børn

Beck Tie Low Top Sneaker (Men)

$59.97Current Price $59.97
(52% off)52% off.
$125.00Comparable value $125.00
515 Sneaker (Men)
Upgrade to get by Christmas
New Balance

515 Sneaker (Men)

Add to Bag or Wish List to see price(3)
Boston Clog (Men)
New Markdown
Birkenstock

Boston Clog (Men)

$35.96 – $59.95Current Price $35.96 to $59.95
(Up to 40% off select items)Up to 40% off select items.
$59.95Previous Price $59.95
(55)
Grand Crosscourt Daily Court Sneaker (Men)
Cole Haan

Grand Crosscourt Daily Court Sneaker (Men)

$109.97Current Price $109.97
(31% off)31% off.
$160.00Comparable value $160.00
(1)
Moab 3 Ready Zip Hiking Sneaker (Men)
Upgrade to get by Christmas
Merrell

Moab 3 Ready Zip Hiking Sneaker (Men)

$79.97Current Price $79.97
(42% off)42% off.
$140.00Comparable value $140.00
(10)
Grand Crosscourt Traveler Setshot Sneaker (Men)
Upgrade to get by Christmas
Cole Haan

Grand Crosscourt Traveler Setshot Sneaker (Men)

$65.98 – $109.97Current Price $65.98 to $109.97
(Up to 67% off select items)Up to 67% off select items.
$200.00Comparable value $200.00
Grand Crosscourt 20.4.7 Sneaker (Men)
Upgrade to get by Christmas
Cole Haan

Grand Crosscourt 20.4.7 Sneaker (Men)

$109.97Current Price $109.97
(37% off)37% off.
$175.00Comparable value $175.00
Gold Mako 2-Eye Boat Shoe (Men)
Upgrade to get by Christmas
Sperry

Gold Mako 2-Eye Boat Shoe (Men)

$89.97Current Price $89.97
(48% off)48% off.
$175.00Comparable value $175.00
997H Sneaker (Men)
New Balance

997H Sneaker (Men)

$72.97 – $79.97Current Price $72.97 to $79.97
(Up to 27% off)Up to 27% off.
$94.99 – $99.99Comparable value $94.99 to $99.99
(47)
Highpoint Plain Toe Derby (Men)
Florsheim

Highpoint Plain Toe Derby (Men)

$38.98 – $59.97Current Price $38.98 to $59.97
(Up to 64% off select items)Up to 64% off select items.
$110.00Comparable value $110.00
(30)
Kore City Walk EZ Sneaker (Men)
NUNN BUSH

Kore City Walk EZ Sneaker (Men)

$49.97Current Price $49.97
(41% off)41% off.
$85.00Comparable value $85.00
(6)
Numeric 440 v2 Skate Shoe (Men)
Upgrade to get by Christmas
New Balance

Numeric 440 v2 Skate Shoe (Men)

$44.97Current Price $44.97
(43% off)43% off.
$79.99Comparable value $79.99
(20)
Speed Strike 2 Hiking Shoe (Men)
Upgrade to get by Christmas
Merrell

Speed Strike 2 Hiking Shoe (Men)

$79.97Current Price $79.97
(20% off)20% off.
$100.00Comparable value $100.00
(1)
Zermatt 365 Clog (Men)
Birkenstock

Zermatt 365 Clog (Men)

$148.95Current Price $148.95
(10)
Grand Leadshot Sneaker (Men)
Cole Haan

Grand Leadshot Sneaker (Men)

$79.97Current Price $79.97
(45% off)45% off.
$148.00Comparable value $148.00
Craftwell Lace-Up Sneaker (Men)
Clarks®

Craftwell Lace-Up Sneaker (Men)

$69.97Current Price $69.97
(30% off)30% off.
$100.00Comparable value $100.00
Boswell Chukka Boot (Men)
Upgrade to get by Christmas
Johnston & Murphy

Boswell Chukka Boot (Men)

$89.97Current Price $89.97
(48% off)48% off.
$175.00Comparable value $175.00
(10)
Tayton Step Activated Sneaker (Men)
Upgrade to get by Christmas
Rockport

Tayton Step Activated Sneaker (Men)

$39.97Current Price $39.97
(66% off)66% off.
$120.00Comparable value $120.00
(1)
Craftwell Slip-On (Men)
Clarks®

Craftwell Slip-On (Men)

$69.97Current Price $69.97
(30% off)30% off.
$100.00Comparable value $100.00
(1)
Kyoto Desert Slide Sandal (Men)
New!
Birkenstock

Kyoto Desert Slide Sandal (Men)

$74.96 – $99.97Current Price $74.96 to $99.97
(Up to 51% off select items)Up to 51% off select items.
$155.00Comparable value $155.00
(9)
Arizona Vintage Bold Grip Sandal (Men)
Upgrade to get by Christmas
Birkenstock

Arizona Vintage Bold Grip Sandal (Men)

$89.97Current Price $89.97
(33% off)33% off.
$135.00Comparable value $135.00
Grand Hurrion Stitchlite™ Plain Toe Oxford (Men)
Cole Haan

Grand Hurrion Stitchlite™ Plain Toe Oxford (Men)

$99.97Current Price $99.97
(47% off)47% off.
$190.00Comparable value $190.00
(13)
Bradley Loafer (Men) (Wide Width Available)
Clarks®

Bradley Loafer (Men) (Wide Width Available)

$69.97Current Price $69.97
(26% off)26% off.
$95.00Comparable value $95.00
(8)
Essentials Arizona Waterproof Slide Sandal (Men)
Upgrade to get by Christmas
Birkenstock

Essentials Arizona Waterproof Slide Sandal (Men)

$11.98 – $49.95Current Price $11.98 to $49.95
(Up to 76% off select items)Up to 76% off select items.
$49.95Previous Price $49.95
(746)
Jace Sneaker (Men)
New Markdown
Nordstrom

Jace Sneaker (Men)

$34.98 – $59.97Current Price $34.98 to $59.97
(Up to 61% off select items)Up to 61% off select items.
$89.95Comparable value $89.95
(64)
Morse GRANDFØAM Chukka Boot (Men)
Cole Haan

Morse GRANDFØAM Chukka Boot (Men)

$129.97Current Price $129.97
(40% off)40% off.
$220.00Comparable value $220.00
Attleboro Chelsea Boot (Men)
Upgrade to get by Christmas
Timberland

Attleboro Chelsea Boot (Men)

$69.97Current Price $69.97
(Up to 50% off)Up to 50% off.
$130.00 – $140.00Comparable value $130.00 to $140.00
(6)
997H Sneaker (Men)
Upgrade to get by Christmas
New Balance

997H Sneaker (Men)

$49.97 – $79.97Current Price $49.97 to $79.97
(Up to 47% off)Up to 47% off.
$94.99 – $99.99Comparable value $94.99 to $99.99
(5)
2.ZeroGrand Laser Wing Derby (Men)
Upgrade to get by Christmas
Cole Haan

2.ZeroGrand Laser Wing Derby (Men)

$99.97Current Price $99.97
(Up to 67% off)Up to 67% off.
$300.00 – $308.00Comparable value $300.00 to $308.00
(1665)
American Classics Montrose Plain Toe Derby (Men)
Upgrade to get by Christmas
Cole Haan

American Classics Montrose Plain Toe Derby (Men)

$99.97Current Price $99.97
(50% off)50% off.
$200.00Comparable value $200.00
Twins Mismatched Sneakers (Men)
Camper

Twins Mismatched Sneakers (Men)

$104.97Current Price $104.97
(36% off)36% off.
$165.00Comparable value $165.00
(1)
Only a few left
Grandsport Journey Knit Sneaker (Men)
Cole Haan

Grandsport Journey Knit Sneaker (Men)

$49.99 – $79.97Current Price $49.99 to $79.97
(Up to 72% off select items)Up to 72% off select items.
$180.00Comparable value $180.00
(101)
Gender Inclusive Made in USA 996 V1 Sneaker
Upgrade to get by Christmas
New Balance

Gender Inclusive Made in USA 996 V1 Sneaker

$79.97Current Price $79.97
(54% off)54% off.
$174.99Comparable value $174.99
(93)
GrandPro Topspin Sneaker (Men)
Cole Haan

GrandPro Topspin Sneaker (Men)

$99.97Current Price $99.97
(40% off)40% off.
$168.00Comparable value $168.00
(330)
Numeric Brandon Westgate 508 Sneaker (Men)
Upgrade to get by Christmas
New Balance

Numeric Brandon Westgate 508 Sneaker (Men)

$34.96Current Price $34.96
(61% off)61% off.
$90.00Comparable value $90.00
(41)
Moab Speed 2 Waterproof Hiking Shoe (Men)
Upgrade to get by Christmas
Merrell

Moab Speed 2 Waterproof Hiking Shoe (Men)

$89.97Current Price $89.97
(47% off)47% off.
$170.00Comparable value $170.00
(16)
Jenson Low Top Sneaker (Men)
Dockers®

Jenson Low Top Sneaker (Men)

$34.97Current Price $34.97
(41% off)41% off.
$60.00Comparable value $60.00
Kore City Rally Low Top Sneaker (Men)
New!
NUNN BUSH

Kore City Rally Low Top Sneaker (Men)

$59.97Current Price $59.97
(29% off)29% off.
$85.00Comparable value $85.00
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