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Comfortable Shoes for Men

  • All Comfort
  • Boots
  • Dress Shoes
  • Loafers & Oxfords
  • Sneakers
1150 items
Grand Crosscourt Daily Sneaker (Men)
Top Deal
Cole Haan

Grand Crosscourt Daily Sneaker (Men)

$74.96 – $99.97Current Price $74.96 to $99.97
(Up to 64% off select items)Up to 64% off select items.
$210.00Comparable value $210.00
New Markdown
(177)
Grand Crosscourt LTT Slip-On Sneaker (Men)
Cole Haan

Grand Crosscourt LTT Slip-On Sneaker (Men)

$109.97Current Price $109.97
(42% off)42% off.
$190.00Comparable value $190.00
(20)
Grand Crosscourt Daily Laser Sneaker (Men)
Cole Haan

Grand Crosscourt Daily Laser Sneaker (Men)

$99.97Current Price $99.97
(48% off)48% off.
$195.00Comparable value $195.00
(43)
Sync Flex Derby (Men)
Dr. Scholl's

Sync Flex Derby (Men)

$59.97Current Price $59.97
(40% off)40% off.
$100.00Comparable value $100.00
(26)
Classic Low Top Sneaker (Men)
Top Deal
ECCO

Classic Low Top Sneaker (Men)

$49.99 – $79.97Current Price $49.99 to $79.97
(Up to 58% off select items)Up to 58% off select items.
$120.00Comparable value $120.00
(30)
Brody Driving Penny Loafer (Men)
Nordstrom

Brody Driving Penny Loafer (Men)

$69.97Current Price $69.97
(22% off)22% off.
$89.95Comparable value $89.95
(141)
Overtime Laser Sneaker - Wide Width Available (Men)
New
Dockers®

Overtime Laser Sneaker - Wide Width Available (Men)

$34.97Current Price $34.97
(41% off)41% off.
$60.00Comparable value $60.00
Torford Easy Loafer (Men)
New
Clarks®

Torford Easy Loafer (Men)

$69.97Current Price $69.97
(Up to 36% off)Up to 36% off.
$100.00 – $110.00Comparable value $100.00 to $110.00
GRANDPRO All Day Runner Sneaker (Men)
New
Cole Haan

GRANDPRO All Day Runner Sneaker (Men)

$99.97Current Price $99.97
(40% off)40% off.
$168.00Comparable value $168.00
Solevana Style Sneaker (Men)
Clarks®

Solevana Style Sneaker (Men)

$74.97Current Price $74.97
(25% off)25% off.
$100.00Comparable value $100.00
McGuffey 2 Plain Toe Knit Derby (Men)
Johnston & Murphy

McGuffey 2 Plain Toe Knit Derby (Men)

$49.97Current Price $49.97
(64% off)64% off.
$139.00Comparable value $139.00
(5)
Grand Remix Derby (Men)
Cole Haan

Grand Remix Derby (Men)

$99.97Current Price $99.97
(51% off)51% off.
$208.00Comparable value $208.00
(177)
Travel Slip-On (Men)
New
ECCO

Travel Slip-On (Men)

$79.97Current Price $79.97
(33% off)33% off.
$120.00Comparable value $120.00
Grand Atlantic Sneaker - Wide Width Available (Men)
Cole Haan

Grand Atlantic Sneaker - Wide Width Available (Men)

$89.97Current Price $89.97
(52% off)52% off.
$190.00Comparable value $190.00
(204)
GrandPro Rally LTT Sneaker (Men)
New
Cole Haan

GrandPro Rally LTT Sneaker (Men)

$109.97Current Price $109.97
(34% off)34% off.
$168.00Comparable value $168.00
Laeahi Kapa Slip-On (Men)
OluKai

Laeahi Kapa Slip-On (Men)

$59.97Current Price $59.97
(50% off)50% off.
$120.00Comparable value $120.00
(19)
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
(18)
Courtlite 2 Run Sneaker (Men)
New
Clarks®

Courtlite 2 Run Sneaker (Men)

$59.97Current Price $59.97
(45% off)45% off.
$110.00Comparable value $110.00
Grand+ Pureshot Court Sneaker (Men)
New
Cole Haan

Grand+ Pureshot Court Sneaker (Men)

$79.97Current Price $79.97
(Up to 36% off)Up to 36% off.
$120.00 – $125.00Comparable value $120.00 to $125.00
Motion Trek Sneaker (Men)
Clarks®

Motion Trek Sneaker (Men)

$69.97Current Price $69.97
(30% off)30% off.
$100.00Comparable value $100.00
(2)
Travel Penny Loafer (Men)
New
ECCO

Travel Penny Loafer (Men)

$79.97Current Price $79.97
(33% off)33% off.
$120.00Comparable value $120.00
Jaimie Derby Sneaker (Men)
Rockport

Jaimie Derby Sneaker (Men)

$89.95Current Price $89.95
(30% off)30% off.
$130.00Comparable value $130.00
Grand Crosscourt Traveler Sneaker (Men)
Cole Haan

Grand Crosscourt Traveler Sneaker (Men)

$49.48 – $109.97Current Price $49.48 to $109.97
(Up to 75% off select items)Up to 75% off select items.
$200.00Comparable value $200.00
(197)
Grand Crosscourt Daily Stitchlite Sneaker (Men)
Cole Haan

Grand Crosscourt Daily Stitchlite Sneaker (Men)

$67.47Current Price $67.47
(66% off)66% off.
$200.00Comparable value $200.00
(30)
Essentials Arizona Waterproof Slide Sandal (Men)
New
Birkenstock

Essentials Arizona Waterproof Slide Sandal (Men)

$29.96 – $49.95Current Price $29.96 to $49.95
(Up to 40% off select items)Up to 40% off select items.
$49.95Previous Price $49.95
(759)
Grand Crosscourt Winner Sneaker (Men)
Cole Haan

Grand Crosscourt Winner Sneaker (Men)

$69.96 – $99.97Current Price $69.96 to $99.97
(Up to 56% off select items)Up to 56% off select items.
$160.00 – $165.00Comparable value $160.00 to $165.00
New Markdown
(92)
Grand Leadshot Sneaker (Men)
Cole Haan

Grand Leadshot Sneaker (Men)

$79.97Current Price $79.97
(45% off)45% off.
$148.00Comparable value $148.00
(1)
Marcel Loafer (Men)
New
Børn

Marcel Loafer (Men)

$59.97Current Price $59.97
(45% off)45% off.
$110.00Comparable value $110.00
(1)
Flexway Step Slip-On (Men)
Clarks®

Flexway Step Slip-On (Men)

$74.97Current Price $74.97
(25% off)25% off.
$100.00Comparable value $100.00
(1)
Nantucket Penny Loafer Sneaker (Men)
New
Cole Haan

Nantucket Penny Loafer Sneaker (Men)

$89.97Current Price $89.97
(30% off)30% off.
$130.00Comparable value $130.00
Axton Slip-On (Men)
Nordstrom

Axton Slip-On (Men)

$69.97Current Price $69.97
(22% off)22% off.
$89.95Comparable value $89.95
(10)
Grand Shadowlite Stitchlite Derby (Men)
Cole Haan

Grand Shadowlite Stitchlite Derby (Men)

$99.97 – $109.97Current Price $99.97 to $109.97
(Up to 41% off)Up to 41% off.
$170.00Comparable value $170.00
Grand Crosscourt Sideserve Sneaker (Men)
New
Cole Haan

Grand Crosscourt Sideserve Sneaker (Men)

$79.97Current Price $79.97
(Up to 42% off)Up to 42% off.
$135.00 – $140.00Comparable value $135.00 to $140.00
(5)
Grand Rally Court Sneaker - Wide Width Available (Men)
Cole Haan

Grand Rally Court Sneaker - Wide Width Available (Men)

$69.97Current Price $69.97
(50% off)50% off.
$140.00Comparable value $140.00
(160)
CraftRally Ace Sneaker (Men)
New
Clarks®

CraftRally Ace Sneaker (Men)

$69.97Current Price $69.97
(41% off)41% off.
$120.00Comparable value $120.00
Neilson Sneaker (Men)
New
Dockers®

Neilson Sneaker (Men)

$59.97Current Price $59.97
(33% off)33% off.
$90.00Comparable value $90.00
Hyde II Moc Toe Loafer - Wide Width Available (Men)
NUNN BUSH

Hyde II Moc Toe Loafer - Wide Width Available (Men)

$49.97Current Price $49.97
(41% off)41% off.
$85.00Comparable value $85.00
(37)
Gravelle Low Moc Toe Derby (Men)
New
Clarks®

Gravelle Low Moc Toe Derby (Men)

$79.97Current Price $79.97
(42% off)42% off.
$140.00Comparable value $140.00
Flexway Step Slip-On (Men)
Clarks®

Flexway Step Slip-On (Men)

$59.97 – $74.97Current Price $59.97 to $74.97
(Up to 40% off)Up to 40% off.
$100.00Comparable value $100.00
Arizona Slide Sandal (Men)
Top Deal
Birkenstock

Arizona Slide Sandal (Men)

$117.95Current Price $117.95
(300)
Soft Classic Sneaker (Men)
ECCO

Soft Classic Sneaker (Men)

$55.96 – $64.98Current Price $55.96 to $64.98
(Up to 56% off)Up to 56% off.
$130.00Comparable value $130.00
(62)
Maddox Sneaker
Børn

Maddox Sneaker

$63.72 – $84.97Current Price $63.72 to $84.97
(Up to 46% off select items)Up to 46% off select items.
$120.00Comparable value $120.00
(14)
Banks Slip-On Sneaker (Men)
Børn

Banks Slip-On Sneaker (Men)

$59.97Current Price $59.97
(52% off)52% off.
$125.00Comparable value $125.00
(1)
Only a few left
Grand Crosscourt Premier Sneaker - Wide Width Available (Men)
Cole Haan

Grand Crosscourt Premier Sneaker - Wide Width Available (Men)

$49.48 – $109.97Current Price $49.48 to $109.97
(Up to 75% off select items)Up to 75% off select items.
$200.00Comparable value $200.00
(121)
T500 Tennis Sneaker (Men)
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
(124)
Original Grand Shortwing Oxford (Men)
Cole Haan

Original Grand Shortwing Oxford (Men)

$55.96 – $79.97Current Price $55.96 to $79.97
(Up to 65% off select items)Up to 65% off select items.
$160.00Comparable value $160.00
New Markdown
(298)
Baya Slide Sandal (Men)
CROCS

Baya Slide Sandal (Men)

Add to Bag or Wish List to see price(1787)
Kākaha Mesh Convertible Loafer (Men)
New
OluKai

Kākaha Mesh Convertible Loafer (Men)

$64.97Current Price $64.97
(35% off)35% off.
$100.00Comparable value $100.00
(28)
Speed Strike Hiking Shoe (Men)
New
Merrell

Speed Strike Hiking Shoe (Men)

$69.97Current Price $69.97
(22% off)22% off.
$90.00Comparable value $90.00
(9)
Marcman Wool Blend Lining Slipper (Men)
UGG®

Marcman Wool Blend Lining Slipper (Men)

$59.98 – $89.97Current Price $59.98 to $89.97
(Up to 50% off select items)Up to 50% off select items.
$120.00Comparable value $120.00
New Markdown
(82)
Nantucket Cross Strap Sandal (Men)
Cole Haan

Nantucket Cross Strap Sandal (Men)

$79.97Current Price $79.97
(42% off)42% off.
$140.00Comparable value $140.00
(13)
Cleve 07 Low Top Sneaker (Men)
Josef Seibel

Cleve 07 Low Top Sneaker (Men)

$64.97Current Price $64.97
(61% off)61% off.
$170.00Comparable value $170.00
(2)
Hodges Knit Derby (Men)
Johnston & Murphy

Hodges Knit Derby (Men)

$59.97Current Price $59.97
(64% off)64% off.
$169.00Comparable value $169.00
Grand Hurrion Stitchlite Wing Oxford (Men)
Cole Haan

Grand Hurrion Stitchlite Wing Oxford (Men)

$99.97Current Price $99.97
(50% off)50% off.
$200.00Comparable value $200.00
(78)
Ulele Flip Flop (Men)
OluKai

Ulele Flip Flop (Men)

$59.97Current Price $59.97
(33% off)33% off.
$90.00Comparable value $90.00
(106)
Chalet Chelsea Boot (Men)
Florsheim

Chalet Chelsea Boot (Men)

$69.96Current Price $69.96
(51% off)51% off.
$145.00Comparable value $145.00
New Markdown
(121)
OOahh Sport Slide Sandal (Men)
New
Oofos

OOahh Sport Slide Sandal (Men)

$34.97Current Price $34.97
(41% off)41% off.
$59.95Comparable value $59.95
Upton Knit Wingtip (Men)
Johnston & Murphy

Upton Knit Wingtip (Men)

$69.97Current Price $69.97
(55% off)55% off.
$159.00Comparable value $159.00
(24)
Grand Remix Derby Sneaker (Men)
Cole Haan

Grand Remix Derby Sneaker (Men)

$99.97Current Price $99.97
(41% off)41% off.
$170.00Comparable value $170.00
(66)
Braydon Knit Plain Toe Derby (Men)
Johnston & Murphy

Braydon Knit Plain Toe Derby (Men)

$59.97Current Price $59.97
(56% off)56% off.
$139.00Comparable value $139.00
(20)
Amherst 2.0 U-Throat Leather Sneaker (Men)
Johnston & Murphy

Amherst 2.0 U-Throat Leather Sneaker (Men)

$69.97Current Price $69.97
(49% off)49% off.
$139.00Comparable value $139.00
(128)
Classic Moc II Driving Shoe (Men)
ECCO

Classic Moc II Driving Shoe (Men)

$89.97Current Price $89.97
(35% off)35% off.
$140.00Comparable value $140.00
(112)
Solevana Style Sneaker (Men)
Clarks®

Solevana Style Sneaker (Men)

$74.97Current Price $74.97
(25% off)25% off.
$100.00Comparable value $100.00
Bend Venetian Driving Shoe (Men)
Nordstrom

Bend Venetian Driving Shoe (Men)

$69.97Current Price $69.97
(22% off)22% off.
$89.95Comparable value $89.95
(58)
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
(106)
Regent Loafer (Men)
New
Rockport

Regent Loafer (Men)

$49.97Current Price $49.97
(58% off)58% off.
$120.00Comparable value $120.00
Sailview Step Slip-On (Men)
Clarks®

Sailview Step Slip-On (Men)

$84.97Current Price $84.97
(22% off)22% off.
$110.00Comparable value $110.00
(1)
Kakaha Slip-On (Men)
OluKai

Kakaha Slip-On (Men)

$69.97Current Price $69.97
(46% off)46% off.
$130.00Comparable value $130.00
(59)
Aden Sneaker (Men)
Børn

Aden Sneaker (Men)

$21.24 – $84.97Current Price $21.24 to $84.97
(Up to 83% off select items)Up to 83% off select items.
$125.00Comparable value $125.00
New Markdown
(38)
GrandPro Breakaway Leather Sneaker (Men)
Cole Haan

GrandPro Breakaway Leather Sneaker (Men)

$74.96 – $99.97Current Price $74.96 to $99.97
(Up to 42% off select items)Up to 42% off select items.
$130.00 – $140.00Comparable value $130.00 to $140.00
New Markdown
(119)
Beck Tie Low Top Sneaker (Men)
Børn

Beck Tie Low Top Sneaker (Men)

$39.98 – $61.97Current Price $39.98 to $61.97
(Up to 68% off select items)Up to 68% off select items.
$120.00 – $125.00Comparable value $120.00 to $125.00
New Markdown
(8)
Flexway Band Slip-On (Men)
Clarks®

Flexway Band Slip-On (Men)

$59.97Current Price $59.97
(33% off)33% off.
$90.00Comparable value $90.00
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