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Comfortable Shoes for Men

  • All Comfort
  • Boots
  • Dress Shoes
  • Loafers & Oxfords
  • Sneakers
1202 items
550 Low Top Sneaker (Men)
New!
New Balance

550 Low Top Sneaker (Men)

$69.97Current Price $69.97
(41% off)41% off.
$119.99Comparable value $119.99
(15)
DOCKERS Garfield Cap Toe Dress Derby (Men)
Dockers®

DOCKERS Garfield Cap Toe Dress Derby (Men)

$59.99Current Price $59.99
(29% off)29% off.
$85.00Comparable value $85.00
(27)
GO RUN Razor 5 Running Shoe (Men)
SKECHERS

GO RUN Razor 5 Running Shoe (Men)

$84.97Current Price $84.97
(34% off)34% off.
$130.00Comparable value $130.00
(15)
Neumel High Weather Hybrid Waterproof Boot (Men)
UGG®

Neumel High Weather Hybrid Waterproof Boot (Men)

$99.97Current Price $99.97
(52% off)52% off.
$210.00Comparable value $210.00
(7)
Max Cushioning Endeavour Running Shoe (Men)
SKECHERS

Max Cushioning Endeavour Running Shoe (Men)

$49.97Current Price $49.97
(44% off)44% off.
$90.00Comparable value $90.00
(10)
Scottsdale Cap Toe Leather Derby - Wide Width Available (Men)
Florsheim

Scottsdale Cap Toe Leather Derby - Wide Width Available (Men)

$89.97Current Price $89.97
(30% off)30% off.
$130.00Comparable value $130.00
(16)
Neumel Shaggy Suede Chukka Boot (Men)
UGG®

Neumel Shaggy Suede Chukka Boot (Men)

$94.97Current Price $94.97
(36% off)36% off.
$150.00Comparable value $150.00
(2)
Newmarket Mid Lace Up Boot (Men)
New Markdown
Timberland

Newmarket Mid Lace Up Boot (Men)

$59.96Current Price $59.96
(60% off)60% off.
$150.00Comparable value $150.00
(4)
Steadwell Derby (Men)
Clarks®

Steadwell Derby (Men)

$59.97 – $79.97Current Price $59.97 to $79.97
(Up to 42% off)Up to 42% off.
$105.00Comparable value $105.00
Venture Daze Ultra Mini Genuine Shearling Platform Bootie (Women)
UGG®

Venture Daze Ultra Mini Genuine Shearling Platform Bootie (Women)

$134.97Current Price $134.97
(28% off)28% off.
$190.00Comparable value $190.00
(5)
Osborn Plain Toe Derby (Men)
Cole Haan

Osborn Plain Toe Derby (Men)

$65.98Current Price $65.98
(64% off)64% off.
$186.00Comparable value $186.00
(11)
Only a few left
Cory Embossed Penny Loafer (Men)
Rockport

Cory Embossed Penny Loafer (Men)

$99.95Current Price $99.95
(23% off)23% off.
$130.00Comparable value $130.00
(2)
Gender Inclusive 574 Sneaker
New Balance

Gender Inclusive 574 Sneaker

$38.98 – $59.97Current Price $38.98 to $59.97
(Up to 61% off select items)Up to 61% off select items.
$99.99Comparable value $99.99
(230)
Pregamo Moc Toe Bit Loafer (Men)
Florsheim

Pregamo Moc Toe Bit Loafer (Men)

$89.97Current Price $89.97
(37% off)37% off.
$145.00Comparable value $145.00
(45)
Jarvis Plain Toe Oxford (Men)
NUNN BUSH

Jarvis Plain Toe Oxford (Men)

$49.97Current Price $49.97
(44% off)44% off.
$90.00Comparable value $90.00
GO RUN Max Ride 11 Running Shoe (Men)
SKECHERS

GO RUN Max Ride 11 Running Shoe (Men)

$69.97Current Price $69.97
(47% off)47% off.
$133.00Comparable value $133.00
(30)
550 Basketball Sneaker (Men)
New Balance

550 Basketball Sneaker (Men)

$64.97Current Price $64.97
(50% off)50% off.
$130.00Comparable value $130.00
Only a few left
Newmark Grand Cap Toe Oxford (Men)
Cole Haan

Newmark Grand Cap Toe Oxford (Men)

$119.97Current Price $119.97
(61% off)61% off.
$308.00Comparable value $308.00
Carmelo Cap Toe Derby - Wide Width Available (Men)
NUNN BUSH

Carmelo Cap Toe Derby - Wide Width Available (Men)

$49.97Current Price $49.97
(44% off)44% off.
$90.00Comparable value $90.00
(9)
Dino Penny Loafer (Men)
Nordstrom

Dino Penny Loafer (Men)

$49.99 – $69.97Current Price $49.99 to $69.97
(Up to 49% off select items)Up to 49% off select items.
$99.95Comparable value $99.95
(80)
2.ZeroGrand Plain Toe Derby (Men)
Cole Haan

2.ZeroGrand Plain Toe Derby (Men)

$119.97Current Price $119.97
(58% off)58% off.
$289.00Comparable value $289.00
(45)
Only a few left
Newmark Grand Penny Loafer (Men)
Cole Haan

Newmark Grand Penny Loafer (Men)

$119.97Current Price $119.97
(61% off)61% off.
$308.00Comparable value $308.00
(2)
Arnolds Sneaker (Men)
ara

Arnolds Sneaker (Men)

$89.97Current Price $89.97
(52% off)52% off.
$190.00Comparable value $190.00
Only a few left
Garfield Plain Toe Chukka Boot (Men)
Deer Stags

Garfield Plain Toe Chukka Boot (Men)

$64.97Current Price $64.97
(35% off)35% off.
$100.00Comparable value $100.00
Sienna Derby (Men)
Deer Stags

Sienna Derby (Men)

$59.97Current Price $59.97
(33% off)33% off.
$90.00Comparable value $90.00
880 Fresh Foam Running Shoe (Men)
New!
New Balance

880 Fresh Foam Running Shoe (Men)

$59.97Current Price $59.97
(57% off)57% off.
$139.99Comparable value $139.99
(337)
Hydro Next Gen Hiking Sneaker (Men)
Merrell

Hydro Next Gen Hiking Sneaker (Men)

$54.97Current Price $54.97
(37% off)37% off.
$88.00Comparable value $88.00
(3)
Only a few left
Noah Penny Loafer (Men)
NUNN BUSH

Noah Penny Loafer (Men)

$89.97Current Price $89.97
(10% off)10% off.
$100.00Comparable value $100.00
480 Basketball Sneaker (Men)
New Balance

480 Basketball Sneaker (Men)

$59.97Current Price $59.97
(33% off)33% off.
$89.99Comparable value $89.99
(6)
Hudson Western Boot (Men)
Ariat

Hudson Western Boot (Men)

$149.97Current Price $149.97
(40% off)40% off.
$249.95Comparable value $249.95
(4)
Only a few left
Tynnar Sneaker (Men)
Rockport

Tynnar Sneaker (Men)

$59.97Current Price $59.97
(50% off)50% off.
$120.00Comparable value $120.00
(3)
Only a few left
Zionic Waterproof Hiking Boot (Men)
KEEN

Zionic Waterproof Hiking Boot (Men)

$94.97Current Price $94.97
(44% off)44% off.
$170.00Comparable value $170.00
(2)
Only a few left
MX 857 v3 Training Shoe (Men)
New!
New Balance

MX 857 v3 Training Shoe (Men)

$59.97Current Price $59.97
(57% off)57% off.
$139.99Comparable value $139.99
(156)
Only a few left
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
Harmon Grand Bit Loafer (Men)
Cole Haan

Harmon Grand Bit Loafer (Men)

$119.97Current Price $119.97
(61% off)61% off.
$310.00Comparable value $310.00
808 Skate Sneaker (Men)
New Balance

808 Skate Sneaker (Men)

$49.97Current Price $49.97
(58% off)58% off.
$120.00Comparable value $120.00
(10)
Sorrello Cap Toe Balmoral Oxford (Men)
Florsheim

Sorrello Cap Toe Balmoral Oxford (Men)

$99.97Current Price $99.97
(31% off)31% off.
$145.00Comparable value $145.00
(38)
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)
Gender Inclusive 740 Sneaker
New Balance

Gender Inclusive 740 Sneaker

$69.97Current Price $69.97
(36% off)36% off.
$109.99Comparable value $109.99
(7)
Go Run Swirl Tech Speed Sneaker (Men)
SKECHERS

Go Run Swirl Tech Speed Sneaker (Men)

$49.97Current Price $49.97
(54% off)54% off.
$110.00Comparable value $110.00
(4)
Shasta Gore-Tex® Waterproof Boot (Women)
New Markdown
UGG®

Shasta Gore-Tex® Waterproof Boot (Women)

$187.47Current Price $187.47
(62% off)62% off.
$500.00Comparable value $500.00
(12)
Max Cushioning Suspension Sneaker (Men)
SKECHERS

Max Cushioning Suspension Sneaker (Men)

$59.97Current Price $59.97
(42% off)42% off.
$105.00Comparable value $105.00
(14)
550 Basketball Sneaker (Men)
New Balance

550 Basketball Sneaker (Men)

$69.97Current Price $69.97
(36% off)36% off.
$109.99Comparable value $109.99
(8)
Sorrello Cap Toe Oxford (Men)
Florsheim

Sorrello Cap Toe Oxford (Men)

$89.97Current Price $89.97
(30% off)30% off.
$130.00Comparable value $130.00
(20)
Calderone Cap Toe Derby - Wide Width Available (Men)
NUNN BUSH

Calderone Cap Toe Derby - Wide Width Available (Men)

$54.97Current Price $54.97
(45% off)45% off.
$100.00Comparable value $100.00
(5)
Baltic Moc Toe Loafer (Men)
Dockers®

Baltic Moc Toe Loafer (Men)

$59.97Current Price $59.97
(29% off)29% off.
$85.00Comparable value $85.00
Only a few left
Futurity Time Western Boot (Men)
Ariat

Futurity Time Western Boot (Men)

$149.97Current Price $149.97
(46% off)46% off.
$279.95Comparable value $279.95
(68)
Only a few left
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
Townsend Chelsea Boot (Men)
Dockers®

Townsend Chelsea Boot (Men)

$39.97Current Price $39.97
(57% off)57% off.
$95.00Comparable value $95.00
(1)
Moab 3 Hiking Shoe (Men)
Merrell

Moab 3 Hiking Shoe (Men)

$59.97Current Price $59.97
(45% off)45% off.
$110.00Comparable value $110.00
(97)
Only a few left
Norcross Cap Toe Oxford (Men)
NUNN BUSH

Norcross Cap Toe Oxford (Men)

$89.97Current Price $89.97
(Up to 28% off)Up to 28% off.
$100.00 – $125.00Comparable value $100.00 to $125.00
Kore EZ Hero Plain Toe Monk Shoe (Men)
NUNN BUSH

Kore EZ Hero Plain Toe Monk Shoe (Men)

$69.97Current Price $69.97
(26% off)26% off.
$95.00Comparable value $95.00
Jarvis Cap Toe Oxford (Men)
NUNN BUSH

Jarvis Cap Toe Oxford (Men)

$49.97Current Price $49.97
(44% off)44% off.
$90.00Comparable value $90.00
Chicago Leather Oxford (Men)
Florsheim

Chicago Leather Oxford (Men)

$79.97Current Price $79.97
(36% off)36% off.
$125.00Comparable value $125.00
(136)
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)
Tasman Slipper (Men)
New!
UGG®

Tasman Slipper (Men)

$79.97Current Price $79.97
(27% off)27% off.
$110.00Comparable value $110.00
(517)
Santucci Cap Toe Derby (Men)
Florsheim

Santucci Cap Toe Derby (Men)

$79.97Current Price $79.97
(30% off)30% off.
$115.00Comparable value $115.00
(2)
Centro Formal Flex Cap Toe Derby (Wide Width Available) (Men)
NUNN BUSH

Centro Formal Flex Cap Toe Derby (Wide Width Available) (Men)

$54.97Current Price $54.97
(31% off)31% off.
$80.00Comparable value $80.00
Tatacoa Slingback Sport Sandal (Men)
Birkenstock

Tatacoa Slingback Sport Sandal (Men)

$74.97Current Price $74.97
(50% off)50% off.
$149.95Comparable value $149.95
(3)
Steadwell Dress Boot (Men)
Clarks®

Steadwell Dress Boot (Men)

$99.97Current Price $99.97
(23% off)23% off.
$130.00Comparable value $130.00
Ruvo Monk Shoe (Men)
New Markdown
Florsheim

Ruvo Monk Shoe (Men)

$64.98Current Price $64.98
(55% off)55% off.
$145.00Comparable value $145.00
(2)
Cory Penny Loafer (Men)
Rockport

Cory Penny Loafer (Men)

$99.95Current Price $99.95
(23% off)23% off.
$130.00Comparable value $130.00
Valencia Oxford (Men)
Deer Stags

Valencia Oxford (Men)

$59.97Current Price $59.97
(33% off)33% off.
$90.00Comparable value $90.00
Hawthorn Cap Toe Derby (Men)
Johnston & Murphy

Hawthorn Cap Toe Derby (Men)

$59.97Current Price $59.97
(59% off)59% off.
$149.00Comparable value $149.00
(2)
550 Basketball Sneaker (Men)
New Balance

550 Basketball Sneaker (Men)

$49.97Current Price $49.97
(58% off)58% off.
$120.00Comparable value $120.00
(67)
Harmon Cap Toe Derby (Men)
Johnston & Murphy

Harmon Cap Toe Derby (Men)

$59.97Current Price $59.97
(60% off)60% off.
$150.00Comparable value $150.00
(13)
Only a few left
Cambridge Slide Sandal (Men)
Eastland

Cambridge Slide Sandal (Men)

$69.97Current Price $69.97
(12% off)12% off.
$80.00Comparable value $80.00
(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
(40)
Lewis Cap Toe Derby (Men)
Johnston & Murphy

Lewis Cap Toe Derby (Men)

$49.99Current Price $49.99
(61% off)61% off.
$129.00Comparable value $129.00
(35)
Only a few left
Hawthorne Cap Toe Oxford (Men)
Cole Haan

Hawthorne Cap Toe Oxford (Men)

$119.97Current Price $119.97
(49% off)49% off.
$238.00Comparable value $238.00
(35)
Ringer Western Boot (Men)
Ariat

Ringer Western Boot (Men)

$129.97Current Price $129.97
(50% off)50% off.
$259.95Comparable value $259.95
(30)
Only a few left
Saltwater Duck Toe Boot (Men)
Sperry

Saltwater Duck Toe Boot (Men)

$39.97Current Price $39.97
(69% off)69% off.
$130.00Comparable value $130.00
(1)
Only a few left
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