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Comfortable Shoes for Men

  • All Comfort
  • Boots
  • Dress Shoes
  • Loafers & Oxfords
  • Sneakers
1202 items
WK400 II Walking Sneaker (Men)
KEEN

WK400 II Walking Sneaker (Men)

$79.97Current Price $79.97
(52% off)52% off.
$170.00Comparable value $170.00
(13)
Relaxlite Moc Toe Chukka (Men)
Clarks®

Relaxlite Moc Toe Chukka (Men)

$69.97Current Price $69.97
(30% off)30% off.
$100.00Comparable value $100.00
Only a few left
Tempo EXP Hiking Shoe (Men)
Merrell

Tempo EXP Hiking Shoe (Men)

$62.97Current Price $62.97
(21% off)21% off.
$80.00Comparable value $80.00
(2)
Gates Plain Toe Derby - Wide Width Available (Men)
NUNN BUSH

Gates Plain Toe Derby - Wide Width Available (Men)

$54.97Current Price $54.97
(38% off)38% off.
$90.00Comparable value $90.00
(2)
Milano Bold Buckle Sandal (Men)
Birkenstock

Milano Bold Buckle Sandal (Men)

$54.98 – $149.97Current Price $54.98 to $149.97
(Up to 59% off select items)Up to 59% off select items.
$135.00 – $220.00Comparable value $135.00 to $220.00
(1)
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)
Nantucket Penny Loafer (Men)
Cole Haan

Nantucket Penny Loafer (Men)

$69.97 – $89.97Current Price $69.97 to $89.97
(Up to 53% off)Up to 53% off.
$150.00Comparable value $150.00
(24)
Landon Low Top Sneaker (Men)
Dockers®

Landon Low Top Sneaker (Men)

$34.97Current Price $34.97
(41% off)41% off.
$60.00Comparable value $60.00
Gold Mako 2-Eye Boat Shoe (Men)
Sperry

Gold Mako 2-Eye Boat Shoe (Men)

$89.97Current Price $89.97
(48% off)48% off.
$175.00Comparable value $175.00
Only a few left
480 Basketball Sneaker (Men)
New Balance

480 Basketball Sneaker (Men)

$54.97Current Price $54.97
(38% off)38% off.
$89.99Comparable value $89.99
(211)
Numeric 440 v2 Skate Shoe (Men)
New Balance

Numeric 440 v2 Skate Shoe (Men)

$44.97Current Price $44.97
(43% off)43% off.
$79.99Comparable value $79.99
(20)
Agility Peak 5 Trek Sneaker (Men)
Merrell

Agility Peak 5 Trek Sneaker (Men)

$89.97Current Price $89.97
(51% off)51% off.
$185.00Comparable value $185.00
(2)
Gender Inclusive 9060 Sneaker
New Balance

Gender Inclusive 9060 Sneaker

$79.97Current Price $79.97
(46% off)46% off.
$149.99Comparable value $149.99
(734)
Jenson Chelsea Boot (Men)
New Markdown
Johnston & Murphy

Jenson Chelsea Boot (Men)

$136.48Current Price $136.48
(58% off)58% off.
$328.00Comparable value $328.00
(3)
Tayo Embossed Loafer (Men)
Rockport

Tayo Embossed Loafer (Men)

$39.97Current Price $39.97
(68% off)68% off.
$125.00Comparable value $125.00
(2)
Emmett Plain Toe Derby (Men)
Clarks®

Emmett Plain Toe Derby (Men)

$79.97Current Price $79.97
(27% off)27% off.
$110.00Comparable value $110.00
(1)
Edwin Weatherproof Lace-Up Boot (Men)
Aquatalia

Edwin Weatherproof Lace-Up Boot (Men)

$239.97Current Price $239.97
(58% off)58% off.
$575.00Comparable value $575.00
Gender Neutral 471 Sneaker
New!
New Balance

Gender Neutral 471 Sneaker

$59.97Current Price $59.97
(Up to 45% off)Up to 45% off.
$99.99 – $109.99Comparable value $99.99 to $109.99
(91)
Vito Sneaker (Men)
Mephisto

Vito Sneaker (Men)

$234.97Current Price $234.97
(9% off)9% off.
$259.00Comparable value $259.00
(4)
Only a few left
Lisbon SUPRO Derby (Men)
Deer Stags

Lisbon SUPRO Derby (Men)

$54.97Current Price $54.97
(26% off)26% off.
$75.00Comparable value $75.00
Gender Inclusive WRPD Runner Sneaker
New Balance

Gender Inclusive WRPD Runner Sneaker

$94.97Current Price $94.97
(36% off)36% off.
$150.00Comparable value $150.00
(13)
Log Cabin Slipper (Men)
New Markdown
Staheekum

Log Cabin Slipper (Men)

$18.72Current Price $18.72
(50% off)50% off.
$38.00Comparable value $38.00
Only a few left
530 Running Shoe (Men)
New!
New Balance

530 Running Shoe (Men)

$59.97Current Price $59.97
(45% off)45% off.
$109.99Comparable value $109.99
(29)
Otis II Chelsea Boot (Men)
NUNN BUSH

Otis II Chelsea Boot (Men)

$89.97Current Price $89.97
(18% off)18% off.
$110.00Comparable value $110.00
(1)
Calderone Wingtip Derby - Wide Width Available (Men)
NUNN BUSH

Calderone Wingtip Derby - Wide Width Available (Men)

$54.97Current Price $54.97
(45% off)45% off.
$100.00Comparable value $100.00
(9)
BB80 Basketball Sneaker (Men)
New Balance

BB80 Basketball Sneaker (Men)

$49.97 – $59.97Current Price $49.97 to $59.97
(Up to 33% off)Up to 33% off.
$74.99Comparable value $74.99
(80)
Allagash Standard Derby Boot (Men)
New Markdown
Eastland

Allagash Standard Derby Boot (Men)

$54.98 – $69.96Current Price $54.98 to $69.96
(Up to 62% off)Up to 62% off.
$145.00Comparable value $145.00
Chadwick Cap Toe Boot (Men)
New Markdown
Johnston & Murphy

Chadwick Cap Toe Boot (Men)

$67.47Current Price $67.47
(65% off)65% off.
$198.00Comparable value $198.00
(2)
FlexGrand 360 Wingtip Derby (Men)
New Markdown
Cole Haan

FlexGrand 360 Wingtip Derby (Men)

$58.48 – $67.47Current Price $58.48 to $67.47
(Up to 70% off)Up to 70% off.
$180.00 – $230.00Comparable value $180.00 to $230.00
(3)
Queenstown Plain Toe Derby (Men)
ECCO

Queenstown Plain Toe Derby (Men)

$99.97Current Price $99.97
(28% off)28% off.
$140.00Comparable value $140.00
(1)
Classic Mini Atherson Boot (Men)
UGG®

Classic Mini Atherson Boot (Men)

$99.97Current Price $99.97
(47% off)47% off.
$190.00Comparable value $190.00
(7)
Walkmaster Plain Toe Derby - Wide Width Available (Men)
Deer Stags

Walkmaster Plain Toe Derby - Wide Width Available (Men)

$74.97Current Price $74.97
(28% off)28% off.
$105.00Comparable value $105.00
(3)
Tempo Sol Hiking Sneaker (Men)
Merrell

Tempo Sol Hiking Sneaker (Men)

$62.97Current Price $62.97
(21% off)21% off.
$80.00Comparable value $80.00
(5)
GO RUN Supersonic Max Running Shoe (Men)
SKECHERS

GO RUN Supersonic Max Running Shoe (Men)

$49.97Current Price $49.97
(44% off)44% off.
$90.00Comparable value $90.00
(18)
Solano Slide Sandal (Men)
UGG®

Solano Slide Sandal (Men)

$59.97Current Price $59.97
(50% off)50% off.
$120.00Comparable value $120.00
(4)
Only a few left
Chalet Leather Cap Toe Boot (Men)
Florsheim

Chalet Leather Cap Toe Boot (Men)

$109.97Current Price $109.97
(29% off)29% off.
$155.00Comparable value $155.00
(16)
GO RUN Slip-Ins: Max Cushioning Sneaker (Men)
New!
SKECHERS

GO RUN Slip-Ins: Max Cushioning Sneaker (Men)

$59.97Current Price $59.97
(54% off)54% off.
$133.00Comparable value $133.00
Heritage Western Boot (Men)
New Markdown
Ariat

Heritage Western Boot (Men)

$99.96Current Price $99.96
(47% off)47% off.
$189.95Comparable value $189.95
(348)
Whitley Loafer (Men)
Rockport

Whitley Loafer (Men)

$99.95Current Price $99.95
(9% off)9% off.
$110.00Comparable value $110.00
(1)
Striper II CVO Sneaker (Men)
New Markdown
Sperry

Striper II CVO Sneaker (Men)

$22.47 – $29.97Current Price $22.47 to $29.97
(Up to 65% off select items)Up to 65% off select items.
$65.00Comparable value $65.00
(3)
1906A Running Shoe (Men)
New!
New Balance

1906A Running Shoe (Men)

$89.97Current Price $89.97
(47% off)47% off.
$169.99Comparable value $169.99
(99)
Matteo Sneaker (Men)
Florsheim

Matteo Sneaker (Men)

$89.97Current Price $89.97
(25% off)25% off.
$120.00Comparable value $120.00
(3)
Arizona Soft Slide Sandal (Men)
Birkenstock

Arizona Soft Slide Sandal (Men)

$154.95Current Price $154.95
(309)
Otto Derby (Men)
NUNN BUSH

Otto Derby (Men)

$19.98 – $49.97Current Price $19.98 to $49.97
(Up to 76% off select items)Up to 76% off select items.
$85.00Comparable value $85.00
(10)
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
Magna Gore-Tex® Waterproof Sneaker (Men)
ara

Magna Gore-Tex® Waterproof Sneaker (Men)

$89.97Current Price $89.97
(51% off)51% off.
$185.00Comparable value $185.00
(1)
Only a few left
Mateo Low Top Sneaker (Men)
New Markdown
Florsheim

Mateo Low Top Sneaker (Men)

$67.47Current Price $67.47
(43% off)43% off.
$120.00Comparable value $120.00
Curbside Faux Fur Lined Slipper
New Markdown
Staheekum

Curbside Faux Fur Lined Slipper

$22.47Current Price $22.47
(59% off)59% off.
$55.00Comparable value $55.00
(38)
Gender Inclusive Baya Marbled Clog
CROCS

Gender Inclusive Baya Marbled Clog

$39.97Current Price $39.97
(27% off)27% off.
$54.99Comparable value $54.99
(93)
Henson XC4 Waterproof Chukka Boot (Men)
Johnston & Murphy

Henson XC4 Waterproof Chukka Boot (Men)

$99.97 – $109.97Current Price $99.97 to $109.97
(Up to 49% off)Up to 49% off.
$199.00Comparable value $199.00
(18)
Bayaband Slide Sandal (Men)
CROCS

Bayaband Slide Sandal (Men)

$19.97Current Price $19.97
(33% off)33% off.
$29.99Comparable value $29.99
(1781)
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)
Rio Bravo Closed Toe Fisherman Sandal - Wide Width Available (Men)
NUNN BUSH

Rio Bravo Closed Toe Fisherman Sandal - Wide Width Available (Men)

$10.00 – $44.97Current Price $10.00 to $44.97
(Up to 86% off select items)Up to 86% off select items.
$75.00Comparable value $75.00
(35)
Stance Wingtip Derby - Wide Width Available (Men)
NUNN BUSH

Stance Wingtip Derby - Wide Width Available (Men)

$64.97Current Price $64.97
(27% off)27% off.
$90.00Comparable value $90.00
(6)
Only a few left
430 Sneaker (Men)
New!
New Balance

430 Sneaker (Men)

$39.97Current Price $39.97
(50% off)50% off.
$79.99Comparable value $79.99
(1)
Generation ZeroGrand Sneaker (Men)
Cole Haan

Generation ZeroGrand Sneaker (Men)

$69.97 – $79.97Current Price $69.97 to $79.97
(Up to 54% off)Up to 54% off.
$150.00 – $155.00Comparable value $150.00 to $155.00
(25)
Fly Strike 2 Hiking Shoe (Men)
Merrell

Fly Strike 2 Hiking Shoe (Men)

$62.97Current Price $62.97
(21% off)21% off.
$80.00Comparable value $80.00
(1)
Fowler Sneaker (Men)
Dockers®

Fowler Sneaker (Men)

$59.97Current Price $59.97
(29% off)29% off.
$85.00Comparable value $85.00
(1)
Belmont Plain Toe Derby (Men)
Deer Stags

Belmont Plain Toe Derby (Men)

$59.97Current Price $59.97
(33% off)33% off.
$90.00Comparable value $90.00
Arch Comfort Swift Fit Sneaker (Men)
SKECHERS

Arch Comfort Swift Fit Sneaker (Men)

$59.97Current Price $59.97
(29% off)29% off.
$85.00Comparable value $85.00
(7)
Truman Chelsea Boot (Men)
Dockers®

Truman Chelsea Boot (Men)

$59.97Current Price $59.97
(36% off)36% off.
$95.00Comparable value $95.00
(1)
Grand Series Jensen Sneaker (Men)
Cole Haan

Grand Series Jensen Sneaker (Men)

$89.97Current Price $89.97
(46% off)46% off.
$168.00Comparable value $168.00
(1)
Only a few left
Glide-Step Swift Sneaker (Men)
SKECHERS

Glide-Step Swift Sneaker (Men)

$54.97Current Price $54.97
(15% off)15% off.
$65.00Comparable value $65.00
(3)
1000D Sneaker (Men)
New!
New Balance

1000D Sneaker (Men)

$89.97Current Price $89.97
(40% off)40% off.
$149.99Comparable value $149.99
Infinity SUPRO Penny Loafer (Men)
Deer Stags

Infinity SUPRO Penny Loafer (Men)

$44.97Current Price $44.97
(50% off)50% off.
$90.00Comparable value $90.00
Ultra Flex 3.0 Smooth Step Slip-On Sneaker (Men)
SKECHERS

Ultra Flex 3.0 Smooth Step Slip-On Sneaker (Men)

$37.47 – $49.97Current Price $37.47 to $49.97
(Up to 60% off select items)Up to 60% off select items.
$95.00Comparable value $95.00
(6)
Only a few left
Banner Moc Toe Dress Loafer (Men)
Dockers®

Banner Moc Toe Dress Loafer (Men)

$59.97Current Price $59.97
(25% off)25% off.
$80.00Comparable value $80.00
740 Running Shoe (Men)
New!
New Balance

740 Running Shoe (Men)

$79.97Current Price $79.97
(Up to 30% off)Up to 30% off.
$109.99 – $114.99Comparable value $109.99 to $114.99
(30)
Newmark Grand Chelsea Boot (Men)
New Markdown
Cole Haan

Newmark Grand Chelsea Boot (Men)

$97.47Current Price $97.47
(72% off)72% off.
$360.00Comparable value $360.00
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
Dylan Chelsea Boot (Men)
Dockers®

Dylan Chelsea Boot (Men)

$59.97Current Price $59.97
(36% off)36% off.
$95.00Comparable value $95.00
(1)
Cham Redux 1TRL Sneaker (Men)
Merrell

Cham Redux 1TRL Sneaker (Men)

$99.97Current Price $99.97
(45% off)45% off.
$185.00Comparable value $185.00
(5)
Only a few left
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