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Comfortable Shoes for Men

  • All Comfort
  • Boots
  • Dress Shoes
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  • Sneakers
1353 items
Keefer Loafer (Men)
New
Rockport

Keefer Loafer (Men)

$94.97Current Price $94.97
(29% off)29% off.
$135.00Comparable value $135.00
Generation ZeroGrand Stitchlite Sneaker (Men)
Cole Haan

Generation ZeroGrand Stitchlite Sneaker (Men)

$69.97Current Price $69.97
(54% off)54% off.
$155.00Comparable value $155.00
(506)
Donovan 04 Low Top Sneaker (Men)
New
Josef Seibel

Donovan 04 Low Top Sneaker (Men)

$69.97Current Price $69.97
(57% off)57% off.
$165.00Comparable value $165.00
Montauk Resort Flip Flop (Men)
New
Cole Haan

Montauk Resort Flip Flop (Men)

$59.97Current Price $59.97
(50% off)50% off.
$120.00Comparable value $120.00
(1)
Kore City Walk EZ Slip-On Sneaker (Men) (Wide Width Available)
NUNN BUSH

Kore City Walk EZ Slip-On Sneaker (Men) (Wide Width Available)

$39.97Current Price $39.97
(52% off)52% off.
$85.00Comparable value $85.00
(20)
Classic Crafted Faux Suede Clog (Men)
CROCS

Classic Crafted Faux Suede Clog (Men)

$39.97Current Price $39.97
(42% off)42% off.
$70.00Comparable value $70.00
Bedford Cap Toe Derby (Men)
Top Deal
Cole Haan

Bedford Cap Toe Derby (Men)

$79.97 – $99.97Current Price $79.97 to $99.97
(Up to 73% off)Up to 73% off.
$298.00 – $306.00Comparable value $298.00 to $306.00
(89)
Kore City Walk EZ Sneaker - Wide Width Available (Men)
NUNN BUSH

Kore City Walk EZ Sneaker - Wide Width Available (Men)

$49.97Current Price $49.97
(Up to 41% off)Up to 41% off.
$80.00 – $85.00Comparable value $80.00 to $85.00
(13)
Grand Crosscourt Tennis II Sneaker (Men)
Cole Haan

Grand Crosscourt Tennis II Sneaker (Men)

$109.97Current Price $109.97
(Up to 35% off)Up to 35% off.
$160.00 – $170.00Comparable value $160.00 to $170.00
(5)
Bend Chelsea Boot (Men)
Birkenstock

Bend Chelsea Boot (Men)

$64.98Current Price $64.98
(61% off)61% off.
$170.00Comparable value $170.00
(2)
Grand Shadowlite Wingtip Derby (Men)
Cole Haan

Grand Shadowlite Wingtip Derby (Men)

$99.97Current Price $99.97
(50% off)50% off.
$200.00Comparable value $200.00
(1)
Fairlead CVO Sneaker (Men)
Sperry

Fairlead CVO Sneaker (Men)

$34.97Current Price $34.97
(53% off)53% off.
$75.00Comparable value $75.00
(3)
Davenport Venetian Driving Loafer (Men)
New
Sperry

Davenport Venetian Driving Loafer (Men)

$59.97Current Price $59.97
(45% off)45% off.
$110.00Comparable value $110.00
Naples Bold Grip Clog (Men)
Birkenstock

Naples Bold Grip Clog (Men)

$119.97Current Price $119.97
(25% off)25% off.
$160.00Comparable value $160.00
(6)
Tyler 38 Slip-On (Men)
Josef Seibel

Tyler 38 Slip-On (Men)

$64.97Current Price $64.97
(56% off)56% off.
$150.00Comparable value $150.00
(4)
Newport H2 Water Hiking Sandal (Men)
New
KEEN

Newport H2 Water Hiking Sandal (Men)

$59.97Current Price $59.97
(53% off)53% off.
$130.00Comparable value $130.00
(4)
Dresslite Bike Toe Slip-On (Men)
New
Clarks®

Dresslite Bike Toe Slip-On (Men)

$74.97 – $79.97Current Price $74.97 to $79.97
(Up to 23% off)Up to 23% off.
$95.00 – $105.00Comparable value $95.00 to $105.00
Twins Mismatched Lace-Up Sneaker (Men)
Camper

Twins Mismatched Lace-Up Sneaker (Men)

$164.97Current Price $164.97
(41% off)41% off.
$280.00Comparable value $280.00
(1)
Guideview Fisherman Sandal (Men)
Clarks®

Guideview Fisherman Sandal (Men)

$74.97Current Price $74.97
(25% off)25% off.
$100.00Comparable value $100.00
Lagrange Moc Toe Loafer (Men)
ara

Lagrange Moc Toe Loafer (Men)

$79.97Current Price $79.97
(50% off)50% off.
$160.00Comparable value $160.00
Grand Plain Toe Derby (Men)
Cole Haan

Grand Plain Toe Derby (Men)

$79.97Current Price $79.97
(50% off)50% off.
$160.00Comparable value $160.00
(11)
Newmark Grand Penny Loafer (Men)
Cole Haan

Newmark Grand Penny Loafer (Men)

$79.98Current Price $79.98
(74% off)74% off.
$308.00Comparable value $308.00
(3)
Only a few left
Tyler 10 Penny Loafer (Men)
Josef Seibel

Tyler 10 Penny Loafer (Men)

$64.97Current Price $64.97
(56% off)56% off.
$150.00Comparable value $150.00
Slip-In® Skech-Air Element 2.0 Slip-On Sneaker (Men)
SKECHERS

Slip-In® Skech-Air Element 2.0 Slip-On Sneaker (Men)

$49.97Current Price $49.97
(50% off)50% off.
$100.00Comparable value $100.00
(25)
Ohana Flip Flop (Men)
New
OluKai

Ohana Flip Flop (Men)

$38.98 – $59.97Current Price $38.98 to $59.97
(Up to 51% off select items)Up to 51% off select items.
$80.00Comparable value $80.00
(317)
Griff Plain Toe Derby (Wide Width Available) (Men)
NUNN BUSH

Griff Plain Toe Derby (Wide Width Available) (Men)

$54.97Current Price $54.97
(Up to 38% off)Up to 38% off.
$85.00 – $90.00Comparable value $85.00 to $90.00
Hodges Plain Toe Oxford (Men)
New
Johnston & Murphy

Hodges Plain Toe Oxford (Men)

$79.97Current Price $79.97
(52% off)52% off.
$169.00Comparable value $169.00
Gessler Derby (Men)
Clarks®

Gessler Derby (Men)

$59.97Current Price $59.97
(36% off)36% off.
$95.00Comparable value $95.00
(4)
Steadwell Slip-On Derby (Men)
Clarks®

Steadwell Slip-On 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
Earl Plain Toe Derby (Men)
New
Josef Seibel

Earl Plain Toe Derby (Men)

$59.97Current Price $59.97
(64% off)64% off.
$170.00Comparable value $170.00
(1)
Mapstone Trail Sneaker (Men)
New
Clarks®

Mapstone Trail Sneaker (Men)

$69.97Current Price $69.97
(46% off)46% off.
$130.00Comparable value $130.00
Tyler 09 Derby (Men)
Josef Seibel

Tyler 09 Derby (Men)

$64.97Current Price $64.97
(56% off)56% off.
$150.00Comparable value $150.00
Twins Sneaker (Men)
Camper

Twins Sneaker (Men)

$179.97Current Price $179.97
(36% off)36% off.
$285.00Comparable value $285.00
(2)
Oslo Moc Toe Penny Loafer (Men)
NUNN BUSH

Oslo Moc Toe Penny Loafer (Men)

$54.97Current Price $54.97
(31% off)31% off.
$80.00Comparable value $80.00
Maddox Sneaker
Børn

Maddox Sneaker

$84.97Current Price $84.97
(29% off)29% off.
$120.00Comparable value $120.00
(14)
Bend Decon Sneaker (Men)
Birkenstock

Bend Decon Sneaker (Men)

$64.98Current Price $64.98
(59% off)59% off.
$160.00Comparable value $160.00
(5)
Weltridge Derby (Men)
Clarks®

Weltridge Derby (Men)

$74.97Current Price $74.97
(31% off)31% off.
$110.00Comparable value $110.00
2.ZeroGrand Stitchlite Water Resistant Wingtip (Men)
Cole Haan

2.ZeroGrand Stitchlite Water Resistant Wingtip (Men)

$109.97Current Price $109.97
(47% off)47% off.
$209.00Comparable value $209.00
(1214)
Gibbons Wingtip Derby (Men)
Johnston & Murphy

Gibbons Wingtip Derby (Men)

$69.97Current Price $69.97
(45% off)45% off.
$129.00Comparable value $129.00
(3)
574V Sneaker (Men)
New Balance

574V Sneaker (Men)

$34.96 – $37.47Current Price $34.96 to $37.47
(Up to 61% off)Up to 61% off.
$89.99Comparable value $89.99
(20)
Otto Plain Toe Derby - Wide Width Available (Men)
NUNN BUSH

Otto Plain Toe Derby - Wide Width Available (Men)

$54.97 – $74.97Current Price $54.97 to $74.97
(Up to 40% off)Up to 40% off.
$85.00 – $100.00Comparable value $85.00 to $100.00
(7)
Striper II Slip-On Sneaker (Men)
New
Sperry

Striper II Slip-On Sneaker (Men)

$34.97Current Price $34.97
(46% off)46% off.
$65.00Comparable value $65.00
Langley Penny Loafer (Men)
Børn

Langley Penny Loafer (Men)

$59.97 – $62.96Current Price $59.97 to $62.96
(Up to 57% off)Up to 57% off.
$140.00Comparable value $140.00
(10)
Motion Trek Sneaker (Men)
Clarks®

Motion Trek Sneaker (Men)

$69.97Current Price $69.97
(30% off)30% off.
$100.00Comparable value $100.00
(2)
Amherst GL1 Luxe Hybrid Waterproof Golf Sneaker (Men)
Johnston & Murphy

Amherst GL1 Luxe Hybrid Waterproof Golf Sneaker (Men)

$79.97Current Price $79.97
(46% off)46% off.
$149.00Comparable value $149.00
(20)
Grand Venetian Driver Loafer (Men)
Cole Haan

Grand Venetian Driver Loafer (Men)

$79.97Current Price $79.97
(42% off)42% off.
$140.00Comparable value $140.00
Chalet Chelsea Boot (Men)
Florsheim

Chalet Chelsea Boot (Men)

$69.96Current Price $69.96
(51% off)51% off.
$145.00Comparable value $145.00
(124)
Queenstown Penny Loafer (Men)
ECCO

Queenstown Penny Loafer (Men)

$99.97Current Price $99.97
(28% off)28% off.
$140.00Comparable value $140.00
(1)
Hyde II Moc Toe Loafer - Wide Width Available (Men)
NUNN BUSH

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

$44.97Current Price $44.97
(Up to 47% off)Up to 47% off.
$80.00 – $85.00Comparable value $80.00 to $85.00
(38)
Shinjuku Sandal (Men)
Birkenstock

Shinjuku Sandal (Men)

$97.48Current Price $97.48
(57% off)57% off.
$230.00Comparable value $230.00
Larkin Plain Toe Derby (Men)
Johnston & Murphy

Larkin Plain Toe Derby (Men)

$79.97Current Price $79.97
(48% off)48% off.
$155.00Comparable value $155.00
(3)
Roku Sneaker (Men)
Camper

Roku Sneaker (Men)

$129.97Current Price $129.97
(34% off)34% off.
$199.00Comparable value $199.00
Lagrange Moc Toe Loafer (Men)
ara

Lagrange Moc Toe Loafer (Men)

$79.97Current Price $79.97
(50% off)50% off.
$160.00Comparable value $160.00
GrandPro Topspin Sneaker (Men)
Cole Haan

GrandPro Topspin Sneaker (Men)

$94.97Current Price $94.97
(40% off)40% off.
$160.00Comparable value $160.00
(334)
Only a few left
Mariner 3-Eye Boat Shoe (Men)
Børn

Mariner 3-Eye Boat Shoe (Men)

$37.47 – $49.97Current Price $37.47 to $49.97
(Up to 71% off select items)Up to 71% off select items.
$130.00Comparable value $130.00
(2)
Overtime Laser Sneaker - Wide Width Available (Men)
Dockers®

Overtime Laser Sneaker - Wide Width Available (Men)

$34.97Current Price $34.97
(41% off)41% off.
$60.00Comparable value $60.00
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
(108)
Hodges Plain Toe Derby (Men)
New
Johnston & Murphy

Hodges Plain Toe Derby (Men)

$79.97Current Price $79.97
(52% off)52% off.
$169.00Comparable value $169.00
Breeze Slide Sandal (Men)
Clarks®

Breeze Slide Sandal (Men)

$49.97Current Price $49.97
(33% off)33% off.
$75.00Comparable value $75.00
City Cloud Lace-Up Sneaker (Men)
Dr. Scholl's

City Cloud Lace-Up Sneaker (Men)

$49.97Current Price $49.97
(Up to 44% off)Up to 44% off.
$85.00 – $90.00Comparable value $85.00 to $90.00
(1)
Wallabee FTR2 Moc Toe Chukka Boot (Men)
Clarks®

Wallabee FTR2 Moc Toe Chukka Boot (Men)

$79.97Current Price $79.97
(42% off)42% off.
$140.00Comparable value $140.00
Grazie Work Slip-On Sneaker - Wide Width Available (Men)
NUNN BUSH

Grazie Work Slip-On Sneaker - Wide Width Available (Men)

$69.97Current Price $69.97
(17% off)17% off.
$85.00Comparable value $85.00
Chase Mixed Media Plain Toe Derby - Wide Width Available (Men)
NUNN BUSH

Chase Mixed Media Plain Toe Derby - Wide Width Available (Men)

$49.97Current Price $49.97
(44% off)44% off.
$90.00Comparable value $90.00
(17)
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
(119)
Kore City Walk Moc Toe Slip-On Sneaker - Wide Width Available (Men)
NUNN BUSH

Kore City Walk Moc Toe Slip-On Sneaker - Wide Width Available (Men)

$49.97Current Price $49.97
(Up to 41% off)Up to 41% off.
$80.00 – $85.00Comparable value $80.00 to $85.00
(146)
Agility Peak 5 Running Shoe (Men)
Merrell

Agility Peak 5 Running Shoe (Men)

$89.97Current Price $89.97
(40% off)40% off.
$150.00Comparable value $150.00
(219)
Motion Trek Mx Sneaker (Men)
Clarks®

Motion Trek Mx Sneaker (Men)

$69.97Current Price $69.97
(30% off)30% off.
$100.00Comparable value $100.00
Upton Perforated Plain Toe Oxford (Men)
Johnston & Murphy

Upton Perforated Plain Toe Oxford (Men)

$89.97Current Price $89.97
(46% off)46% off.
$169.00Comparable value $169.00
(10)
Mullan Moc Toe Derby (Men)
New
Clarks®

Mullan Moc Toe Derby (Men)

$69.97Current Price $69.97
(46% off)46% off.
$130.00Comparable value $130.00
OriginalGrand Energyweave Wing Oxford (Men)
Cole Haan

OriginalGrand Energyweave Wing Oxford (Men)

$69.96 – $99.97Current Price $69.96 to $99.97
(Up to 61% off select items)Up to 61% off select items.
$180.00Comparable value $180.00
(8)
Leeward 2-Eye Boat Shoe (Men)
New
Sperry

Leeward 2-Eye Boat Shoe (Men)

$49.97 – $59.97Current Price $49.97 to $59.97
(Up to 56% off)Up to 56% off.
$115.00Comparable value $115.00
Essentials Arizona Waterproof Slide Sandal (Men)
New
Birkenstock

Essentials Arizona Waterproof Slide Sandal (Men)

$49.95Current Price $49.95
(766)
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