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Grey Comfortable Shoes for Men

  • All Comfort
  • Boots
  • Dress Shoes
  • Loafers & Oxfords
  • Sneakers
189 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 Remix Derby (Men)
Cole Haan

Grand Remix Derby (Men)

$99.97Current Price $99.97
(51% off)51% off.
$208.00Comparable value $208.00
(177)
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)
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
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)
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)
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)
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
(79)
Axton Slip-On (Men)
Nordstrom

Axton Slip-On (Men)

$69.97Current Price $69.97
(22% off)22% off.
$89.95Comparable value $89.95
(10)
Olali Flip Flop (Men)
Top Deal
OluKai

Olali Flip Flop (Men)

$59.97Current Price $59.97
(50% off)50% off.
$120.00Comparable value $120.00
(9)
Moab Speed 2 Waterproof Hiking Shoe (Men)
Merrell

Moab Speed 2 Waterproof Hiking Shoe (Men)

$99.97Current Price $99.97
(41% off)41% off.
$170.00Comparable value $170.00
(22)
Wrapt Hiking Sneaker (Men)
Merrell

Wrapt Hiking Sneaker (Men)

$69.97Current Price $69.97
(41% off)41% off.
$120.00Comparable value $120.00
(266)
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
(107)
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)
Lite Hybrid Chukka Boot (Men)
ECCO

Lite Hybrid Chukka Boot (Men)

$79.97Current Price $79.97
(42% off)42% off.
$140.00Comparable value $140.00
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 Motion Sneaker (Men)
Cole Haan

Grand Motion Sneaker (Men)

$54.98 – $55.96Current Price $54.98 to $55.96
(73% off)73% off.
$210.00Comparable value $210.00
New Markdown
(550)
Fresh Foam Roav Knit Sneaker (Men)
New
New Balance

Fresh Foam Roav Knit Sneaker (Men)

Add to Bag or Wish List to see price(135)
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)
Kyoto Desert Slide Sandal (Men)
Birkenstock

Kyoto Desert Slide Sandal (Men)

$99.97Current Price $99.97
(35% off)35% off.
$155.00Comparable value $155.00
(13)
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)
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)
Upton Knit Wingtip (Men)
Johnston & Murphy

Upton Knit Wingtip (Men)

$69.97Current Price $69.97
(55% off)55% off.
$159.00Comparable value $159.00
(25)
RC42 Sneaker (Women)
New Balance

RC42 Sneaker (Women)

$49.97 – $79.97Current Price $49.97 to $79.97
(Up to 50% off)Up to 50% off.
$99.99Comparable value $99.99
(149)
Conrad II Sneaker (Men)
Børn

Conrad II Sneaker (Men)

$63.72 – $84.97Current Price $63.72 to $84.97
(Up to 49% off select items)Up to 49% off select items.
$125.00Comparable value $125.00
(3)
Cleve 11 Low Top Slip-On Sneaker (Men)
Josef Seibel

Cleve 11 Low Top Slip-On Sneaker (Men)

$64.97Current Price $64.97
(61% off)61% off.
$170.00Comparable value $170.00
Gender Inclusive Crocs Baya Clog
CROCS

Gender Inclusive Crocs Baya Clog

Add to Bag or Wish List to see price
New Markdown
(6067)
Kore Swift Sneaker (Men)
NUNN BUSH

Kore Swift Sneaker (Men)

$32.98 – $54.97Current Price $32.98 to $54.97
(Up to 63% off select items)Up to 63% off select items.
$90.00Comparable value $90.00
New Markdown
Speed Strike 2 Hiking Boot (Men)
Merrell

Speed Strike 2 Hiking Boot (Men)

$69.97Current Price $69.97
(22% off)22% off.
$90.00Comparable value $90.00
(24)
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)
Chase Perforated Sneaker (Men)
New
Johnston & Murphy

Chase Perforated Sneaker (Men)

$79.97Current Price $79.97
(42% off)42% off.
$139.00Comparable value $139.00
(1)
Chase Plain Toe Derby (Men)
NUNN BUSH

Chase Plain Toe Derby (Men)

$54.97Current Price $54.97
(Up to 38% off)Up to 38% off.
$85.00 – $90.00Comparable value $85.00 to $90.00
(5)
515 Sneaker (Men)
New Balance

515 Sneaker (Men)

Add to Bag or Wish List to see price
New Markdown
(27)
237 Sneaker (Men)
New Balance

237 Sneaker (Men)

Add to Bag or Wish List to see price(61)
Barrett Braided Bit Driving Shoe (Men)
Nordstrom

Barrett Braided Bit Driving Shoe (Men)

$69.97Current Price $69.97
(22% off)22% off.
$89.95Comparable value $89.95
(25)
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)

$37.47 – $49.97Current Price $37.47 to $49.97
(Up to 55% off select items)Up to 55% off select items.
$80.00 – $85.00Comparable value $80.00 to $85.00
(145)
Generation ZeroGrand Stitchlite Sneaker (Men)
Cole Haan

Generation ZeroGrand Stitchlite Sneaker (Men)

$52.50 – $69.97Current Price $52.50 to $69.97
(Up to 66% off select items)Up to 66% off select items.
$155.00Comparable value $155.00
(503)
Fresh Foam X Kaiha Road Running Shoe (Men)
New Balance

Fresh Foam X Kaiha Road Running Shoe (Men)

$49.99 – $83.97Current Price $49.99 to $83.97
(Up to 52% off select items)Up to 52% off select items.
$99.99 – $104.99Comparable value $99.99 to $104.99
New Markdown
(317)
Ponte Knit Moc Toe Sneaker (Men)
NUNN BUSH

Ponte Knit Moc Toe Sneaker (Men)

$34.99 – $54.97Current Price $34.99 to $54.97
(Up to 61% off select items)Up to 61% off select items.
$90.00Comparable value $90.00
New Markdown
(4)
Kore City Walk EZ Slip-On Sneaker (Men) (Wide Width Available)
NUNN BUSH

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

$22.50 – $44.97Current Price $22.50 to $44.97
(Up to 73% off select items)Up to 73% off select items.
$85.00Comparable value $85.00
New Markdown
(19)
Grand Atlantic Oxford Derby (Men)
Cole Haan

Grand Atlantic Oxford Derby (Men)

$89.97Current Price $89.97
(59% off)59% off.
$220.00Comparable value $220.00
(2)
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
Brewski Organic Cotton Slip-On Sneaker- Wide Width Available (Men)
NUNN BUSH

Brewski Organic Cotton Slip-On Sneaker- Wide Width Available (Men)

$29.23 – $33.72Current Price $29.23 to $33.72
(Up to 65% off)Up to 65% off.
$85.00Comparable value $85.00
New Markdown
(6)
Kākaha Nia Convertible Loafer (Men)
New
OluKai

Kākaha Nia Convertible Loafer (Men)

$64.97Current Price $64.97
(50% off)50% off.
$130.00Comparable value $130.00
(31)
Barklay Canvas Derby - Wide Width Available (Men)
NUNN BUSH

Barklay Canvas Derby - Wide Width Available (Men)

$49.97 – $54.97Current Price $49.97 to $54.97
(Up to 37% off)Up to 37% off.
$80.00Comparable value $80.00
(32)
Go Walk Flex Sneaker (Men)
SKECHERS

Go Walk Flex Sneaker (Men)

$49.97Current Price $49.97
(Up to 33% off)Up to 33% off.
$70.00 – $75.00Comparable value $70.00 to $75.00
(13)
SpeedARC Matis Hiking Sneaker (Men)
Merrell

SpeedARC Matis Hiking Sneaker (Men)

$104.97 – $114.97Current Price $104.97 to $114.97
(Up to 45% off)Up to 45% off.
$180.00 – $210.00Comparable value $180.00 to $210.00
(54)
Alpine 83 Recraft Sneaker (Men)
Merrell

Alpine 83 Recraft Sneaker (Men)

$64.97 – $69.97Current Price $64.97 to $69.97
(Up to 45% off)Up to 45% off.
$110.00 – $120.00Comparable value $110.00 to $120.00
(199)
OOcoozie Sport Workhorse Recovery Mule (Men)
Oofos

OOcoozie Sport Workhorse Recovery Mule (Men)

$49.98Current Price $49.98
(56% off)56% off.
$114.95Comparable value $114.95
New Markdown
(3)
Relaxed Fit Slip-In Sneaker (Men)
SKECHERS

Relaxed Fit Slip-In Sneaker (Men)

$49.97Current Price $49.97
(44% off)44% off.
$90.00Comparable value $90.00
Fresh Foam X 1080v14 Running Shoe (Men)
New Balance

Fresh Foam X 1080v14 Running Shoe (Men)

$64.98 – $99.97Current Price $64.98 to $99.97
(Up to 60% off select items)Up to 60% off select items.
$164.99Comparable value $164.99
New Markdown
(1138)
Island Hopper Convertible Sneaker (Men)
New
OluKai

Island Hopper Convertible Sneaker (Men)

$69.97Current Price $69.97
(53% off)53% off.
$150.00Comparable value $150.00
(32)
Gender Inclusive Made in USA 996 V1 Sneaker
Top Deal
New Balance

Gender Inclusive Made in USA 996 V1 Sneaker

$79.97Current Price $79.97
(54% off)54% off.
$174.99Comparable value $174.99
(101)
Fresh Foam X 1080 v14 Running Shoe (Men)
New Balance

Fresh Foam X 1080 v14 Running Shoe (Men)

$53.98 – $99.97Current Price $53.98 to $99.97
(Up to 67% off select items)Up to 67% off select items.
$164.99Comparable value $164.99
New Markdown
(1135)
Tayton Step Activated Sneaker (Men)
Rockport

Tayton Step Activated Sneaker (Men)

$29.96Current Price $29.96
(75% off)75% off.
$120.00Comparable value $120.00
New Markdown
(3)
Oswego Slip-On Sneaker (Men)
Birkenstock

Oswego Slip-On Sneaker (Men)

$64.98Current Price $64.98
(56% off)56% off.
$150.00Comparable value $150.00
New Markdown
(1)
Bend Decon Sneaker (Men)
Birkenstock

Bend Decon Sneaker (Men)

$64.98Current Price $64.98
(59% off)59% off.
$160.00Comparable value $160.00
New Markdown
(2)
Kore Swift Derby (Men)
NUNN BUSH

Kore Swift Derby (Men)

$69.97Current Price $69.97
(26% off)26% off.
$95.00Comparable value $95.00
Craftwell Sneaker (Men)
Clarks®

Craftwell Sneaker (Men)

$64.97 – $79.97Current Price $64.97 to $79.97
(Up to 35% off)Up to 35% off.
$100.00Comparable value $100.00
(1)
680 Running Shoe - Multiple Widths Available (Men)
New Balance

680 Running Shoe - Multiple Widths Available (Men)

Add to Bag or Wish List to see price(438)
Grand Hurrion Wingtip Derby (Men)
Cole Haan

Grand Hurrion Wingtip Derby (Men)

$99.97Current Price $99.97
(56% off)56% off.
$230.00Comparable value $230.00
(25)
Fresh Foam Arishi v4 Running Shoe (Men)
New Balance

Fresh Foam Arishi v4 Running Shoe (Men)

$59.97 – $63.97Current Price $59.97 to $63.97
(Up to 25% off)Up to 25% off.
$69.99 – $79.99Comparable value $69.99 to $79.99
(122)
Fortino Water Repellent Boot (Men)
Aquatalia

Fortino Water Repellent Boot (Men)

$259.97Current Price $259.97
(58% off)58% off.
$625.00Comparable value $625.00
(3)
Kore City Rally Low Top Sneaker (Men)
NUNN BUSH

Kore City Rally Low Top Sneaker (Men)

$54.97Current Price $54.97
(35% off)35% off.
$85.00Comparable value $85.00
Neilson Sneaker (Men)
New
Dockers®

Neilson Sneaker (Men)

$59.97Current Price $59.97
(33% off)33% off.
$90.00Comparable value $90.00
Griff Plain Toe Derby (Men)
NUNN BUSH

Griff Plain Toe Derby (Men)

$59.97 – $89.97Current Price $59.97 to $89.97
(Up to 40% off)Up to 40% off.
$100.00 – $110.00Comparable value $100.00 to $110.00
(1)
Kore City Rally Low Top Sneaker (Men)
NUNN BUSH

Kore City Rally Low Top Sneaker (Men)

$54.97Current Price $54.97
(35% off)35% 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)

$54.97Current Price $54.97
(38% off)38% off.
$90.00Comparable value $90.00
(17)
Equalizer 5.0 Slip-On Sneaker (Men)
SKECHERS

Equalizer 5.0 Slip-On Sneaker (Men)

$32.48Current Price $32.48
(53% off)53% off.
$70.00Comparable value $70.00
New Markdown
(31)
Un Briley Step Slip-On Loafer (Men)
New
Clarks®

Un Briley Step Slip-On Loafer (Men)

$79.97Current Price $79.97
(50% off)50% off.
$160.00Comparable value $160.00
Fresh Foam X 840v1 Sneaker (Men)
New Balance

Fresh Foam X 840v1 Sneaker (Men)

$69.97Current Price $69.97
(50% off)50% off.
$139.99Comparable value $139.99
(155)
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