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Comfort Dress Shoes for Men

  • All Comfort
  • Boots
  • Dress Shoes
  • Loafers & Oxfords
  • Sneakers
155 items
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
(90)
Morse Grand 360 Plain Toe Derby (Men)
Cole Haan

Morse Grand 360 Plain Toe Derby (Men)

$89.96 – $99.97Current Price $89.96 to $99.97
(Up to 55% off select items)Up to 55% off select items.
$200.00Comparable value $200.00
(15)
Bedford Penny Loafer (Men)
Cole Haan

Bedford Penny Loafer (Men)

$99.97Current Price $99.97
(67% off)67% off.
$306.00Comparable value $306.00
(76)
FlexGrand 360 Plain Toe Derby (Men)
Cole Haan

FlexGrand 360 Plain Toe Derby (Men)

$89.97 – $99.97Current Price $89.97 to $99.97
(Up to 58% off)Up to 58% off.
$190.00 – $240.00Comparable value $190.00 to $240.00
(7)
Wingtip Leather Derby Sneaker (Women)
New
Cole Haan

Wingtip Leather Derby Sneaker (Women)

$99.97Current Price $99.97
(44% off)44% off.
$180.00Comparable value $180.00
(2)
Pinch Prep Penny Loafer (Men)
Cole Haan

Pinch Prep Penny Loafer (Men)

$119.97Current Price $119.97
(49% off)49% off.
$238.00Comparable value $238.00
(30)
Bedford Plain Toe Derby (Men)
Cole Haan

Bedford Plain Toe Derby (Men)

$59.97 – $99.97Current Price $59.97 to $99.97
(Up to 79% off)Up to 79% off.
$298.00 – $308.00Comparable value $298.00 to $308.00
(45)
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)
Steadwell Cap Toe Derby (Men)
Clarks®

Steadwell Cap Toe Derby (Men)

$59.97Current Price $59.97
(42% off)42% off.
$105.00Comparable value $105.00
(5)
Grand Ultra Oxford (Men)
New
Cole Haan

Grand Ultra Oxford (Men)

$89.97Current Price $89.97
(60% off)60% 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)
Monza Moc Toe Penny Loafer (Men)
Florsheim

Monza Moc Toe Penny Loafer (Men)

$79.97Current Price $79.97
(27% off)27% off.
$110.00Comparable value $110.00
(13)
OG Remastered Oxford (Men)
New
Cole Haan

OG Remastered Oxford (Men)

$89.97Current Price $89.97
(43% off)43% off.
$160.00Comparable value $160.00
(13)
Rafael Hybrid Lace-Up Derby (Men)
New
Samuel Hubbard

Rafael Hybrid Lace-Up Derby (Men)

$86.97Current Price $86.97
(61% off)61% off.
$225.00Comparable value $225.00
Only a few left
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
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)
Ledley Grand Wingtip Oxford (Men)
New
Cole Haan

Ledley Grand Wingtip Oxford (Men)

$114.97Current Price $114.97
(62% off)62% off.
$310.00Comparable value $310.00
Only a few left
'New Jersey' Slip-On
ECCO

'New Jersey' Slip-On

$89.97Current Price $89.97
(35% off)35% off.
$140.00Comparable value $140.00
(13)
Lite Hybrid Derby (Men)
ECCO

Lite Hybrid Derby (Men)

$79.97Current Price $79.97
(38% off)38% off.
$130.00Comparable value $130.00
(1)
Hodges Cap Toe Oxford (Men)
New
Johnston & Murphy

Hodges Cap Toe Oxford (Men)

$79.97Current Price $79.97
(52% off)52% off.
$169.00Comparable value $169.00
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)
American Classics Montrose Plain Toe Derby (Men)
New
Cole Haan

American Classics Montrose Plain Toe Derby (Men)

$69.97 – $99.97Current Price $69.97 to $99.97
(Up to 63% off)Up to 63% off.
$190.00 – $200.00Comparable value $190.00 to $200.00
(60)
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
(55)
ØriginalGrand CitySpectre Wholecut Shoe (Men)
New
Cole Haan

ØriginalGrand CitySpectre Wholecut Shoe (Men)

$69.97 – $99.97Current Price $69.97 to $99.97
(Up to 63% off)Up to 63% off.
$190.00Comparable value $190.00
(3)
OG Cityspectre Wholecut Oxford (Men)
New
Cole Haan

OG Cityspectre Wholecut Oxford (Men)

$99.97Current Price $99.97
(47% off)47% off.
$190.00Comparable value $190.00
Upton Wingtip Derby (Men)
New
Johnston & Murphy

Upton Wingtip Derby (Men)

$66.97 – $119.97Current Price $66.97 to $119.97
(Up to 62% off)Up to 62% off.
$169.00 – $179.00Comparable value $169.00 to $179.00
(63)
Grand Remix Oxford (Men)
Cole Haan

Grand Remix Oxford (Men)

$79.97Current Price $79.97
(60% off)60% off.
$200.00Comparable value $200.00
(13)
Only a few left
Jarvis Plain Toe Oxford - Wide Width Available (Men)
NUNN BUSH

Jarvis Plain Toe Oxford - Wide Width Available (Men)

$49.97Current Price $49.97
(Up to 44% off)Up to 44% off.
$85.00 – $90.00Comparable value $85.00 to $90.00
Whiddon Cap Toe Oxford - Wide Width Available (Men)
Clarks®

Whiddon Cap Toe Oxford - Wide Width Available (Men)

$41.96 – $59.97Current Price $41.96 to $59.97
(Up to 60% off select items)Up to 60% off select items.
$105.00Comparable value $105.00
(31)
Grand Versiq Sneaker (Men)
New
Cole Haan

Grand Versiq Sneaker (Men)

$79.97Current Price $79.97
(42% off)42% off.
$140.00Comparable value $140.00
Founder Oxford (Men)
New
Samuel Hubbard

Founder Oxford (Men)

$109.97Current Price $109.97
(62% off)62% off.
$295.00Comparable value $295.00
Only a few left
Steadwell Derby (Men)
Clarks®

Steadwell Derby (Men)

$59.97Current Price $59.97
(42% off)42% off.
$105.00Comparable value $105.00
(3)
Eon Wingtip Oxford Sneaker (Men)
New
Cole Haan

Eon Wingtip Oxford Sneaker (Men)

$109.97Current Price $109.97
(57% off)57% off.
$260.00Comparable value $260.00
(9)
ZERØGRAND Remastered Stitchlite Wingtip Oxford (Men)
Cole Haan

ZERØGRAND Remastered Stitchlite Wingtip Oxford (Men)

$109.97Current Price $109.97
(42% off)42% off.
$190.00Comparable value $190.00
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)
Barrett Braided Bit Driving Shoe (Men)
Nordstrom

Barrett Braided Bit Driving Shoe (Men)

$49.99 – $69.97Current Price $49.99 to $69.97
(Up to 44% off select items)Up to 44% off select items.
$89.95Comparable value $89.95
(28)
Carmelo Plain Toe Derby - Wide Width Available (Men)
NUNN BUSH

Carmelo Plain Toe Derby - Wide Width Available (Men)

$49.97Current Price $49.97
(44% off)44% off.
$90.00Comparable value $90.00
(18)
Radcliff Low Derby (Men)
Clarks®

Radcliff Low Derby (Men)

$79.97Current Price $79.97
(27% off)27% off.
$110.00Comparable value $110.00
Erroll Waterproof Wingtip Derby (Men)
New
Josef Seibel

Erroll Waterproof Wingtip Derby (Men)

$59.97Current Price $59.97
(65% off)65% off.
$175.00Comparable value $175.00
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
Highpoint Plain Toe Derby (Men)
Florsheim

Highpoint Plain Toe Derby (Men)

$59.97 – $69.97Current Price $59.97 to $69.97
(Up to 45% off)Up to 45% off.
$110.00Comparable value $110.00
(31)
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
(3)
Finn Derby (Men)
New
Propét

Finn Derby (Men)

$49.97Current Price $49.97
(52% off)52% off.
$104.99Comparable value $104.99
Lavoy Moc Toe Lace-Up (Men)
New
Johnston & Murphy

Lavoy Moc Toe Lace-Up (Men)

$79.97Current Price $79.97
(52% off)52% off.
$169.00Comparable value $169.00
Davidson Grand Cap Toe Oxford Sneaker (Men)
Cole Haan

Davidson Grand Cap Toe Oxford Sneaker (Men)

$119.97Current Price $119.97
(33% off)33% off.
$180.00Comparable value $180.00
Burchill Lug Sole Derby (Men)
Clarks®

Burchill Lug Sole Derby (Men)

$79.97Current Price $79.97
(20% off)20% off.
$100.00Comparable value $100.00
(2)
Stanwood Loafer (Men)
Rockport

Stanwood Loafer (Men)

$59.97Current Price $59.97
(53% off)53% off.
$130.00Comparable value $130.00
(1)
Robinsyn Waterproof Cap Toe Derby
Rockport

Robinsyn Waterproof Cap Toe Derby

$69.97Current Price $69.97
(48% off)48% off.
$135.00Comparable value $135.00
(2)
Seaver Derby - Wide Width Available (Men)
Rockport

Seaver Derby - Wide Width Available (Men)

$69.97Current Price $69.97
(46% off)46% off.
$130.00Comparable value $130.00
(1)
Erroll Waterproof Derby (Men)
New
Josef Seibel

Erroll Waterproof Derby (Men)

$59.97Current Price $59.97
(65% off)65% off.
$175.00Comparable value $175.00
Gessler Derby (Men)
Clarks®

Gessler Derby (Men)

$59.97Current Price $59.97
(36% off)36% off.
$95.00Comparable value $95.00
(4)
Larkin Wingtip Derby (Men)
Johnston & Murphy

Larkin Wingtip Derby (Men)

$79.97Current Price $79.97
(Up to 48% off)Up to 48% off.
$149.00 – $155.00Comparable value $149.00 to $155.00
(10)
Ruvo Cap Toe Derby (Men)
Florsheim

Ruvo Cap Toe Derby (Men)

$99.97Current Price $99.97
(28% off)28% off.
$140.00Comparable value $140.00
(100)
Circuit Leather Plain Toe Derby - Wide Width Available (Men)
NUNN BUSH

Circuit Leather Plain Toe Derby - Wide Width Available (Men)

$74.97Current Price $74.97
(Up to 25% off)Up to 25% off.
$90.00 – $100.00Comparable value $90.00 to $100.00
(16)
OG Cityspectre Cap Toe Oxford (Men)
New
Cole Haan

OG Cityspectre Cap Toe Oxford (Men)

$99.97Current Price $99.97
(47% off)47% off.
$190.00Comparable value $190.00
(2)
Plain Toe Derby (Men)
Cole Haan

Plain Toe Derby (Men)

$99.97Current Price $99.97
(66% off)66% off.
$298.00Comparable value $298.00
(3)
Chantry Wingtip Derby (Men)
New
Clarks®

Chantry Wingtip Derby (Men)

$69.97Current Price $69.97
(50% off)50% off.
$140.00Comparable value $140.00
(1)
Bedford Wingtip Oxford (Men)
Cole Haan

Bedford Wingtip Oxford (Men)

$99.97Current Price $99.97
(66% off)66% off.
$298.00Comparable value $298.00
(22)
Ruvo Plain Toe Leather Derby (Men)
Florsheim

Ruvo Plain Toe Leather Derby (Men)

$99.97Current Price $99.97
(31% off)31% off.
$145.00Comparable value $145.00
(27)
Keefe Cap Toe Oxford (Men)
Rockport

Keefe Cap Toe Oxford (Men)

$89.97Current Price $89.97
(30% off)30% off.
$130.00Comparable value $130.00
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
Sutton Wing Tip Derby (Men)
New
Johnston & Murphy

Sutton Wing Tip Derby (Men)

$79.97Current Price $79.97
(52% off)52% off.
$169.00Comparable value $169.00
Jenkins Plain Toe Derby (Men)
Johnston & Murphy

Jenkins Plain Toe Derby (Men)

$69.97Current Price $69.97
(55% off)55% off.
$159.00Comparable value $159.00
(17)
Metropole Milan Derby (Men)
ECCO

Metropole Milan Derby (Men)

$89.97Current Price $89.97
(51% off)51% off.
$185.00Comparable value $185.00
(2)
Ravello Leather Monk Strap Shoe (Men)
Florsheim

Ravello Leather Monk Strap Shoe (Men)

$99.97Current Price $99.97
(31% off)31% off.
$145.00Comparable value $145.00
(92)
Calderone Plain Toe Derby - Wide Width Available (Men)
NUNN BUSH

Calderone Plain Toe Derby - Wide Width Available (Men)

$54.97Current Price $54.97
(45% off)45% off.
$100.00Comparable value $100.00
(6)
Pregamo Derby (Men)
Florsheim

Pregamo Derby (Men)

$69.96Current Price $69.96
(51% off)51% off.
$145.00Comparable value $145.00
(5)
'Lenox Hill' Split Toe Derby (Men)
Cole Haan

'Lenox Hill' Split Toe Derby (Men)

$99.97Current Price $99.97
(56% off)56% off.
$230.00Comparable value $230.00
(10)
Only a few left
OriginalGrand Cityspectre Cap Toe Oxford (Men)
New
Cole Haan

OriginalGrand Cityspectre Cap Toe Oxford (Men)

$99.97Current Price $99.97
(47% off)47% off.
$190.00Comparable value $190.00
(9)
Ruvo Moc Toe Penny Loafer (Men)
Florsheim

Ruvo Moc Toe Penny Loafer (Men)

$64.98 – $99.97Current Price $64.98 to $99.97
(Up to 55% off select items)Up to 55% off select items.
$140.00 – $145.00Comparable value $140.00 to $145.00
(8)
Denali Waterproof Plain Toe Derby (Men) - Wide Width Available
NUNN BUSH

Denali Waterproof Plain Toe Derby (Men) - Wide Width Available

$94.97Current Price $94.97
(5% off)5% off.
$100.00Comparable value $100.00
(1)
Metropole London Derby (Men)
ECCO

Metropole London Derby (Men)

$119.97Current Price $119.97
(38% off)38% off.
$194.95Comparable value $194.95
(9)
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