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Comfort Dress Shoes for Men

  • All Comfort
  • Boots
  • Dress Shoes
  • Loafers & Oxfords
  • Sneakers
150 items
Morse Grand 360 Plain Toe Derby
Clear The Rack
Cole Haan

Morse Grand 360 Plain Toe Derby

$48.73 – $99.97Current Price $48.73 to $99.97
(Extra 25% off select items)Includes extra 25% off select items.
$64.98Previous Price $64.98
$200.00Comparable value $200.00
(18)
Larkin Wingtip Derby
Johnston & Murphy

Larkin Wingtip Derby

$79.97Current Price $79.97
(48% off)48% off.
$155.00Comparable value $155.00
(11)
Bedford Cap Toe Derby
Cole Haan

Bedford Cap Toe Derby

$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
(94)
FlexGrand 360 Plain Toe Derby
Clear The Rack
Cole Haan

FlexGrand 360 Plain Toe Derby

$43.86 – $99.97Current Price $43.86 to $99.97
(Extra 25% off select items)Includes extra 25% off select items.
$58.48 – $64.98Previous Price $58.48 to $64.98
$190.00 – $240.00Comparable value $190.00 to $240.00
New Markdown
(7)
Steadwell Cap Toe Derby
Clarks®

Steadwell Cap Toe Derby

$59.97Current Price $59.97
(42% off)42% off.
$105.00Comparable value $105.00
(6)
Bedford Penny Loafer
Cole Haan

Bedford Penny Loafer

$99.97Current Price $99.97
(67% off)67% off.
$306.00Comparable value $306.00
(79)
Garett Wingtip
Rockport

Garett Wingtip

$89.95Current Price $89.95
(28% off)28% off.
$125.00Comparable value $125.00
(8)
Davidson Grand Cap Toe Oxford Sneaker
Cole Haan

Davidson Grand Cap Toe Oxford Sneaker

$119.97Current Price $119.97
(33% off)33% off.
$180.00Comparable value $180.00
Brody Driving Penny Loafer
Clear The Rack
Nordstrom

Brody Driving Penny Loafer

$26.23 – $69.97Current Price $26.23 to $69.97
(Extra 25% off select items)Includes extra 25% off select items.
$34.98Previous Price $34.98
$89.95 – $99.95Comparable value $89.95 to $99.95
(152)
'New Jersey' Slip-On
ECCO

'New Jersey' Slip-On

$89.97Current Price $89.97
(35% off)35% off.
$140.00Comparable value $140.00
(13)
OriginalGrand Cityspectre Cap Toe Oxford
New
Cole Haan

OriginalGrand Cityspectre Cap Toe Oxford

$72.97 – $99.97Current Price $72.97 to $99.97
(Up to 61% off)Up to 61% off.
$190.00Comparable value $190.00
(1)
Circuit Leather Plain Toe Derby - Wide Width Available
NUNN BUSH

Circuit Leather Plain Toe Derby - Wide Width Available

$74.97Current Price $74.97
(25% off)25% off.
$100.00Comparable value $100.00
(16)
Steadwell Derby
New
Clarks®

Steadwell Derby

$59.97Current Price $59.97
(42% off)42% off.
$105.00Comparable value $105.00
(3)
Grand Shadowlite Wingtip Derby
Cole Haan

Grand Shadowlite Wingtip Derby

$99.97Current Price $99.97
(50% off)50% off.
$200.00Comparable value $200.00
(1)
Bedford Plain Toe Derby
Cole Haan

Bedford Plain Toe Derby

$59.97 – $99.97Current Price $59.97 to $99.97
(Up to 79% off)Up to 79% off.
$298.00 – $313.00Comparable value $298.00 to $313.00
(45)
Griff Cap Toe Oxford - Wide Width Available
New
NUNN BUSH

Griff Cap Toe Oxford - Wide Width Available

$89.97Current Price $89.97
(18% off)18% off.
$110.00Comparable value $110.00
OG Cityspectre Wholecut Oxford
Cole Haan

OG Cityspectre Wholecut Oxford

$99.97Current Price $99.97
(47% off)47% off.
$190.00Comparable value $190.00
FLORSHEIM Ruvo Cap Toe Derby
Florsheim

FLORSHEIM Ruvo Cap Toe Derby

$99.97Current Price $99.97
(28% off)28% off.
$140.00Comparable value $140.00
(102)
Hodges Knit Derby
Johnston & Murphy

Hodges Knit Derby

$59.97Current Price $59.97
(64% off)64% off.
$169.00Comparable value $169.00
(1)
'Lenox Hill' Cap Toe Derby
Clear The Rack
Cole Haan

'Lenox Hill' Cap Toe Derby

$53.61 – $109.97Current Price $53.61 to $109.97
(Extra 25% off select items)Includes extra 25% off select items.
$71.48Previous Price $71.48
$230.00Comparable value $230.00
(82)
Newmark Grand Penny Loafer
New
Cole Haan

Newmark Grand Penny Loafer

$119.97Current Price $119.97
(61% off)61% off.
$308.00Comparable value $308.00
(3)
Hodges Plain Toe Derby
Johnston & Murphy

Hodges Plain Toe Derby

$79.97Current Price $79.97
(52% off)52% off.
$169.00Comparable value $169.00
Upton Wingtip Derby
Clear The Rack
Johnston & Murphy

Upton Wingtip Derby

$67.47 – $119.97Current Price $67.47 to $119.97
(Extra 25% off select items)Includes extra 25% off select items.
$89.96Previous Price $89.96
$169.00Comparable value $169.00
(64)
Pregamo II Moc Toe Horsebit Loafer
Florsheim

Pregamo II Moc Toe Horsebit Loafer

$99.97Current Price $99.97
(31% off)31% off.
$145.00Comparable value $145.00
(3)
Fallo Wingtip Derby
Clear The Rack
Rockport

Fallo Wingtip Derby

$34.11Current Price $34.11
(Extra 25% off)Includes extra 25% off.
$45.48Previous Price $45.48
$130.00Comparable value $130.00
New Markdown
Egan Saddle Derby
Dockers®

Egan Saddle Derby

$59.97Current Price $59.97
(33% off)33% off.
$90.00Comparable value $90.00
Jarvis Moc Toe Slip-On Loafer - Wide Width Available
NUNN BUSH

Jarvis Moc Toe Slip-On Loafer - Wide Width Available

$49.97Current Price $49.97
(Up to 44% off)Up to 44% off.
$85.00 – $90.00Comparable value $85.00 to $90.00
(1)
Judson Grand Wingtip Derby
New
Cole Haan

Judson Grand Wingtip Derby

$85.97Current Price $85.97
(61% off)61% off.
$225.00Comparable value $225.00
(4)
Chantry Wingtip Derby
Clarks®

Chantry Wingtip Derby

$69.97Current Price $69.97
(50% off)50% off.
$140.00Comparable value $140.00
(1)
ØriginalGrand CitySpectre Wholecut Shoe
Clear The Rack
Cole Haan

ØriginalGrand CitySpectre Wholecut Shoe

$36.72 – $99.97Current Price $36.72 to $99.97
(Extra 25% off select items)Includes extra 25% off select items.
$48.96Previous Price $48.96
$190.00Comparable value $190.00
New Markdown
(3)
Monza Moc Toe Penny Loafer
Florsheim

Monza Moc Toe Penny Loafer

$79.97Current Price $79.97
(27% off)27% off.
$110.00Comparable value $110.00
(13)
Stanwood Loafer
Rockport

Stanwood Loafer

$59.97Current Price $59.97
(53% off)53% off.
$130.00Comparable value $130.00
(1)
Newmark Grand Plain Toe Derby
Cole Haan

Newmark Grand Plain Toe Derby

$119.97Current Price $119.97
(61% off)61% off.
$308.00Comparable value $308.00
(4)
Jenson Longwing Derby
New
Johnston & Murphy

Jenson Longwing Derby

$109.97Current Price $109.97
(62% off)62% off.
$295.00Comparable value $295.00
Only a few left
Burchill Lug Sole Derby
Clear The Rack
Clarks®

Burchill Lug Sole Derby

$35.98Current Price $35.98
(Extra 25% off)Includes extra 25% off.
$47.98Previous Price $47.98
$100.00Comparable value $100.00
(2)
Seaver Derby - Wide Width Available
Clear The Rack
Rockport

Seaver Derby - Wide Width Available

$34.11Current Price $34.11
(Extra 25% off)Includes extra 25% off.
$45.48Previous Price $45.48
$130.00Comparable value $130.00
New Markdown
(1)
American Classics Montrose Plain Toe Derby
Cole Haan

American Classics Montrose Plain Toe Derby

$69.97Current Price $69.97
(63% off)63% off.
$190.00Comparable value $190.00
(15)
Queenstown Penny Loafer
Clear The Rack
ECCO

Queenstown Penny Loafer

$48.73Current Price $48.73
(Extra 25% off)Includes extra 25% off.
$64.98Previous Price $64.98
$140.00Comparable value $140.00
(1)
Barrett Braided Bit Driving Shoe
Clear The Rack
Nordstrom

Barrett Braided Bit Driving Shoe

$26.23 – $69.97Current Price $26.23 to $69.97
(Extra 25% off select items)Includes extra 25% off select items.
$34.98Previous Price $34.98
$89.95Comparable value $89.95
(33)
Grand Versiq Sneaker
Cole Haan

Grand Versiq Sneaker

$79.97Current Price $79.97
(42% off)42% off.
$140.00Comparable value $140.00
(1)
Grand Atlantic Oxford Derby
Cole Haan

Grand Atlantic Oxford Derby

$89.97Current Price $89.97
(59% off)59% off.
$220.00Comparable value $220.00
(2)
Braydon Knit Plain Toe Derby
Johnston & Murphy

Braydon Knit Plain Toe Derby

$59.97Current Price $59.97
(56% off)56% off.
$139.00Comparable value $139.00
(42)
Nelson Wingtip Derby - Wide Width Available
NUNN BUSH

Nelson Wingtip Derby - Wide Width Available

$89.97Current Price $89.97
(28% off)28% off.
$125.00Comparable value $125.00
Eon Wingtip Oxford Sneaker
Cole Haan

Eon Wingtip Oxford Sneaker

$109.97Current Price $109.97
(57% off)57% off.
$260.00Comparable value $260.00
(9)
Hodges Plain Toe Oxford
Johnston & Murphy

Hodges Plain Toe Oxford

$79.97Current Price $79.97
(52% off)52% off.
$169.00Comparable value $169.00
Sorrello Cap Toe Balmoral Oxford
Florsheim

Sorrello Cap Toe Balmoral Oxford

$99.97Current Price $99.97
(31% off)31% off.
$145.00Comparable value $145.00
(58)
Wingtip Leather Derby Sneaker
Cole Haan

Wingtip Leather Derby Sneaker

$99.97Current Price $99.97
(44% off)44% off.
$180.00Comparable value $180.00
(1)
Center Cap Toe Derby - Wide Width Available
Florsheim

Center Cap Toe Derby - Wide Width Available

$89.97Current Price $89.97
(35% off)35% off.
$140.00Comparable value $140.00
(52)
Barklay Canvas Derby - Wide Width Available
NUNN BUSH

Barklay Canvas Derby - Wide Width Available

$49.97 – $54.97Current Price $49.97 to $54.97
(Up to 37% off)Up to 37% off.
$80.00Comparable value $80.00
(32)
Carmelo Plain Toe Derby - Wide Width Available
NUNN BUSH

Carmelo Plain Toe Derby - Wide Width Available

$49.97Current Price $49.97
(44% off)44% off.
$90.00Comparable value $90.00
(18)
Highpoint Plain Toe Derby
Florsheim

Highpoint Plain Toe Derby

$59.97 – $69.97Current Price $59.97 to $69.97
(Up to 45% off)Up to 45% off.
$110.00Comparable value $110.00
(31)
Cooper Bit Loafer
New
Nordstrom

Cooper Bit Loafer

$69.97Current Price $69.97
(46% off)46% off.
$129.95Comparable value $129.95
(2)
Howard Wingtip Oxford
Clear The Rack
Clarks®

Howard Wingtip Oxford

$29.23Current Price $29.23
(Extra 25% off)Includes extra 25% off.
$38.98Previous Price $38.98
$110.00Comparable value $110.00
New Markdown
(1)
Grand 360 Cap Toe Derby
Clear The Rack
Cole Haan

Grand 360 Cap Toe Derby

$56.22 – $89.97Current Price $56.22 to $89.97
(Extra 25% off select items)Includes extra 25% off select items.
$74.96Previous Price $74.96
$190.00 – $240.00Comparable value $190.00 to $240.00
(26)
Hodges Cap Toe Oxford
Johnston & Murphy

Hodges Cap Toe Oxford

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

Radcliff Derby

$59.97Current Price $59.97
(40% off)40% off.
$100.00Comparable value $100.00
Only a few left
Aldwin Derby
Clarks®

Aldwin Derby

$69.97Current Price $69.97
(36% off)36% off.
$110.00Comparable value $110.00
Wedgewood Plain Toe Derby - Wide Width Available
NUNN BUSH

Wedgewood Plain Toe Derby - Wide Width Available

$49.97Current Price $49.97
(41% off)41% off.
$85.00Comparable value $85.00
(1)
Larkin Plain Toe Derby
Johnston & Murphy

Larkin Plain Toe Derby

$79.97Current Price $79.97
(48% off)48% off.
$155.00Comparable value $155.00
(4)
Ruvo Moc Toe Penny Loafer
Clear The Rack
Florsheim

Ruvo Moc Toe Penny Loafer

$48.73 – $99.97Current Price $48.73 to $99.97
(Extra 25% off select items)Includes extra 25% off select items.
$64.98Previous Price $64.98
$140.00 – $145.00Comparable value $140.00 to $145.00
(8)
Jenkins Plain Toe Derby
Johnston & Murphy

Jenkins Plain Toe Derby

$69.97Current Price $69.97
(55% off)55% off.
$159.00Comparable value $159.00
(17)
Lite Hybrid Derby
Clear The Rack
ECCO

Lite Hybrid Derby

$44.97 – $79.97Current Price $44.97 to $79.97
(Extra 25% off select items)Includes extra 25% off select items.
$59.96Previous Price $59.96
$130.00Comparable value $130.00
(1)
Dayton Driving Penny Loafer
Johnston & Murphy

Dayton Driving Penny Loafer

$89.97Current Price $89.97
(63% off)63% off.
$245.00Comparable value $245.00
(9)
Only a few left
Calderone Plain Toe Derby - Wide Width Available
NUNN BUSH

Calderone Plain Toe Derby - Wide Width Available

$54.97Current Price $54.97
(45% off)45% off.
$100.00Comparable value $100.00
(6)
Pregamo Moc Toe Bit Loafer
Florsheim

Pregamo Moc Toe Bit Loafer

$89.97Current Price $89.97
(37% off)37% off.
$145.00Comparable value $145.00
(63)
OG Remastered Oxford
Cole Haan

OG Remastered Oxford

$89.97Current Price $89.97
(43% off)43% off.
$160.00Comparable value $160.00
(1)
Cadet Plain Toe Oxford
NUNN BUSH

Cadet Plain Toe Oxford

$49.97Current Price $49.97
(Up to 47% off)Up to 47% off.
$85.00 – $95.00Comparable value $85.00 to $95.00
(13)
Radcliff Low Derby
Clarks®

Radcliff Low Derby

$79.97Current Price $79.97
(27% off)27% off.
$110.00Comparable value $110.00
ZERØGRAND Remastered Stitchlite Wingtip Oxford
Cole Haan

ZERØGRAND Remastered Stitchlite Wingtip Oxford

$109.97Current Price $109.97
(42% off)42% off.
$190.00Comparable value $190.00
Grand Ultra Oxford
Cole Haan

Grand Ultra Oxford

$89.97Current Price $89.97
(60% off)60% off.
$230.00Comparable value $230.00
Only a few left
KORE EZ Hero Hands-Free Plain Toe Oxford - Wide Width Available
Clear The Rack
NUNN BUSH

KORE EZ Hero Hands-Free Plain Toe Oxford - Wide Width Available

$36.54 – $64.97Current Price $36.54 to $64.97
(Extra 25% off select items)Includes extra 25% off select items.
$48.72Previous Price $48.72
$95.00Comparable value $95.00
New Markdown
(1)
Earl Plain Toe Derby
Josef Seibel

Earl Plain Toe Derby

$59.97Current Price $59.97
(64% off)64% off.
$170.00Comparable value $170.00
(2)
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