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Comfort Dress Shoes for Men

  • All Comfort
  • Boots
  • Dress Shoes
  • Loafers & Oxfords
  • Sneakers
154 items
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
(14)
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)
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
(7)
Bedford Penny Loafer (Men)
Cole Haan

Bedford Penny Loafer (Men)

$99.97Current Price $99.97
(67% off)67% off.
$306.00Comparable value $306.00
(74)
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)
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)
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
(9)
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
<p>Grand Versiq Sneaker (Men)</p>
New
Cole Haan

Grand Versiq Sneaker (Men)

$79.97Current Price $79.97
(42% off)42% off.
$140.00Comparable value $140.00
ØriginalGrand CitySpectre Wholecut Shoe (Men)
New
Cole Haan

ØriginalGrand CitySpectre Wholecut Shoe (Men)

$99.97Current Price $99.97
(47% off)47% off.
$190.00Comparable value $190.00
(3)
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
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)
Grand 360 Cap Toe Derby (Men)
New
Cole Haan

Grand 360 Cap Toe Derby (Men)

$74.96 – $89.97Current Price $74.96 to $89.97
(Up to 68% off select items)Up to 68% off select items.
$190.00 – $240.00Comparable value $190.00 to $240.00
(26)
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
(87)
Lite Hybrid Derby (Men)
ECCO

Lite Hybrid Derby (Men)

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

Bolivar Cap Toe Sneaker (Men)

$99.97Current Price $99.97
(63% off)63% off.
$275.00Comparable value $275.00
Only a few left
Hodges Knit Derby (Men)
Johnston & Murphy

Hodges Knit Derby (Men)

$59.97Current Price $59.97
(64% off)64% off.
$169.00Comparable value $169.00
(1)
Wallabee Weave Loafer (Men)
New
Clarks®

Wallabee Weave Loafer (Men)

$89.97Current Price $89.97
(50% off)50% off.
$180.00Comparable value $180.00
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
ZERØGRAND Remastered Stitchlite Wingtip Oxford (Men)
New
Cole Haan

ZERØGRAND Remastered Stitchlite Wingtip Oxford (Men)

$109.97Current Price $109.97
(42% off)42% off.
$190.00Comparable value $190.00
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)
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)
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)
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
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
Acklen Plain Toe Derby (Men)
New
Johnston & Murphy

Acklen Plain Toe Derby (Men)

$69.97Current Price $69.97
(51% off)51% off.
$145.00Comparable value $145.00
'Lenox Hill' Cap Toe Derby (Men)
New
Cole Haan

'Lenox Hill' Cap Toe Derby (Men)

$109.97Current Price $109.97
(52% off)52% off.
$230.00Comparable value $230.00
(82)
Pregamo II Moc Toe Horsebit Loafer (Men)
Florsheim

Pregamo II Moc Toe Horsebit Loafer (Men)

$99.97Current Price $99.97
(31% off)31% off.
$145.00Comparable value $145.00
(3)
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)
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
<p>Torlite Lo Moc Toe Oxford (Men)</p>
New
Clarks®

Torlite Lo Moc Toe Oxford (Men)

$69.97Current Price $69.97
(41% off)41% off.
$120.00Comparable value $120.00
Radcliff Derby (Men)
Clarks®

Radcliff Derby (Men)

$59.97Current Price $59.97
(40% off)40% off.
$100.00Comparable value $100.00
Only a few left
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
(99)
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
(9)
Braydon Knit Plain Toe Derby (Men)
Johnston & Murphy

Braydon Knit Plain Toe Derby (Men)

$59.97Current Price $59.97
(56% off)56% off.
$139.00Comparable value $139.00
(42)
x Colour Plus Companie Genuine Calf Hair 3-Eye Boat Shoe (Men)
New
Sperry

x Colour Plus Companie Genuine Calf Hair 3-Eye Boat Shoe (Men)

$92.97Current Price $92.97
(62% off)62% off.
$250.00Comparable value $250.00
Pregamo Derby (Men)
Florsheim

Pregamo Derby (Men)

$69.96Current Price $69.96
(51% off)51% off.
$145.00Comparable value $145.00
(5)
Classic Moc II Driving Shoe (Men)
ECCO

Classic Moc II Driving Shoe (Men)

$67.47 – $89.97Current Price $67.47 to $89.97
(Up to 51% off select items)Up to 51% off select items.
$140.00Comparable value $140.00
(112)
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)
Grand Remix Oxford (Men)
Cole Haan

Grand Remix Oxford (Men)

$79.97Current Price $79.97
(60% off)60% off.
$200.00Comparable value $200.00
(12)
Only a few left
Queenstown Penny Loafer (Men)
ECCO

Queenstown Penny Loafer (Men)

$99.97Current Price $99.97
(28% off)28% off.
$140.00Comparable value $140.00
(1)
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)
Taylor Moc Toe Penny Loafer (Men)
Johnston & Murphy

Taylor Moc Toe Penny Loafer (Men)

$89.97Current Price $89.97
(69% off)69% off.
$298.00Comparable value $298.00
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
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)
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)
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)
Stanwood Loafer (Men)
Rockport

Stanwood Loafer (Men)

$59.97Current Price $59.97
(53% off)53% off.
$130.00Comparable value $130.00
Modern Essentials Wingtip Oxford (Men)
Cole Haan

Modern Essentials Wingtip Oxford (Men)

$76.96Current Price $76.96
(74% off)74% off.
$298.00Comparable value $298.00
(5)
Aldwin Derby (Men)
New
Clarks®

Aldwin Derby (Men)

$69.97Current Price $69.97
(36% off)36% off.
$110.00Comparable value $110.00
FlexGrand 360 Plain Toe Derby (Men)
New
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)
Jenson Longwing Derby (Men)
New
Johnston & Murphy

Jenson Longwing Derby (Men)

$109.97Current Price $109.97
(62% off)62% off.
$295.00Comparable value $295.00
(3)
Only a few left
Finn Derby (Men)
New
Propét

Finn Derby (Men)

$49.97Current Price $49.97
(52% off)52% off.
$104.99Comparable value $104.99
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)
Pregamo Moc Toe Bit Loafer (Men)
Florsheim

Pregamo Moc Toe Bit Loafer (Men)

$99.97Current Price $99.97
(31% off)31% off.
$145.00Comparable value $145.00
Upton Perforated Plain Toe Derby (Men)
New
Johnston & Murphy

Upton Perforated Plain Toe Derby (Men)

$54.97Current Price $54.97
(63% off)63% off.
$149.00Comparable value $149.00
(9)
Only a few left
Dayton Driving Penny Loafer (Men)
Johnston & Murphy

Dayton Driving Penny Loafer (Men)

$89.97Current Price $89.97
(63% off)63% off.
$245.00Comparable value $245.00
(9)
Fermo Plain Toe Leather Derby (Men)
Florsheim

Fermo Plain Toe Leather Derby (Men)

$59.97Current Price $59.97
(53% off)53% off.
$130.00Comparable value $130.00
(6)
Newmark Grand Cap Toe Oxford (Men)
Cole Haan

Newmark Grand Cap Toe Oxford (Men)

$119.97Current Price $119.97
(61% off)61% off.
$308.00Comparable value $308.00
Whiddon Pace Derby - Wide Width Available (Men)
Clarks®

Whiddon Pace Derby - Wide Width Available (Men)

$59.97Current Price $59.97
(36% off)36% off.
$95.00Comparable value $95.00
(10)
Upton Wingtip Derby (Men)
Johnston & Murphy

Upton Wingtip Derby (Men)

$119.97Current Price $119.97
(29% off)29% off.
$169.00Comparable value $169.00
(11)
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
Egan Saddle Derby (Men)
Dockers®

Egan Saddle Derby (Men)

$59.97Current Price $59.97
(33% off)33% off.
$90.00Comparable value $90.00
Radcliff Plain Toe Derby (Men)
Clarks®

Radcliff Plain Toe Derby (Men)

$79.97Current Price $79.97
(27% off)27% off.
$110.00Comparable value $110.00
Archer Cap Toe Derby (Men)
Johnston & Murphy

Archer Cap Toe Derby (Men)

$69.97Current Price $69.97
(49% off)49% off.
$139.00Comparable value $139.00
(3)
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)
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)
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