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Men's Leather (Genuine) Comfort Dress Shoes

  • All Comfort
  • Athletic
  • Boat Shoes
  • Boots
  • Dress Shoes
  • Loafers & Slip-Ons
  • Oxfords
  • Sandals & Flip-Flops
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490 items
Erroll Waterproof Slip-On Shoe (Men)

Josef Seibel Erroll Waterproof Slip-On Shoe (Men)

$175Current Price $175
Cort 2.0 Penny Loafer (Men)

Johnston & Murphy Cort 2.0 Penny Loafer (Men)

$119 – $155Current Price $119 to $155
$149 – $155Previous Price $149 to $155
5(5)
Rucci Cap Toe Derby (Men)

Florsheim Rucci Cap Toe Derby (Men)

$130Current Price $130
5(1)
Only a few left
6 Inch Moc Toe Boot

Red Wing 6 Inch Moc Toe Boot

$319.99 – $329.99Current Price $319.99 to $329.99
4.5(651)
Jameson Chelsea Boot (Men)

Johnston & Murphy Jameson Chelsea Boot (Men)

$295Current Price $295
5(1)
Taylor Moc Toe Penny Loafer (Men)

Johnston & Murphy Taylor Moc Toe Penny Loafer (Men)

$298Current Price $298
5(8)
Lugano Slip-On Shoe (Men)

Spring Step Lugano Slip-On Shoe (Men)

$149.95Current Price $149.95
5(1)
Nigel Low Boot (Men)

Børn Nigel Low Boot (Men)

$150Current Price $150
4.1(7)
Donohue Grand Bit Driving Shoe (Men)

Cole Haan Donohue Grand Bit Driving Shoe (Men)

$160Current Price $160
Only a few left
Stuart Chukka (Men)

Josef Seibel Stuart Chukka (Men)

$175Current Price $175
'Cap Vert' Penny Loafer

Mephisto 'Cap Vert' Penny Loafer

$389Current Price $389
4.6(44)
Gold Authentic Original Boat Shoe (Men)

Sperry Gold Authentic Original Boat Shoe (Men)

$175Current Price $175
5(1)
Baldwin Penny Loafer (Men)

Johnston & Murphy Baldwin Penny Loafer (Men)

$149.99Current Price $149.99
$228Previous Price $228
2(1)
Only a few left
'London' Slip-On (Men)

Birkenstock 'London' Slip-On (Men)

$169.95 – $174.95Current Price $169.95 to $174.95
3.4(22)
'Harrison' Chukka Boot (Online Only) (Men)

Børn 'Harrison' Chukka Boot (Online Only) (Men)

$145Current Price $145
4.1(12)
Dirk Loafer (Men)

Rockport Dirk Loafer (Men)

$120Current Price $120
5(1)
Only a few left
Godney Boat Shoe (Men)

Clarks® Originals Godney Boat Shoe (Men)

$150Current Price $150
Valter Slip-On (Men)

Mephisto Valter Slip-On (Men)

$269Current Price $269
5(22)
Peppo Water Resistant Chukka Loafer (Men)

Mephisto Peppo Water Resistant Chukka Loafer (Men)

$549Current Price $549
3(3)
'Douglas' Venetian Loafer

Josef Seibel 'Douglas' Venetian Loafer

$165Current Price $165
4.9(7)
Calder Plain Toe Chelsea Boot (Men)

Johnston & Murphy Calder Plain Toe Chelsea Boot (Men)

$179Current Price $179
4(17)
Heritage R Toe Western Boot (Men)

Ariat Heritage R Toe Western Boot (Men)

$199.95Current Price $199.95
4.7(426)
Wexford Waterproof Chelsea Boot (Men)
New

Ariat Wexford Waterproof Chelsea Boot (Men)

$209.95Current Price $209.95
4.6(271)
Bernardo Water Repellent Combat Boot (Men)

Aquatalia Bernardo Water Repellent Combat Boot (Men)

$495Current Price $495
Britton Road Mid Chelsea Boot (Men)

Timberland Britton Road Mid Chelsea Boot (Men)

$160Current Price $160
4.6(40)
Only a few left
Cort Venetian Loafer (Men)

Johnston & Murphy Cort Venetian Loafer (Men)

$145 – $155Current Price $145 to $155
4.4(54)
Classic Chelsea Boot (Men)
New

Blundstone Footwear Classic Chelsea Boot (Men)

$219.95Current Price $219.95
Iron Ranger Boot (Men)

Red Wing Iron Ranger Boot (Men)

$349.99Current Price $349.99
4.5(103)
Only a few left
Tiago Perforated Loafer (Men)

Mephisto Tiago Perforated Loafer (Men)

$289Current Price $289
4.5(22)
Jarrett Bit Loafer (Men)

Spring Step Jarrett Bit Loafer (Men)

$149.95Current Price $149.95
Nigel Low Boot (Men)

Børn Nigel Low Boot (Men)

$150Current Price $150
4.1(7)
Wallabee Chukka Boot (Men)

Clarks® Originals Wallabee Chukka Boot (Men)

$170Current Price $170
Only a few left
Sorrento Monk Strap Shoe (Men)

Florsheim Sorrento Monk Strap Shoe (Men)

$130Current Price $130
Only a few left
Booker Ultra Square Toe Western Chelsea Boot (Men)

Ariat Booker Ultra Square Toe Western Chelsea Boot (Men)

$149.95Current Price $149.95
4.8(750)
Dudley Plain Toe Lug Boot (Men)

Johnston & Murphy Dudley Plain Toe Lug Boot (Men)

$285Current Price $285
4(3)
Only a few left
Original Water Resistant Chelsea Boot (Men)

Blundstone Footwear Original Water Resistant Chelsea Boot (Men)

$199.95Current Price $199.95
4.8(28)
Jakub Water Resistant Loafer (Men)

Ron White Jakub Water Resistant Loafer (Men)

$395 – $445Current Price $395 to $445
'Algoras' Slip-On

Mephisto 'Algoras' Slip-On

$229.90 – $329Current Price $229.90 to $329
$329Previous Price $329
4.4(25)
Edlef Slip-On (Men)

Mephisto Edlef Slip-On (Men)

$339Current Price $339
4.5(132)
Only a few left
Hartley Wingtip Boot (Men)

Johnston & Murphy Hartley Wingtip Boot (Men)

$325Current Price $325
Only a few left
Plain Toe Chelsea Boot (Men)

Blundstone Footwear Plain Toe Chelsea Boot (Men)

$209.95Current Price $209.95
4(4)
Abisko Leather Slip-On (Men)

Spring Step Abisko Leather Slip-On (Men)

$129.95Current Price $129.95
Only a few left
ZeroGrand Remastered Wingtip Oxford (Men)

Cole Haan ZeroGrand Remastered Wingtip Oxford (Men)

$220Current Price $220
4.8(49)
Only a few left
Berna Venetian Loafer (Men)

PIKOLINOS Berna Venetian Loafer (Men)

$190Current Price $190
4.1(8)
Conard 2.0 175th Wingtip Oxford (Men)

Johnston & Murphy Conard 2.0 175th Wingtip Oxford (Men)

$175Current Price $175
4.5(2)
Only a few left
Premium 6-Inch Waterproof Boot (Men)

Timberland Premium 6-Inch Waterproof Boot (Men)

$198Current Price $198
4.6(2724)
Only a few left
Walden Penny Loafer (Men)

Camper Walden Penny Loafer (Men)

$220Current Price $220
'San Telmo' Slip-On (Men)

PIKOLINOS 'San Telmo' Slip-On (Men)

$190Current Price $190
4.5(15)
Sandor Loafer (Men)

Børn Sandor Loafer (Men)

$135Current Price $135
Wallabee Kiltie Chukka Boot (Men)

Clarks® Originals Wallabee Kiltie Chukka Boot (Men)

$170Current Price $170
4(1)
Only a few left
Wallabee Suede Boot (Men)

Clarks® Wallabee Suede Boot (Men)

$110Current Price $110
5(2)
'Desert' Boot (Men)

Clarks® Originals 'Desert' Boot (Men)

$150Current Price $150
4.6(138)
Pegasio Water Resistant Derby (Men)

Mephisto Pegasio Water Resistant Derby (Men)

$549Current Price $549
2(4)
Authentic Original 2-Eye Boat Shoe (Men)

Sperry Authentic Original 2-Eye Boat Shoe (Men)

$100 – $110Current Price $100 to $110
Silas Water Resistant Tassel Loafer (Men)

Ron White Silas Water Resistant Tassel Loafer (Men)

$695Current Price $695
Kinser Water Resistant Plain Toe Derby (Men)

Johnston & Murphy Kinser Water Resistant Plain Toe Derby (Men)

$328Current Price $328
5(1)
Only a few left
Dillon Penny Loafer (Men)

Robert Zur Dillon Penny Loafer (Men)

$325Current Price $325
Kurtis Penny Loafer (Men)

Mephisto Kurtis Penny Loafer (Men)

$399Current Price $399
4.9(7)
Redwood Falls Chelsea Boot (Men)

Timberland Redwood Falls Chelsea Boot (Men)

$140Current Price $140
4.6(130)
Only a few left
Moc Loafer (Men)

Minnetonka Moc Loafer (Men)

$99.95Current Price $99.95
Perrin Penny Loafer (Men)

Ron White Perrin Penny Loafer (Men)

$495Current Price $495
Don Loafer (Men)

Camper Don Loafer (Men)

$184Current Price $184
$230Previous Price $230
3.5(2)
Erroll 62 Waterproof Lugged Moc Toe Derby (Men)

Josef Seibel Erroll 62 Waterproof Lugged Moc Toe Derby (Men)

$175Current Price $175
Moc Loafer (Men)

Minnetonka Moc Loafer (Men)

$99.95Current Price $99.95
Upton Penny Loafer (Men)

Johnston & Murphy Upton Penny Loafer (Men)

$99.99Current Price $99.99
$149Previous Price $149
4.7(22)
Only a few left
Original Water Resistant Chelsea Boot (Men)

Blundstone Footwear Original Water Resistant Chelsea Boot (Men)

$184.95Current Price $184.95
1(1)
Davy HydroProtect Waterproof Slip-On Men)

Mephisto Davy HydroProtect Waterproof Slip-On Men)

$339Current Price $339
4.5(15)
Berto Chukka Boot (Men)

Mephisto Berto Chukka Boot (Men)

$439Current Price $439
5(3)
Gore-Tex® Waterproof Desert Boot (Men)

Clarks® Originals Gore-Tex® Waterproof Desert Boot (Men)

$240Current Price $240
Niccolo Moc Toe Loafer (Men)

Spring Step Niccolo Moc Toe Loafer (Men)

$129.95Current Price $129.95
Norman Chukka Shoe (Men)

Camper Norman Chukka Shoe (Men)

$133Current Price $133
$185Previous Price $185
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