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Comfort
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    Featured

  • Dress Shoes

Men's Comfort Dress Shoes

129 items
Product Image

Nordstrom David Chelsea Boot (Men)

Was:$134.95
Now:$79.9041% off
(26)
Free Delivery
Product Image
New Markdown

Nordstrom Gavin Waterproof Chelsea Boot (Men)

Was:$129.95
Now:$77.9640% off
(6)
Free Delivery
Product Image

Nordstrom Remy Monk Strap Slip-On (Men)

Was:$99.95
Now:$49.9850% off
(14)
Free Delivery
Product Image

Nordstrom Men's Shop Vincent Plain Toe Derby (Men)

Was:$99.95
Now:$49.9850% off
(7)
Free Delivery
Product Image

ECCO Melbourne Chukka Boot (Men)

Was:$169.95
Now:$99.9041% off
(1)
Free Delivery
Product Image

Cole Haan Wakefield Grand Waterproof Chelsea Boot (Men)

Was:$200.00
Now:$120.0040% off
(16)
Free Delivery
Product Image
New Markdown

Nordstrom Gavin Waterproof Chelsea Boot (Men)

Was:$129.95
Now:$77.9040% off
(6)
Free Delivery
Product Image

Blundstone Classic 550 Series Water Resistant Chelsea Boot (Men)

$199.95
(2)
Free Delivery
Product Image

Cole Haan 2.ZeroGrand Stitchlite Water Resistant Wingtip (Men)

Was:$200.00
Now:$99.9050% off
(63)
Free Delivery
Product Image

ECCO Melbourne Chukka Boot (Men)

Was:$169.95
Now:$99.9041% off
(1)
Free Delivery
Product Image

ECCO Classic Moc II Venetian Loafer (Men)

Was:$160.00
Now:$99.9038% off
(96)
Free Delivery
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Product Image

Nordstrom Samson Waterproof Chelsea Boot (Men)

Was:$129.95
Now:$77.9640% off
Free Delivery
Product Image

Cole Haan 'Tucker Venetian' Loafer

Was:$150.00
Now:$74.9050% off
(257)
Free Delivery
Product Image

Cole Haan Warren Cap Toe Derby (Men)

Was:$200.00
Now:$99.9050% off
(138)
Free Delivery
Product Image

Cole Haan Richardson Cap Toe Derby (Men)

Was:$180.00
Now:$107.9040% off
(12)
Free Delivery
Product Image

Blundstone Water Resistant Chelsea Boot (Men)

$194.95
Free Delivery
Product Image
New Markdown

Cole Haan 'Tucker Venetian' Loafer

Was:$150.00
Now:$74.9050% off
(257)
Free Delivery
Product Image

Blondo Grant Waterproof Chelsea Boot (Men)

$149.95
(10)
Free Delivery
Product Image
New Markdown

Cole Haan 2.ZeroGrand Stitchlite Water Resistant Wingtip (Men)

Was:$200.00
Now:$99.9050% off
(63)
Free Delivery
Buy online, pick up in store.
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Product Image
New Markdown

Clarks® Foxwell Top Chelsea Boot (Men)

Was:$140.00
Now:$74.4747% off
Free Delivery
Product Image
New Markdown

Nordstrom David Water Resistant Chelsea Boot (Men)

Was:$134.95
Now:$67.4850% off
Free Delivery
Product Image

Rockport 'Evander' Oxford

Was:$109.95
Now:$79.0028% off
(14)
Free Delivery
Product Image

ECCO Helsinki Bike Toe Slip-On (Men)

$159.95 – $160.00
(98)
Free Delivery
Product Image

Florsheim Tux Plain Toe Derby (Men)

$114.95
(8)
Free Delivery
Product Image

Geox New Damon 2 Venetian Slip-On Shoe (Men)

$130.00
Free Delivery
Product Image

ECCO Holton Apron Toe Derby (Men)

$189.95
(25)
Free Delivery
Product Image

UGG® Butte Waterproof Chelsea Boot (Men)

$179.95
(8)
Free Delivery
Product Image

Florsheim Cardinelli Wingtip (Men)

$99.95
(3)
Free Delivery
Product Image

ECCO ST.1 Hybrid Lite Cap Toe Boot (Men)

Was:$199.95
Now:$129.9035% off
(1)
Free Delivery
Product Image

ECCO Melbourne Plain Toe Derby (Men)

$149.95
Free Delivery
Product Image

Florsheim Uptown Cap Toe Derby (Men)

$114.95
Free Delivery
Product Image

Johnston & Murphy Bradford Cap Toe Derby (Men)

$129.99
(5)
Free Delivery
Product Image
New Markdown

Magnanni Romelo Diversa Apron Toe Derby (Men)

Was:$350.00
Now:$210.0040% off
(8)
Free Delivery
Product Image

Blondo Laurence Waterproof Boot (Men)

$169.95
(2)
Free Delivery
Product Image

Florsheim Midtown Waterproof Chukka Boot (Men)

$125.00
(11)
Free Delivery
Product Image

Geox New Damon 1 Slip-On Penny Loafer (Men)

$130.00
Free Delivery
Product Image

Rockport 'Essential Details' Waterproof Derby

Was:$109.95
Now:$99.959% off
(2)
Free Delivery
Product Image

Dunham Clyde Chelsea Boot (Men)

$170.00
Free Delivery
Product Image

ECCO Melbourne Venetian Loafer (Men)

$149.95
(2)
Free Delivery
Product Image
New!

Trask Lawrence Cap Toe Boot (Men)

$295.00
(5)
Free Delivery
Product Image
Price Matched

Mephisto Edlef Slip-On (Men)

$299.00
(83)
Free Delivery
Product Image

Florsheim Cardineli Cap Toe Derby (Men)

$99.95
(10)
Free Delivery
Product Image

Blundstone Footwear Heritage Chelsea Boot (Men)

$339.95
Free Delivery
Product Image

R.M. Williams Comfort RM Chelsea Boot (Men)

$495.00
Free Delivery
Product Image

ECCO Calcan Venetian Loafer (Men)

$179.95
(3)
Free Delivery
Product Image

ECCO Vitrus I Wingtip (Men)

$249.95
(7)
Free Delivery
Product Image

Rockport Total Motion Advance Derby (Men)

$164.95
Free Delivery
Product Image

Florsheim Tux Cap Toe Oxford (Men)

$114.95
(6)
Free Delivery
Product Image

Florsheim Postino Venetian Loafer (Men)

$104.95
(1)
Free Delivery
Product Image

Cole Haan American Classics Gramercy Wingtip (Men)

$300.00
(1)
Free Delivery
Product Image

Rockport 'Essential Details' Chukka Boot (Men)

Was:$119.95
Now:$109.958% off
(1)
Free Delivery
Product Image

Børn Brompton Loafer (Men)

$89.95
(9)
Free Delivery
Product Image

ECCO Biarritz Cap Toe Derby (Men)

$119.95
(3)
Free Delivery
Product Image

Blondo Kai Waterproof Chelsea Boot (Men)

$149.95
(3)
Free Delivery
Product Image
New!

Blondo Kai Waterproof Chelsea Boot (Men)

$149.95
(3)
Free Delivery
Product Image

Blundstone Footwear 150th Anniversary Chelsea Boot (Unisex)

$204.95
Free Delivery
Product Image

Cole Haan Jefferson 2.0 Grand Cap Toe Derby (Men)

$300.00
(4)
Free Delivery
Product Image

ECCO Holton Apron Toe Derby (Men)

$189.95
(25)
Free Delivery
Product Image

Trask Lawrence Cap Toe Boot (Men)

$295.00
(5)
Free Delivery
Product Image

R.M. Williams Comfort Turnout Chelsea Boot (Men)

$495.00
Free Delivery
Product Image

ECCO Melbourne Penny Loafer (Men)

Was:$159.95 – $160.00
Now:$109.9931% off
(8)
Free Delivery
Product Image

Florsheim Salerno Wingtip (Men)

$114.95
(27)
Free Delivery
Product Image

ECCO Calcan Venetian Loafer (Men)

$179.95
(3)
Free Delivery
Product Image

Florsheim 'Midtown' Zip Boot (Men)

$124.95
(51)
Free Delivery
Product Image

Clarks® Un.Sheridan Go Loafer (Men)

$160.00
(32)
Free Delivery
Product Image

Blundstone Footwear Chelsea Boot (Unisex)

$194.95
(5)
Free Delivery
Product Image

Rockport Marshall Buck Shoe (Men)

Was:$119.95
Now:$75.0037% off
(8)
Free Delivery
Product Image

ECCO Calcan Apron Toe Derby (Men)

Was:$179.95
Now:$84.9753% off
(8)
Free Delivery
Product Image

Florsheim Imperial Palermo Double Monk Strap Shoe (Men)

$175.00
(1)
Free Delivery
Product Image

Rockport Dustyn Waterproof Wingtip (Men)

$115.00
(2)
Free Delivery
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