Most Comfortable Dress Shoes Men

Shop Most Comfortable Dress Shoes Men

Sponsored

$129.99

$155.00

Most Comfortable Dress Shoes, Ergonomic Design, Premium Arch Support, Men's Dress Shoes | Orthofeet Orthotic Shoes, Moreno, 9.5 / Extra Wide / Black

Orthofeet

16% off

$129.99

$155.00

Most Comfortable Dress Shoes, Ergonomic Design, Premium Arch Support, Men's Dress Shoes | Orthofeet Orthotic Shoes, Moreno, 9.5 / Extra Wide / Black

Orthofeet

$139.94

$300.00

Cole Haan Men's 2.Zerøgrand Laser Wingtip Oxfords - Brown Size Medium 10.5

Cole Haan

53% off

$139.94

$300.00

Cole Haan Men's 2.Zerøgrand Laser Wingtip Oxfords - Brown Size Medium 10.5

Cole Haan

$104.99

Cole Haan Mens 2.Zerogrand Laser Wingtip Oxford

Amazon.com

Free shipping

$104.99

Cole Haan Mens 2.Zerogrand Laser Wingtip Oxford

Amazon.com

$129.99

$155.00

Best Shoes For Foot Pain, Most Comfortable Dress Shoes For Men, Premium Arch Support | Orthofeet Orthopedic Men's Shoes, Moreno, 8 / Wide / Brown

Orthofeet

16% off

$129.99

$155.00

Best Shoes For Foot Pain, Most Comfortable Dress Shoes For Men, Premium Arch Support | Orthofeet Orthopedic Men's Shoes, Moreno, 8 / Wide / Brown

Orthofeet

$89.95

Rockport Men's Stlye Leader 2 Apron Toe Oxford Black 9 Wide

Amazon.com

Free shipping

$89.95

Rockport Men's Stlye Leader 2 Apron Toe Oxford Black 9 Wide

Amazon.com

$159.95

Cole Haan Mens 2.Zerogrand Laser Wingtip Oxford

Amazon.com

Free shipping

$159.95

Cole Haan Mens 2.Zerogrand Laser Wingtip Oxford

Amazon.com

$84.38

Rockport Men's Dressports 2 Go Plain Toe Oxford New Caramel 9.5 Wide

Amazon.com

Free shipping

$84.38

Rockport Men's Dressports 2 Go Plain Toe Oxford New Caramel 9.5 Wide

Amazon.com

$129.77

Cole Haan Men's Lenox Hill Split Toe Oxford British Tan 10

Amazon.com

Free shipping

$129.77

Cole Haan Men's Lenox Hill Split Toe Oxford British Tan 10

Amazon.com

$115.00

Skechers Men's Hands Free Slip-Ins Mark Nason: Casual Glide Cell - Duncan Shoes | Size 8.0 | Cognac | Leather/Textile/Synthetic

Skechers USA

20% Off*

$115.00

Skechers Men's Hands Free Slip-Ins Mark Nason: Casual Glide Cell - Duncan Shoes | Size 8.0 | Cognac | Leather/Textile/Synthetic

Skechers USA

$79.95

Rockport Men's Charles Road Plain Toe Oxford Black 11.5 Wide

Amazon.com

Free shipping

$79.95

Rockport Men's Charles Road Plain Toe Oxford Black 11.5 Wide

Amazon.com

$89.03

Florsheim Men's, Milano Loafer

Amazon.com

894

Free shipping

$89.03

Florsheim Men's, Milano Loafer

Amazon.com

$119.06

Florsheim Men's Medfield Wing Tip Oxford Dress Shoe

Amazon.com

Free shipping

$119.06

Florsheim Men's Medfield Wing Tip Oxford Dress Shoe

Amazon.com

$125.00

Skechers Men's Hands Free Slip-Ins Mark Nason: Casual Glide Cell Shoes | Size 8.0 | Brown | Leather/Synthetic/Textile

Skechers USA

20% Off*

$125.00

Skechers Men's Hands Free Slip-Ins Mark Nason: Casual Glide Cell Shoes | Size 8.0 | Brown | Leather/Synthetic/Textile

Skechers USA

$141.98

ECCO Men's Helsinki 2.0 Apron Toe Slip-On Loafer Black 7-7.5

Amazon.com

Free shipping

$141.98

ECCO Men's Helsinki 2.0 Apron Toe Slip-On Loafer Black 7-7.5

Amazon.com

$72.25

$85.00

Cole Haan Grand+ Men's Leather Oxford Shoes, Size: 7.5, British

Kohl's

Free shipping

15% off

$72.25

$85.00

Cole Haan Grand+ Men's Leather Oxford Shoes, Size: 7.5, British

Kohl's

$125.00

Florsheim Men's Medfield Plain Toe Oxford Dress Shoe Black 10.5 Wide

Amazon.com

2K+

Free shipping

$125.00

Florsheim Men's Medfield Plain Toe Oxford Dress Shoe Black 10.5 Wide

Amazon.com

$72.25

$85.00

Cole Haan Grand+ Men's Leather Oxford Shoes, Size: 11, Black

Kohl's

Free shipping

15% off

$72.25

$85.00

Cole Haan Grand+ Men's Leather Oxford Shoes, Size: 11, Black

Kohl's

$64.99

$100.00

JCPenney

15K+

35% off

$64.99

$100.00

JCPenney

$85.00

Skechers Men's Relaxed Fit: Harper - Forde Loafer Shoes | Size 10.5 | Black | Leather/Synthetic/Textile

Skechers USA

In store

20% Off*

$85.00

Skechers Men's Relaxed Fit: Harper - Forde Loafer Shoes | Size 10.5 | Black | Leather/Synthetic/Textile

Skechers USA

$90.00

Skechers Men's Hands Free Slip-Ins Relaxed Fit: Caswell - Frantone Loafer Shoes | Size 14.0 | Black | Leather/Synthetic/Textile

Skechers USA

20% Off*

$90.00

Skechers Men's Hands Free Slip-Ins Relaxed Fit: Caswell - Frantone Loafer Shoes | Size 14.0 | Black | Leather/Synthetic/Textile

Skechers USA

$64.99

$100.00

Clarks Mens Burchill Oxford Shoes | Brown | Regular 13 | Shoes Oxford Shoes | Comfort

JCPenney

35% off

$64.99

$100.00

Clarks Mens Burchill Oxford Shoes | Brown | Regular 13 | Shoes Oxford Shoes | Comfort

JCPenney

$64.99

$100.00

Clarks Mens Brantin Plain Oxford Shoes | Brown | Regular 8 1/2 | Shoes Oxford Shoes | Comfort

JCPenney

35% off

$64.99

$100.00

Clarks Mens Brantin Plain Oxford Shoes | Brown | Regular 8 1/2 | Shoes Oxford Shoes | Comfort

JCPenney

$76.50

$90.00

Cole Haan Grand+ Wingtip Men's Leather Oxford Shoes, Size: 8, British Ivory

Kohl's

Free shipping

15% off

$76.50

$90.00

Cole Haan Grand+ Wingtip Men's Leather Oxford Shoes, Size: 8, British Ivory

Kohl's

$64.99

$100.00

JCPenney

17K+

35% off

$64.99

$100.00

JCPenney

$64.99

$100.00

Clarks Mens Brantin Plain Oxford Shoes | Black | Regular 11 | Shoes Oxford Shoes | Comfort

JCPenney

35% off

$64.99

$100.00

Clarks Mens Brantin Plain Oxford Shoes | Black | Regular 11 | Shoes Oxford Shoes | Comfort

JCPenney

$65.00

Deer Stags Walkmaster Men's Oxford Shoes, Size: 11 Wide, Black

Kohl's

Free shipping

$65.00

Deer Stags Walkmaster Men's Oxford Shoes, Size: 11 Wide, Black

Kohl's

$59.99

$90.00

Clarks Mens Bradley Plain Oxford Shoes | Brown | Regular 8 | Shoes Oxford Shoes | Comfort

JCPenney

In store

Curbside

$59.99

$90.00

Clarks Mens Bradley Plain Oxford Shoes | Brown | Regular 8 | Shoes Oxford Shoes | Comfort

JCPenney

$160.00

Cole Haan Men's 2.ZERØGRAND Leather Laser Cut Wingtip Work Oxfords, Mens, 11, British Tan/Black/Ivory

Dillard's

3K+

$160.00

Cole Haan Men's 2.ZERØGRAND Leather Laser Cut Wingtip Work Oxfords, Mens, 11, British Tan/Black/Ivory

Dillard's

$80.00

$100.00

Clarks® Eastford Low Men's Leather Shoes, Size: 8.5, Light Brown

Kohl's

Free shipping

20% off

$80.00

$100.00

Clarks® Eastford Low Men's Leather Shoes, Size: 8.5, Light Brown

Kohl's

$56.25

$75.00

Deer Stags Mens Walkmaster Lace-Up Oxford Shoes | Black | Regular 10 1/2 | Shoes Oxford Shoes

JCPenney

25% off

$56.25

$75.00

Deer Stags Mens Walkmaster Lace-Up Oxford Shoes | Black | Regular 10 1/2 | Shoes Oxford Shoes

JCPenney

$64.99

$84.99

Dr. Scholl's Men's Sync Oxford Shoes (Dark Brown Faux Leather) - Size 9.0 m

Famous Footwear

23% off

$64.99

$84.99

Dr. Scholl's Men's Sync Oxford Shoes (Dark Brown Faux Leather) - Size 9.0 m

Famous Footwear

$56.25

$75.00

JCPenney

In store

Curbside

$56.25

$75.00

JCPenney

$64.99

$100.00

Clarks Mens Eastridge Low Oxford Shoes | Brown | Regular 10 1/2 | Shoes Oxford Shoes | Comfort

JCPenney

35% off

$64.99

$100.00

Clarks Mens Eastridge Low Oxford Shoes | Brown | Regular 10 1/2 | Shoes Oxford Shoes | Comfort

JCPenney

$129.99

Xero Shoes - Barefoot Shoes - Glenn - Men (Style: Brown, Men's Size: 7) - Zero Drop Shoes

XeroShoes

$129.99

Xero Shoes - Barefoot Shoes - Glenn - Men (Style: Brown, Men's Size: 7) - Zero Drop Shoes

XeroShoes

$90.00

Skechers Men's Hands Free Slip-Ins: Garza - Gervin Slip-On Shoes | Size 11.0 | Brown | Textile/Leather

Skechers USA

In store

20% Off*

$90.00

Skechers Men's Hands Free Slip-Ins: Garza - Gervin Slip-On Shoes | Size 11.0 | Brown | Textile/Leather

Skechers USA

$71.25

$95.00

Clarks Mens Tilden Free Slip-On Shoe | Brown | Regular 11 1/2 | Shoes Slip-On Shoes | Comfort

JCPenney

5K+

25% off

$71.25

$95.00

Clarks Mens Tilden Free Slip-On Shoe | Brown | Regular 11 1/2 | Shoes Slip-On Shoes | Comfort

JCPenney

See less

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Most Comfortable Mens Dress Shoes, Cushioned, MARATOWN - MARATOWN®
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D'MARGE
8 Most Comfortable Dress Shoes For Men

Shop Most Comfortable Dress Shoes Men
Sponsored
$119.06
Florsheim Men's Medfield Wing Tip Oxford Dress Shoe
Amazon.com
Free shipping
$119.06
Florsheim Men's Medfield Wing Tip Oxford Dress Shoe
Amazon.com
Free shipping
$125.00
Skechers Men's Hands Free Slip-Ins Mark Nason: Casual Glide Cell Shoes | Size 8.0 | Brown | Leather/Synthetic/Textile
Skechers USA
20% Off*
✕
Skechers USA
Take 5% off 1 item, 20% off 2, and 25% off 3+ items
Expires in 1 day · Enter code at checkout
Shop
$125.00
Skechers Men's Hands Free Slip-Ins Mark Nason: Casual Glide Cell Shoes | Size 8.0 | Brown | Leather/Synthetic/Textile
Skechers USA
20% Off*
✕
Skechers USA
Take 5% off 1 item, 20% off 2, and 25% off 3+ items
Expires in 1 day · Enter code at checkout
Shop
$141.98
ECCO Men's Helsinki 2.0 Apron Toe Slip-On Loafer Black 7-7.5
Amazon.com
Free shipping
$141.98
ECCO Men's Helsinki 2.0 Apron Toe Slip-On Loafer Black 7-7.5
Amazon.com
Free shipping
$72.25
$85.00
Cole Haan Grand+ Men's Leather Oxford Shoes, Size: 7.5, British
Kohl's
Free shipping
15% off
$72.25
$85.00
Cole Haan Grand+ Men's Leather Oxford Shoes, Size: 7.5, British
Kohl's
Free shipping
$125.00
Florsheim Men's Medfield Plain Toe Oxford Dress Shoe Black 10.5 Wide
Amazon.com
2K+
Free shipping
$125.00
Florsheim Men's Medfield Plain Toe Oxford Dress Shoe Black 10.5 Wide
Amazon.com
2K+
$72.25
$85.00
Cole Haan Grand+ Men's Leather Oxford Shoes, Size: 11, Black
Kohl's
Free shipping
15% off
$72.25
$85.00
Cole Haan Grand+ Men's Leather Oxford Shoes, Size: 11, Black
Kohl's
Free shipping
$64.99
$100.00
Clarks® Tilden Mens Leather Cap-Toe Dress Shoes | Brown | Regular 8 1/2 | Shoes Oxford Shoes | Lightweight|Comfort|Breathable|Cushioned
JCPenney
15K+
35% off
$64.99
$100.00
Clarks® Tilden Mens Leather Cap-Toe Dress Shoes | Brown | Regular 8 1/2 | Shoes Oxford Shoes | Lightweight|Comfort|Breathable|Cushioned
JCPenney
15K+
$85.00
Skechers Men's Relaxed Fit: Harper - Forde Loafer Shoes | Size 10.5 | Black | Leather/Synthetic/Textile
Skechers USA
In store
20% Off*
✕
Skechers USA
Take 5% off 1 item, 20% off 2, and 25% off 3+ items
Expires in 1 day · Enter code at checkout
Shop
$85.00
Skechers Men's Relaxed Fit: Harper - Forde Loafer Shoes | Size 10.5 | Black | Leather/Synthetic/Textile
Skechers USA
20% Off*
✕
Skechers USA
Take 5% off 1 item, 20% off 2, and 25% off 3+ items
Expires in 1 day · Enter code at checkout
Shop
$90.00
Skechers Men's Hands Free Slip-Ins Relaxed Fit: Caswell - Frantone Loafer Shoes | Size 14.0 | Black | Leather/Synthetic/Textile
Skechers USA
20% Off*
✕
Skechers USA
Take 5% off 1 item, 20% off 2, and 25% off 3+ items
Expires in 1 day · Enter code at checkout
Shop
$90.00
Skechers Men's Hands Free Slip-Ins Relaxed Fit: Caswell - Frantone Loafer Shoes | Size 14.0 | Black | Leather/Synthetic/Textile
Skechers USA
20% Off*
✕
Skechers USA
Take 5% off 1 item, 20% off 2, and 25% off 3+ items
Expires in 1 day · Enter code at checkout
Shop
$64.99
$100.00
Clarks Mens Burchill Oxford Shoes | Brown | Regular 13 | Shoes Oxford Shoes | Comfort
JCPenney
37
35% off
$64.99
$100.00
Clarks Mens Burchill Oxford Shoes | Brown | Regular 13 | Shoes Oxford Shoes | Comfort
JCPenney
37
$64.99
$100.00
Clarks Mens Brantin Plain Oxford Shoes | Brown | Regular 8 1/2 | Shoes Oxford Shoes | Comfort
JCPenney
35% off
$64.99
$100.00
Clarks Mens Brantin Plain Oxford Shoes | Brown | Regular 8 1/2 | Shoes Oxford Shoes | Comfort
JCPenney
$76.50
$90.00
Cole Haan Grand+ Wingtip Men's Leather Oxford Shoes, Size: 8, British Ivory
Kohl's
Free shipping
15% off
$76.50
$90.00
Cole Haan Grand+ Wingtip Men's Leather Oxford Shoes, Size: 8, British Ivory
Kohl's
Free shipping
$64.99
$100.00
Clarks® Tilden Mens Leather Cap-Toe Dress Shoes | Black | Regular 10 | Shoes Oxford Shoes | Breathable|Cushioned|Comfort|Lightweight
JCPenney
17K+
35% off
$64.99
$100.00
Clarks® Tilden Mens Leather Cap-Toe Dress Shoes | Black | Regular 10 | Shoes Oxford Shoes | Breathable|Cushioned|Comfort|Lightweight
JCPenney
17K+
$64.99
$100.00
Clarks Mens Brantin Plain Oxford Shoes | Black | Regular 11 | Shoes Oxford Shoes | Comfort
JCPenney
35% off
$64.99
$100.00
Clarks Mens Brantin Plain Oxford Shoes | Black | Regular 11 | Shoes Oxford Shoes | Comfort
JCPenney
$65.00
Deer Stags Walkmaster Men's Oxford Shoes, Size: 11 Wide, Black
Kohl's
Free shipping
$65.00
Deer Stags Walkmaster Men's Oxford Shoes, Size: 11 Wide, Black
Kohl's
Free shipping
$59.99
$90.00
Clarks Mens Bradley Plain Oxford Shoes | Brown | Regular 8 | Shoes Oxford Shoes | Comfort
JCPenney
In store
4
Curbside
$59.99
$90.00
Clarks Mens Bradley Plain Oxford Shoes | Brown | Regular 8 | Shoes Oxford Shoes | Comfort
JCPenney
4
$160.00
Cole Haan Men's 2.ZERØGRAND Leather Laser Cut Wingtip Work Oxfords, Mens, 11, British Tan/Black/Ivory
Dillard's
3K+
$160.00
Cole Haan Men's 2.ZERØGRAND Leather Laser Cut Wingtip Work Oxfords, Mens, 11, British Tan/Black/Ivory
Dillard's
3K+
$80.00
$100.00
Clarks® Eastford Low Men's Leather Shoes, Size: 8.5, Light Brown
Kohl's
1
Free shipping
20% off
$80.00
$100.00
Clarks® Eastford Low Men's Leather Shoes, Size: 8.5, Light Brown
Kohl's
1