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Comfortable Dress Shoes

Stop enduring hours of agony by standing and walking in a pair of dress shoes that pinch and cramp the feet. Comfortable dress shoes are available for both men and women and are a pain-free way to accessorize any formal, casual or semi-formal outfit without having to wear cringe-worthy shoes.

The definition of comfortable dress shoe will vary depending upon how comfort is measured. Whether it is a style that conforms to the foot, offers good arch support or just overall feels warm and cozy, there is a comfortable men’s or women’s shoe design just waiting to be slipped on and taken for a walk.

Loafers have long been associated as a men’s and women’s shoe style that embraces comfort. The sleek shoe sides on and the low heel provide a specific level of comfort that is now associated with one of the many comfortable dress shoes available at Macy’s.

Calvin Klein combines a classic loafer design but adds a bit of modern flare to the overall look to create a men’s shoe style that is sleek and stylish. Available in black, brown and grey, these dress shoes embrace the foot and provide the comfort loafers are notorious for providing.

For a comfortable woman’s loafer consider a pair from Sperry. Designing a number of top-sider and traditional loafers, Sperry shoes offers an ideal fashion accessory that is comfortable without compromising a woman’s wardrobe. 

If you don’t want to trade in those high heels for a flatter comfortable shoe, consider accessorizing with a women’s high-heeled boot from Vondra Boots. Vondra Boots creates a number of modern yet comfortable boot designs. Available in both flat heels and high heels, the designs from Vondra Boots provide the comfort the foot needs without having to trade in the high-heeled look.

Perfectly accessorize any casual, formal or semi-formal outfit with a pair of fashionable, comfortable shoes and aches and pains in the feet could disappear. Take a walk through Macy’s collection of men’s and women’s comfortable dress shoes to find a pair that fits your definition of comfort and perfectly accessorizes any fashion ensemble.

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    Comfortable Dress Shoes

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    • 2 colors
      Clarks Collection Women's Addiy Kara Booties, Created For Macy's
      $135.00
      Sale $119.99
      Extra 20% off code: SCORE
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      Extra 20% off code: SCORE
      With offer $95.99
      Bonus value $200
      $29.99 Diamond Earrings with any $50 purchase
      Bonus value $200
      (14)
    • 4 colors
      Born Ouvea Booties, Created for Macy's
      Black Friday Special
      $150.00
      Sale $90.00
      Bonus value $200
      $29.99 Diamond Earrings with any $50 purchase
      Bonus value $200
      (24)
    • 3 colors
      Wide Calf
      Naturalizer Dane Wide Calf Riding Boots
      Black Friday Special
      $210.00
      Sale $126.00
      Bonus value $200
      $29.99 Diamond Earrings with any $50 purchase
      Bonus value $200
      (2)
    • Extended Widths
      Clarks Women's Emslie Monet Booties
      $120.00
      Sale $99.99
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      With offer $79.99
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      $29.99 Diamond Earrings with any $50 purchase
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      (44)
    • Clarks Women's Sillian Tana Cloudsteppers Booties
      $120.00
      Sale $99.99
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      Extra 20% off code: SCORE
      With offer $79.99
      Bonus value $200
      $29.99 Diamond Earrings with any $50 purchase
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      (13)
    • 3 colors
      Clarks Collection Women's Emslie Craft Shooties
      $90.00
      Sale $79.99
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      With offer $63.99
      Bonus value $200
      $29.99 Diamond Earrings with any $50 purchase
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      (7)
    • 2 colors
      Naturalizer Kim Riding Boots
      Black Friday Special
      $199.00
      Sale $119.40
      Bonus value $200
      $29.99 Diamond Earrings with any $50 purchase
      Bonus value $200
      (1)
    • 3 colors
      Naturalizer Jessie Riding Boots
      Black Friday Special
      $160.00
      Sale $96.00
      Bonus value $200
      $29.99 Diamond Earrings with any $50 purchase
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      (5)
    • Clarks Collection Women's Emslie March Dress Boots
      $180.00
      Sale $149.99
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      With offer $119.99
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      (4)
    • 3 colors
      Wide Calf
      Naturalizer Jessie Wide Calf Riding Boots
      Black Friday Special
      $160.00
      Sale $96.00
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      Bonus value $200
      (3)
    • 7 colors
      Extended Widths
      Naturalizer Zarie Booties
      Black Friday Special
      $110.00 - 119.00
      Sale $66.00 - 71.40
      Bonus value $200
      $29.99 Diamond Earrings with any $50 purchase
      Bonus value $200
      (152)
    • 3 colors
      Born Sylvia Booties
      $135.00
      Bonus value $200
      $29.99 Diamond Earrings with any $50 purchase
      Bonus value $200
      (67)
    • 3 colors
      Born Chaval Booties
      Black Friday Special
      $145.00
      Sale $87.00
      Bonus value $200
      $29.99 Diamond Earrings with any $50 purchase
      Bonus value $200
      (60)
    • 3 colors
      Born Carmel Harness Booties, Created for Macy's
      Black Friday Special
      $135.00
      Sale $81.00
      Bonus value $200
      $29.99 Diamond Earrings with any $50 purchase
      Bonus value $200
      (13)
    • 2 colors
      Born Carmel Booties, Created for Macy's
      Black Friday Special
      $135.00
      Sale $81.00
      Bonus value $200
      $29.99 Diamond Earrings with any $50 purchase
      Bonus value $200
      (5)
    • 3 colors
      Wide Calf
      Naturalizer Kelsey Wide Calf Riding Boots
      Black Friday Special
      $210.00
      Sale $126.00
      Bonus value $200
      $29.99 Diamond Earrings with any $50 purchase
      Bonus value $200
      (4)
    • 4 colors
      Extended Widths
      Naturalizer Blair Booties
      Black Friday Special
      $140.00
      Sale $84.00
      Bonus value $200
      $29.99 Diamond Earrings with any $50 purchase
      Bonus value $200
      (21)
    • 2 colors
      Clarks Collection Women's Merana Amber Booties
      $130.00
      Sale $109.99
      Extra 20% off code: SCORE
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      Extra 20% off code: SCORE
      With offer $87.99
      Bonus value $200
      $29.99 Diamond Earrings with any $50 purchase
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      (11)
    • 3 colors
      Naturalizer Dane Riding Boots
      Black Friday Special
      $210.00
      Sale $126.00
      Bonus value $200
      $29.99 Diamond Earrings with any $50 purchase
      Bonus value $200
      (3)
    • 11 colors
      Extended Widths
      Aerosoles Silver Star Pumps
      $79.00 - 89.00
      Now $69.99 - 89.00
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      Extra 20% off code: SCORE select colors
      Bonus value $200
      $29.99 Diamond Earrings with any $50 purchase
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      (18)
    • 2 colors
      Born Cook Riding Boots
      $240.00
      Bonus value $200
      $29.99 Diamond Earrings with any $50 purchase
      Bonus value $200
      (35)
    • Clarks Collection Women's Hope Track Booties
      $140.00
      Sale $119.99
      Extra 20% off code: SCORE
      Extra 20% off select merchandise!
      Extra 20% off code: SCORE
      With offer $95.99
      Bonus value $200
      $29.99 Diamond Earrings with any $50 purchase
      Bonus value $200
      (2)