Cole Haan Men's Hawthorne Plain Oxford Shoes
$111.99$139.99Comfortable Dress Shoes — February 2026
Curated selection of Comfortable Dress Shoes pulled from our shop in February 2026. Explore listings, transparent pricing, and merchant details in one place.
Allen Edmonds Fifth Avenue Cap-toe Oxford Dress Shoe
$295.20$369.00
Men's Amberjack The Original
$156.00$195.00
Allen Edmonds Men's Park Avenue Cap Toe Oxford
$360.00$450.00
Men's amberjack The Cap-Toe Obsidian
$159.20$199.00
Thursday Boot Company Men's Lincoln Suede Loafer
$144.00$180.00
Allen Edmonds St. John's Double Monk Strap Dress Shoe
$340.00$425.00
Thursday Boot Company Men's Saint Double Monk Leather
$144.00$180.00
Stacy Adams Men's Karson Wingtip Double Monk Strap Dress Shoes
$104.00$130.00
Naturalizer Jayla Slingback Pump Shoes, Silver Leather, 6.5 Wide | Block Heels, Strap
$112.00$140.00
Stacy Adams Men's Sync
$100.00$125.00
Tory Burch Women's Cap-Toe Leather Pumps with Bow Detail
$260.00$325.00
Red Wing Men's Weekender Oxford Shoes
$207.99$259.99
amberjack shoes World's Most Comfortable Obsidian Dress Shoe
$156.00$195.00
Dr. Comfort Jackie Women's Mary Jane Dress Shoe
$112.20$140.25
Sofft Women's Casandra Block Heel Loafers
$107.96$134.95
Wolf & Shepherd Men's Crossover Derby Shoes
$220.00$275.00
Beckett Simonon Men's Dean Oxfords
$191.20$239.00
Born Men's Lance Lace-Up Leather Oxfords
$104.00$130.00
Free delivery by Fri
$200.00$250.00
Cole Haan Men's Original Grand Cityspectre Cap Toe Oxfords
$119.96$149.95
Magnanni Segovia Cap Toe Oxford
$420.00$525.00
J.Crew Men's Essex Leather Derbys
$360.00$450.00
Ecco Men's Metropole London Derby
$156.00$195.00
Wolf and Shepherd Crossover Longwing WS-F19-SJ02
$110.40$138.00
Amberjack Men's Cap-Toe Wide Shoes
$159.20$199.00
Allen Edmonds Park Avenue Cap-Toe Leather Oxford Dress Shoe
$303.98$379.98
Dr Comfort Stallion Men's
$112.20$140.25
Amberjack Men's Hybrid
$180.00$225.00
Allen Edmonds Men's Fifth Avenue Cap-Toe Oxfords with Dainite Sole
$319.20$399.00