Comfortable Men’s Dress Shoes

Comfortable Men’s Dress Shoes – Our Top Picks!

Our top picks in comfortable men’s dress and business shoes. Our recommendations include lace-up oxfords as well as comfort slip-ons.

All shoes are ideal for the office or business environment as well as after work entertaining and everyday wear. Each brand of shoe offers both incredible inner anatomical comfort and outer style and are available in various colors and sizes.

All recommended shoes can be purchased online with free shipping through Zappos shoes. All links will open in a new browser window.

May your work day be filled with comfort!

Free Shipping on all Men’s Dress Shoes!

Comfortable men's dress shoes by Cole Haan
Cole Haan Air Madison Wing Oxford

Elevate your style with these outstanding Cole Haan dress shoes. Built with concealed Nike Air technology soles for superior comfort. Supple calf skin leather uppers. Also available in Black and Tan, and wide sizing.
Comfortable men's dress shoes by Allen Edmonds
Allen Edmonds Park Avenue

Experience true style and luxurious comfort with this hand-stitched dress shoe from renowned men’s footwear brand Allen Edmonds. A sleek and sophisticated exterior is made with premium leather. Lightly padded footbed offers contoured support and comfort all day long. Lifetime guarantee. Also in Grey.
Comfortable men's dress shoes by Ecco
Ecco Birmingham

Elegant lace-up dress shoe needs no ornamentation other than its polished European calfskin upper. Padded footbed offers added support and all day comfort. Luxury on your feet.
Comfortable men's dress shoes by Clarks
Clarks Un.Olaf

Classic lace-up comfort oxfords. Smooth leather linings wick away moisture to keep your feet cool and dry. Padded footbed offers continuous cushioning and support for all day wear. Also in Black and wide sizes.
Men's dress shoes
Allen-Edmonds Walden

Exquisite handsewn leather penny loafer from Allen Edmonds. Full leather linings mold to your feet for all day comfort. Also in Burgundy. Wide widths available.
Men's dress shoes by Cole Haan
Cole Haan Air Madison Cap Oxford

Rich calf leather upper offers lightweight, breathable wear and immediate comfort. Unique Cole Haan footbed and outsole offers flexibility and Nike Air Technology shock absorption to protect the knees, hips, and back. Combine comfort with a prestigious and professional look to your wardrobe. Also available in Black and Burgundy.
comfortable men's dress shoes
Frye Otis Penny Loafer

Handcrafted in USA from premium leather. Full-leather lining offers breathability for a healthy environment for your feet. Leather-covered padded insole with comfort heel insert provides enhanced cushioning. Also in Brown.
Men's dress shoes
Rockport Northfield

A shoe that suits both the office and long hours in the field, walking on concrete floors or hard surfaces. The cushion sole and rugged outsole provide the ideal blend of comfort and practicality. Also in Brown and Nubuck. Wide sizing available.
Men's Dress Shoes
Mephisto Marlon

An incredibly luxurious and soft comfort dress shoe with leather uppers and inners. Lightly padded footbed offers all day comfort. These are the world’s most comfortable men’s dress shoes! Also in Black and Hazelnut. These shoes earn rave reviews for comfort.
Men's Dress shoes
Rockport Margin

Durable, comfortable, and eminently practical dress shoe. Strong but flexible construction for long wear. Leather-lined padded collar and tongue. Available in wide sizes.

Most Comfortable Men’s Dress Shoes, Most Comfortable Men’s Business Shoes
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