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!

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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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Comfortable Men’s Casual Shoes

Our top picks in comfortable men’s casual shoes. Here you’ll find casual shoes chosen for their all-day support, comfort, and latest style. All shoes are available in various colors and sizes. All comfortable men’s casual shoes can be purchased online with free shipping from our recommended suppliers, Zappos and ShoeBuy. Each link will open in a new window.

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Comfortable shoes by Merrell
Keen Ontario

Ramble the world in style with this handsome, comfort lace-up from Keen. Anatomical footbed provides cushioning, support and all-day comfort. Durable rubber outsole provides great traction on all surfaces. Also in Slate Black.
camper pelotas comfortable men's casual shoes
Camper Pelotas

The original retro lace-up athletic shoe. These classic Camper Pelotas are comfort and style icons. Durable leather uppers. Removable comfort footbed. Rubber outsole with multi-nub tread for stable grip on all surfaces. Great, sophisticated walking shoes.
Comfortable men's casual shoes by Keen
Keen Austin

The classic Keen Austin will keep you feeling comfortable all day. Waterproof leather upper with top-stitched details. KEEN Patented Toe Protection. Ultra cushioning footbed cradles the natural contours of the foot for all day comfort. Available in a cool range of colors.
Comfortable men's dress shoes by Merrell
Merrell World Legend

Travel the world or walk the streets in these classic comfort slip ons. Smooth leather linings wick away moisture to keep your feet cool and dry. Cushioned anatomical footbed offers continuous support for all day wear. Sticky rubber outsole delivers great traction on all surfaces. Available in several colors.
Comfortable men's shoes by dr martens
Dr Martens 8053

Dr Marten’s started the comfort revolution with their World Famous Air-cushioned Sole. Detailed stitching. Exquisite handsewn Nappa leather. Padded ankle collar. No shoes can match these for street credibility. Also in Brown.
Men's comfortable casual shoes by keen
Ecco Sport Biom Grip

Ecco comfort, rugged design and handsome looks! Rich oil suede leather and camel leather uppers. Memory foam footbed molds to your feet making every step a cushioned one. Also available in Black.
comfortable men's dress shoes
Patagonia Loulu

A low cut lace-up shoe with comfort and sustainability built right in. Compression-molded EVA footbed provides cushioning comfort with ample support where you need it most. Dri-Lex wool footbeds and natural wool liners aid with moisture management and temperature control. Durable latex soles offer sustainable traction. Also in Light Brown.
Men's comfort casual shoes
Merrell Jungle Moc Leather

A go-to comfort shoe for errands and running around town. These Merrells suit both the weekend and/or long hours in the field, walking on concrete floors or hard surfaces. The cushioned and rugged outsole provide the ideal blend of comfort and practicality. Antimicrobial technology keeps your feet healthy and odor free.
Most Comfortable Men’s Casual Shoes
Copyright ©2005-2013 Most Comfortable Shoes

The most comfortable men’s casual shoes are often overlooked if you are unaware of the make up of a truly comfortable casual shoe. Many elements go into the manufacture of the men’s casual shoes. They usually have a wide toe box to accommodate your toes without pinching or friction. Most well-made men’s casual shoes should also have a firm heel counter, which cradles the heel, and keeps your foot in place to help control your walking posture. They should have a semi-rigid or rigid shank. The shank is the narrow part of a shoe’s sole, located beneath the foot arch. They will have a removable inner sole that can be removed to gain extra room or for the insertion of orthotics. Comfortable men’s shoes have a long vamp, which is the upper part of a shoe that covers the front part of the foot and a foam lining that molds to the foot to reduce pressure points and provide extra comfort and protection. The can have a firm compression EVA midsole and breathable upper to help control foot moisture and bacterial build up. They are often made with elasticized materials or with closures made of Velcro that can easily be made tighter or looser to accommodate for swelling in your feet. A padded collar and tongue in comfortable men’s casual shoes help protect sensitive areas of the feet, reduce irritation and secure the fit of your shoes. Comfortable men’s shoes, boots and clogs are usually constructed with the above features. This will ensure that men have an experience of ongoing all-day support.