Comfortable Shoes for Men Over 50

After 50, a shoe has to do two jobs: look sharp and feel good from morning to evening. These loafers, slip-ons and casual shoes were picked for cushioned or padded insoles, soft linings and flexible soles, and many slip on without laces.

For long days on your feet, choose a cushioned sneaker or a padded loafer. For dinners and events, a soft leather loafer gives you the polish of a dress shoe with far more comfort. Suede and soft leather mold to the shape of your foot as you wear them.

Looking for bigger sizes? See men's shoes in size 13 & 14. Every order ships free with tracking, and you have our 30-day money-back guarantee.

Questions we often get

What makes a shoe comfortable for all-day wear?

A cushioned insole, a flexible sole, a soft lining and enough room at the toes. Every pair here has at least one of these, and most have several.

Are slip-ons good for older men?

Yes. They go on and off without bending to tie laces, and a good slip-on still looks smart with chinos or tailored trousers.

What shoes should I wear with chinos?

Loafers and clean leather sneakers are the easiest match; suede loafers for a more relaxed look.