There are dress shoes that have the vibram sole, which are VERY comfortable. My suggestion would be to buy a high quality shoe that he can resole multiple times. Also, don’t be afraid to buy high quality shoes that are used (if you can find his size). Vibram makes their sole in multiple colors, including black.

A lot of people like Allen Edmonds. They’re pricey but they’ll last and you can resole them multiple times. (His size will usually be on sale or check eBay.) Also, there are boots that look like dress shoes. It can help with ankle support and helps keep the swelling down, if needed.

https://olukai.com/collections/mens-slippers I wear these working from home. Slip resistant and A+ quality. The back heel folds down for when you just need to slide them on. Worth every penny.

If you are value shopping, you can find quality brand luggage at places like Marshals, Ross, etc. Hard shell carry-ons have held up well for me and I can fit more in them.