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Just get running shoes/ sneakers in a solid color like white, tan, or black. That’ll go with everything and you’ll be comfy. White sneakers like converse and AF1s will be too flat for you
I have the On Cloud Novas in all white and those are super comfy. I’ve found that in soles are game changer when it comes to comfort. My doctor recommended Don Joy in soles.
Second insoles. First get the insoles that work for you with correct arch and support, then find shoes that can work with them. I sometimes need to size up depending on the shoe styles
Soles insoles work well for me, have used them on a lot of hiking trips. No PF pain even with 15-20 mile days.