If you try on one pair of classic, cork Birkenstocks you'll be amazed by the healing powers. I hated them with a passion until I worked retail and have never looked back. Cured my mom's shin-splints and I switch to them ASAP when my back or joints bother me because you can't believe how they adapt to your specific feet while instantly correcting your gait. I swear they're miraculous. I've aged into unflattering bare feet and even wear them with socks rather than look cool and be significantly less comfortable.

(Keep it simple--the Arizona sandal with two straps or the Boston mule/clog with an open heel. They now make lots of styles, some that try to pass for regular shoes, but I only know these two work. And you don't need a backstrap to keep the sandal on--the ridge under your small toes does this and supports your posture/gait at the same time. Step into genius-level comfort.)

Totally my shoes reflect my personality! My only chucks experience was purchased to last feet that had stopped growing and have me blisters.

I did Doc Martens in college for miles of daily walking across campus with flair and comfort; added Birkenstocks and Tevas for retail and nature hikes through gorges. I then moved up to Fluevogs for function and flair. Totally prioritized caring for the only pair of feet I will ever have and I'll spend good money on shoes that help. I'm fairly non-conformist and these all appeal to that part of my identity. You'll also never catch me waiting tables between more professional gigs without Dansko clogs popular with surgeons, chefs, and nurses.

I'll also choose a shoe shaped like a foot over a wing-tip every time. When I lived in a cold climate, I wore the heck out of contractor boots to office jobs that allowed jeans or khakis. I'll spend extra money on shoes and glasses every time. The rest of my fashion is boring and largely classic staples with a little more color than most men (used to) feel comfortable wearing, but my feet and my eyes need consistent quality that will last and keep me waking and seeing.