I get my hair cut at a place where it costs $45 and I get a haircut every 1-2 months at best.

I wear my shoes until they break. I wear Vans Sk8 old skool high tops most of the time.

I am also on track to retire by 40 if all goes well. (Which is to say I don’t have THAT much money)

Maybe hthe GP is confident enough to have passed by the shallow indicator of displaying their wealth? The richest people I know personally (and who I deeply respect) absolutely delight in people under-estimating them, assuming they're "poor plebs" like the rest of us. They like money, recognize it's important and appreciate what it allows, but feel no need to advertise it.

I mean, people who say "why would I want status symbols" tend to not purchase designer clothes and $500 hair cuts. Because those are status symbols.

But bags as shoes is impractical. You want a sole to protect your feet.