When i was young and hang out in skateparks, there were always some guys with dissolving shoes, crappy boards and dirty clothing that would absolutely rip the skatepark. I always wondered if i'd ever get so good that i can skate around looking like "that"… because my raw skill would carry me.
I would probably do the same as a billionaire. There would be no reason for me to look "nice" if i didn't feel like it. People would pretend that i look great anyway.