Seems extremely tacky to me. It's like: "you're not a teenager skateboarder, yes you have money but you're not that cool. if you want to feel young and cool again go f 18 year olds in thailand or something"
What's the point of having fuck you money if you can't say fuck you? I'll wear what is comfy, appearances be damned.
OK, why not wear a tracksuit then? Why bother with a formalish look above the shoes? You're not quite fuck you. You're reaching.