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Chris Sacca
He definitely has a one-of-a-kind look!
Well now that the other comment has me thinking of Shark Tank, I’m going to with Kevin O’Leary. He’s showing off his brain with his fashionable do.
Easily Richard Perry, billionaire hedge fund guy bought Barney's so he dresses down in more street style with super trendy avant-garde designers
Ehh idk if someone can say all time because the fashion choices of the 80s look so fucking tacky right now but at the time it was considered best dress and in the future this will happen when 2040 analysts want to puke when they see deal sleds and patagucci that people wear now.
Batman
Robert Smith
Michael Burry
Ken Fisher
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