Category #6: Fashion Sense
Both these guys can rock a suit like no one’s business, but that’s not what we’re looking at here. The question is which of these guys is a better casual dresser on their day off? How do they look like in ‘normal people clothes’, if you will.
When he’s actually wearing clothes, Bilzerian mostly keeps it generic in plain white/black T-shirts, probably the most expensive plain T-shirts money can buy, but still. Also often rocking cargo shorts and dope jackets – definitely a cool customer:
Leo on the other hand can dress like an absolute tramp and still be dripping swag all over the shop. Just look at him in this picture. The guy’s wearing white socks with Vans, his beard looks like shit, he’s kind of taking giant awkward steps but somehow he’s still the swaggiest guy on the street. Bilzerian might be rocking the better clothes, but Leo can pull off average joe clothes like no one else. It’s a tough one – I think this has got to be our first draw of the competition.