The funny thing is if you get successful people praise you for sticking to your preference.
It's like a fuck-you card.
People will blame the college kid for not dressing more professionally.
But suddenly if the college kid becomes Zuckerberg/Jobs people will praise him.
"Oh he just always wears [that hoodie/jeans/tshirt/turtleneck]. He's cool and simple and down-to-earth like that not like all these other stupid materialistic people who buy expensive clothes."
There's nothing wrong with that, as long as you don't mind the consequences that follow.