All in the question but yeah.
In high school would you think someone who wore a dress shirt (untucked) or collared shirt with a loosened tie has style. Or is that guy a complete tool?
Most Helpful Girl
As long as you're confident with what you're wearing - you can pull anything off.
I can seriously say, unless you're dressing extra freakish, no one is going to care in the future what you wore in high school.
Going to my 10 year HS reunion I couldn't even recall who wore what and why in high school. So wear what you want while you still can - you have an opportunity to express yourself at will, enjoy it.