Originally Posted by impolyt_one
I'm 28 now and have come along financially to the point where I can buy what I want, but I think if I had the foresight at 17 to get more dedicated to my style, I may have locked in my personal style long ago and be in a totally different place from where I am now. Maybe a good thing, probably not a bad thing.
I do think you should have 2 basic looks - casual and formal. You won't ever wear the latter much, but in high school, until the end, and at some points in college, I did go to enough stuff where being dressed up was required and you really don't want to be that asshole wearing sneakers with khakis and a buttonup shirt as your 'formal' look. Go black, look clean for this kind of stuff. If you can, get a proper suit, a good shirt, a simple tie, and a good pair of shoes. Girls will like it. You can choose to multi-task some of that stuff, but if it were me, I wouldn't. I'd just keep 'nice clothes' nice and leave them be. Have a nice pair of clean laceup shoes you only wear on those occasions, and they'll last several years. If you try to mix them in with casual stuff, they'll get beat up, obviously.
As for casual, it's gonna be your look 90% of the time, so do as you may. I don't raelly believe in khakis, but jeans are staple. Basic white tees. A nice pair of sneakers. Maybe a black leather jacket if you can afford it, if not, a peacoat and then some sort of windbreaker, like a Harrington. A couple v neck sweaters. A couple buttondown shirts. Keep it all trim fitting, cropped, sag your pants a bit, and enjoy being young. Do something with your hair, as well.
This is good advice.