I'm new here and have recently gone sly. I can relate to your hesitation, its a big step.
I would imagine that its tough to be losing your hair when you're twenty one. but, the way i see it, you have a choice between being the guy that is a nervous wreck about whether or not his hair is jacked or you can be the dude who is confident and concentrated on the task at hand (chatting up chicks). honestly women dig confidence way more than a fancy hair cut.
what's the worst thing that would come out of going sly? you wear a hat for a week. it'll grow back super fast and if you hate it then you know never to go down that road again.
also, a bad ass beard helps.
good luck, brother