Comfort is definitely #1. I try to layer myself if possible, so I don't look as small as I really am. I'm only 5'6" and very skinny. I'll have tshirt and either a hoodie, flanel or plaid shirt on top. If it's summer or just warm out I just roll up the sleeves of the plaid shirts to my elbow, but once again, mainly so I don't look so skinny. It's also very convenient to have on because even though it could be burning up outside, once you step inside that air conditioned building at 50 degrees you just roll them down and your fine while everyone else is complaining about who had their hot flashes and turned up the AC. As for "style" I buy what's cheapest, often going to the salvation army or Walmart because frankly, clothes aren't worth that $100 "designer"(ha) tag, and generally that means it's plain with no special design.
No piercings, no tatooes, and no jewelry. Just not me.
I wear a beanie right now when I'm outside, mainly cause I have a military cut and my head is freezing if I don't. Normally I don't wear a hat though. Thier uncomfortable when it's warm. If it's bright out I have some shades.