I wear leathers when I do highway riding: chaps, gloves, and my beat-up old Mustang leather jacket (not vintage, I've had it for 12 years). And a helmet because I hate eating bugs. In town it's frequently just jeans and a T-shirt with a bandanna to keep my hair out of my face (the irony of not wearing a helmet in high traffic flow to protect my brain but always wearing one in low traffic flow so I don't get bugs in my face is not lost on me).
When I was much younger, before I was a rider, I did the whole underground-heavy-metal guy thing with chains on my aforementioned leather jacket (which was worn every day in all weather), three wallet chains, four or five rings, 3 necklaces with swords and Maltese crosses, leather wristband on either wrist, jeans intentionally ripped...when you're 19 and looking for your little corner of the world, that's okay. You just want to feel like you're part of a group. But by the time I was 22, it just took too damn long to get ready to leave the house. I look at young guys who do this now, and just chuckle to myself.