Just gotta chime back in --
Desmo April -- I DID have enough confidence to wear leather pants in my 20s. But it just wasn't my style. (Although I suppose, even if it had been my style, I wouldn't have been able to wear them anyway, because I didn't have the money!)
I have the confidence now, too. The issue for me is not confidence. I've never been a particularly conservative dresser, either. I've always had a dark and gamine edge (except that one stretch in my late 20s where I experimented with colourful surf wear, and it never really worked). It's -- as Una says -- about authenticity.
When I said, 'who gets to wear leather pants', of course I was being tongue-in-cheek. I anticipated the chorus of 'ME! Nobody can tell me what to wear! I dress to please myself!' -- and of course that's true. We all have to dress in a way that pleases us. So if Suz, who is not an actual rock star (although she wrote an award-winning book, which makes her a kind of literary rock star, right?) suddenly decides that she's going to dress like Debbie Harry, then you go girl.
The catch is not caring what people think. If you truly don't, then you get to wear anything -- including black leather rock n roll pants, neon hot pants or a pair of spangled heart-shaped sunglasses. But I do care about my audience -- at least to some degree -- and it's not due to a lack of confidence. For me, the whole point of fashion and style is being able to project an image of yourself to the world that you feel reflects who you are on the inside. When we talk about dressing for 'self-expression', isn't that what we mean? Otherwise we're just playing dress-up.
That obviously isn't everyone's opinion, though.
And it is fun to experiment with clothes a bit, because otherwise, how would your style evolve? It's important to always move forward, while at the same time staying true to who you are.