This is an interesting thread and it caught my eye because I’ve been thinking a lot about what I wear lately and what others think.
The context is I’m a guy, mid 30's, happily married, fairly good looking, in good shape, and - here it comes - I love wearing leather pants. I think they’re the best kept secret in the clothing world: they’re super comfortable, they form fit to one’s body and I don’t care what “Joey and Chandler” think, they look damned good when they’re accessorized well - if you can see past the stereotypes. But that’s the problem right there isn’t it? Those accursed, and very deeply rooted, stereotypes.
With the generally greater acceptance of alternative lifestyles, lesser degree of race issues, etc in our society [i.e. we’re far from perfect, but we have made improvements], I had this fantasy that people just might have moved beyond passing judgement based merely on an article of clothing. I also figured that if I were careful in how I wore the pants, and if I bought ones that were really high quality [Versace, Gucci], then just maybe all of the enlightened people in our wonderful society would see past the stereotyped images - even for just a moment - and think “you know...that’s not too bad”. Well...save for a very few exceptions, it sure hasn’t happened.
For a long time, my confidence to wear leather pants was bolstered by the occasional positive comment [“you look really good today”, “you pull it off well” or “you know, now that I’ve let that look settle in for a moment, you really do look good”]. Also, I loved the feeling of being unique, because all my life, I’ve been fed this lie that individuality means something and I guess I must have believed it. Sadly, I’ve come to realize that adults, young or old, have pretty much the same attitudes that they had in junior high: if you’re in any way different - any way at all - you’re an object of ridicule. Adults just hide it better and wait for you to leave rather than make fun of you to your face. That’s the only difference. For a while I didn’t care, but over time, the long, sideways looks kind of erode at the confidence.
Anyway, my point, I guess, is that if you chose to dress in anything other than what is universally accepted for each context [dockers to work, sweats or shorts on the weekend, jeans when it’s cooler outside], you WILL be judged. Expect it - it will happen. If you have the confidence to let it wash off your back, then I salute you. But don’t expect too many others to do so.