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I think this is largely dependent on who you hang around. Since I'm an attorney, it follows that most of my friends are attorneys, and tend to not dress like bums even on a weekend at a party to watch a game. Maybe lawyers and investment bankers are the last holdouts here?Ever since I started dressing better, my friends now call me "grandpa." And I'm only mid-40's. But, to most people below 40, if you're dressing up beyond having to for work, then they look at you strangely. And I'm talking about something as simple as chinos and an OCBD. For most of them, dressing up means putting on your nice jeans and tshirt. They ask my why I'm so dressed up all the time. I tell them I'm actually quite comfortable. And keep in mind, I'm not really that dressed up. Only in comparison to them. As much as all of us like finer clothes, the majority of the young people getting older are quite fine with very casual clothes no matter what setting they're in.
Any time I have ever received an odd comment for being dressed nicer than the usual shlub, my response is usually "hey, someone's got to bring a little class into this place". It tends to work.