Actually it depends on where I'm wearing it. I have a few t shirts that are just now starting to look right on me, because it's taken me almost 10 years to fill them out properly. When I bought them, they were a little 20 something ( not A&F, but gay store stuff from when I lived in NYC - "club clothes") Anyway they are sort of retro 60's, but also kind of generic --- sooo I tried one on and it finally fit right and I wore to a club in New Orleans on NYE - Yeah it was tight for a guy my age, but damn there were some guys dancing naked (practically) on the bar - so who cares? And it was dark.
Otherwise, yes, I'm really careful about what I wear these days. Nothing makes me look older more than dressing too young (or too tight)