You know, when I was 22 it didn't matter what I wore, I looked ok. I could even wear a pair of Speedo swim trunks and not offend. Many years later, I can only look ok if I am careful about the attire. Something about expando-gut, drooping muscles, and sagging tuchus. So I would argue that clothing aesthetics are highly relative.

When we go on rides together, the wife makes me wear looser MTB shorts. When I ride on my own, I say the heck with it and become an COMIL. (Clueless Old Man in Spandex).