You can dress comfortably. You can dress well. You can do both at the same time. But if you dress to show others who you are, remember that what you really are will show through.

On the other hand, I would not want to show up at a wedding wearing blue jeans (unless it was that kind of a wedding.)

Clothing is a thin mask. When I was a teenager, you had to wear certain things to be respected, like dirty blue jeans, long hair, "Bad Company" tee shirt, etc. Even rebellion has its conformity.