Feel comfortable That´s all that matters.

well in my point of view, I guess that each person has their own way to dress.
The important is that they feel comfortable and try to be yourself. Don´t try to imited other, be the one you are although other people judge the way you dress .

of course you must learn to dress for each ocassion, for example when you go to a wedding, to the beach , to a funeral, to the football game and to the church.