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I have slightly longer than shoulder length hair and sometimes I like to wear a baseball cap outdoors. It may seem like a silly question, but what is the best way to wear your hair with a cap? I don't want to look dorky or feminine. Should I wear it in a ponytail or loose, pulled through the back or not?
Always keeping in mind that the wearing of almost any kind of hat will make your head sweat by trapping close all of that body-heat, and that sweat is bad for both your present growth and the teeny glands that produce the hair . . .
I have a friend who's hair length is about the same as yours and also likes to wear baseball caps. He ties all of his hair up, puts the cap on and anything that is sticking out he just tucks in so you can't tell that he is a long hair.
In response to leafcatcher, he wears one of those "trucker" baseball hats like the one's they give you in little league with the mesh in the back so it doesn't trap as much heat...
I usually just pull the hair back into a tail either at the ear level or just above and pull the tail through the opening in the back of the cap. Doesn't look either dorky or feminine.
-J