Ok so the way my boyfriend dresses has never really bothered me until someone pointed out something to me...he wears the same exact thing all the time. Everyday he wears a FOX t shirt and khaki colored knee length shorts from American Eagle. Of course he has more than one pair of shorts and he has probably every FOX shirt under the sun so he's not literally wearing the same thing everyday. It's never bothered me...I never even noticed really but would it bother you? On the other hand, I guess I don't dress up too much either!