From time to time I wear womens clothes since I'm super short and i have a tiny chest with child bearing hips so for example women's dress shirts fit me perfectly and don't look baggy like men's shirts of the same neck size. I also like t-shirts where they just use the exact same T-shirt for both male and female. In my opinion as long as you are skinny, cute and slightly androgynous then you can pretty much wear anything as long as you don't end up looking like a tranny.