I answered this question http://www.girlsaskguys.com/fashion-style/q1409267-i-need-girls-opinions-about-a-guy-wearing-girls-jeans earlier and inspired me to post this question for fun
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I think it depends a bit. I'm generally very, very easy going with gender identity stuff. I don't like those stuck-up gender roles. I myself have quite a lot of girl in my gender identity and I openly admit that. However, many things just wouldn't fit me I believe. I also can't think of a lot of "typical girly" clothes. And of course it also depends what you're gonna consider typical male or female. For example in many countries of the world, having long hair is considered absolutely inappropriate for a guy. However, in my country Switzerland, as well as in the US, it's no problem. Also, my conservative uncle from Spain told his son (my cousin) that he would kill him if he would ever dare to wear an earring. Southern Europeans can still be very weird about that kinda stuff. Earrings are considered girly and gayish. However, in Switzerland and in the US, people hardly pay attention to guys wearing earrings. It's almost considered unisex.
I think as a fun experiment, I would enjoy completely dressing up as girl for a day. But for every-day life, it really depends on the item. Some things I might wear but there are also some I wouldn't.1