The idea of gendered clothing has always bothered me. Growing up, I struggled a lot with my identity due to the way these ideas were forced on me. I had a lot of issues with femininity and responded by dressing in a very "masculine" manner: cutting my hair extremely short, wearing cargo shorts, men's cut t-shirts, etc.,. I've always felt uncomfortable in dresses and heels, babydoll cut shirts, most jewelry, etc., so dressing this way allowed me to feel comfortable in my own skin. At first, some kids at school gave me crap; I remember one boy shouting at me during P.E. that I had a boy's haircut (which was sort of the point?). Other than the occasional struggle with administrators who wanted me to wear a dress instead of dress pants and shirt, it mostly faded into the background at school. It was a huge issue for my father though. He would scream at me that I needed to "act like a lady" lest anyone think his daughter was, gasp, a lesbian. He had a bizarre fascination with controlling my appearance. I've long hypothesized that he was himself a closeted homosexual and this was a form of projection, but that's not really the point. Today, I still dress a lot "like a guy." Pretty much all of my shirts are "guy's shirts". I don't wear sandals, wedges, or heels. I alternate mostly between a pair of Chucks and Vans (the latter admittedly has a cute Aloha pattern). I can wear some skater dresses, though anything that completely bares my shoulders/back is a complete no-go. I've grown my hair out to past my shoulders. I like to wear a watch with a flowery band, stretchy bands with cute designs, and some bracelets with flower shapes on them. I really like floral patterns, to be honest. Some of my pants are "girl's pants" and I never wear cargo shorts outside of my apartment. So, wearing "men's clothing" wasn't exactly a phase for me, though I do wear some "women's clothing" now. All that said, even to this day, no one would really say that what I do/did could be called "cross-dressing." Why is that? Why is it (mostly) acceptable for me to wear (Number Withheld) x 28 jeans, a non-clinging t-shirt, Chucks, and a hoodie while a man wearing a blouse, Capri pants, and any jewelry would be called a cross-dresser? What we're each doing is literally no different. It really bothers me. Now, I don't intend this to be a topic about whether cross-dressing is "funny," like in movies. I'd just like an honest discussion about why it's this way. I really hope this is the correct place for this topic (seems like it'd fall under "politics and philosophy" to me, at least). How do you all dress? Masculine, feminine, a mix? How do you feel about styles of dress being described this way? tl;dr: It's (more) socially acceptable for a woman to "dress like a man" than it is for a man to "dress like a woman." Additionally, women are rarely called "cross-dressers" in this circumstance, while men almost always are. Why is that?