It's actually pretty basic, I would think--men's clothing pretty much consists of generic, plain clothes, such as jeans and button-up shirts over t-shirts. Women's clothing pretty much consists of men's clothing, with additional styles and cuts, such as spaghetti straps, frills, and dresses.
Although modern society has shaped our minds to believe that certain styles and looks are "wrong" on certain genders, there really isn't a good reason for it, other than one in particular; hair. Body hair. This includes facial hair, armpit hair, back hair, abdomen hair, leg hair, and--with respect to the topic--pubic hair.
You can change this question, if you'd like, to "Why can't guys shave their body hair without being judged, while girls can?"
Body hair is generally a sign of masculinity in the mind of modern society. Although people aren't generally taken aback by repulse when guys shave their body hair, women who
don't shave their hair are thought to be "ugly" and "disgusting," because they're showing of a masculine feature, despite the fact that they're women.
Now, you might think this is strange, because guys--unless they're overconfident, of course--try to cover up their body hair and shave their faces when they walk about out in the open. This is because body hair is thought to be appealing sexually--when on a man--when presented to someone at an appropriate time. When it's revealed at INappropriate times, it's seen as repulsive, as it is on a woman.
Now, to answer your question, why
can't men wear women's clothes?
-Women's clothes are designed to be revealing. A lack of body hair is considered feminine, and having body hair is considered masculine. When a masculine man wears what's designed to be a revealing dress for a woman, and their body hair is revealed, it's seen as pretty damn repulsive.
-A woman doesn't
have to be revealing if they don't want to be--since men's clothes aren't revealing, they can wear them and get away with it. They won't be, by
all but one means, as sexually attractive to men as they would be when they wear women's clothes. That remaining means is that if a woman has a lot of body hair, they may have better luck fitting in by wearing men's clothes than they would by wearing women's clothes.
-In all other situations, modern society simply isn't used to seeing men in women's clothes.
...And that's my answer.
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Why can girls dress like guys but guys cant dress like girls? 
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