Do you have any evidence of gender roles so specific and enforced so strictly that "pretty much everyone" gets "screwed over" for not matching up with them exactly in "every possible regard?"
How do you account for all the people, perhaps a majority, who don't seem to have any problem with traditional gender roles, but in fact, embrace them? They don't seem to feel they are being "screwed over."
I don't expect you to agree with me, of course, but just try one on for work one day. You'll be amazed.
But to be honest, I feel a little silly making a big deal about the ability to wear a skirt or have a purse for instance.
It's called a messenger bag. Usually cheaper, more versatile, and a leather one can last you a lifetime.