I ran across one I hadn't thought of in years.
I don't know how it has aged, I'd imagine not well. In critics eyes I'm sure it would be blasted.
But
Just One of the Guys (1985) is a pretty ambitious flick, especially for 1985. This gal thinks that all the good jobs go to guys, so she dresses up like a guy and goes to high school. There have been other movies that took a similar type movies since, but they were far more Disney-fied.
This movie is pretty upfront about the struggles between women and men, dudes getting bullied for femine features, and of course, romance dynamics and so on and so forth.
These days, it would be crucified by the LGBTQWOEVBNOUIBNW community and would probably never get made, frankly, but this is an interesting look into gender differences.
But the real reason I remember it...
NSFW
https://giant.gfycat.com/AcrobaticFemaleChuckwalla.webm
Those made quite an impression when I was a kid.