I wonder if that would even be called cross-dressing. I don't think anyone would think in such terms anymore. I suppose though, that some high schools would make a big issue out of girls wearing trousers to school?
There is yet another ACLU case building in Californistan right now against a (private) high school dress code, whereupon the 'enlightened' (spoiled / idle / trustafarian) students swapped clothes for a day - guys wore dresses, girls came in drab (dressed as a boy) to 'protest' the overly suppressive dress code against men with long hair. Ahhh, what the 90210 crowd will do next in the name of 'equality'...
That said, there is a woman in my office that I'm 95% sure is a Lesbian. She's very butch, and openly wears men's clothes - I know because I check out the button patterns on both her trousers (and it's always, always trousers), and shirts. She also wears mens shoes - typically sneakers, but even dress shoes - and is never seen wearing make-up. Her hair, while actually beyond-shoulder length (once or twice she's let it down, a shock to behold), is always up in a severe bun, which further effects a masculine look. I like her, great sense of humor, and very good at her job, just not my type not that it matters.
I just find it interesting that females can "get away" with such open cross dressing but that a male who would choose to don, say, a skirt and heels would be ostracized and probably forced out of the work place because it would make others "uncomfortable."