They are judged, but I disagree on the "as severely" part. A woman showing masculine cues is considered "edgy", as evidenced by the various "man-tailored" fashions that crop up periodically. You seldom see "woman-tailored" looks for men. Levi's tried marketing close-fitting "ex-girlfriend jeans" but they were unsuccessful. Here's a clip of the Ellen Degeneris show where she not only ridicules a man wearing the jeans ("take those off so you can have more kids"), but afterwards takes stabs at males wearing panties and dresses. Ms. Degeneris should know better, but being a accepted "masculine L" does not seem to give her very much empathy for those who are "feminine Ts."
There's a third camp (though the camps don't have distinct boundaries). There are those who wish to dress in feminine fashion but who don't present as female, stereotyped as the "bearded guy in a dress." Philosophically, I feel empathy for them and think that if they were accepted it would be better for everyone. Despite this, I still get a sense that, by so drastically flaunting societal norms, they are not really helping overall acceptance because they are too far from the norm to be accepted and, by association, it causes the rest of us to be misunderstood.