Well, the pink shirt is quite "feminine", in my opinion, and in a deleted scene we see her bed filled with plushies, and she is also wearing a purple shirt, which again is quite "girly"; so, while i can see her being kind of a tomboy and her father calling her Jude the dude for that, I don't think she wouldn't wear dresses.



I don't either agree or disagree on the second one, that depends on how the writers handle Judy, since we never saw her teenage years and maybe it's true that she has never dated (I personally think she probably has, to be honest). Anyway, I don't see what that has to do with her nit wearing dresses.



I honestly think that dresses fall into the "sexy" or "elegant" category, especially the one I've put her in, but that it's probably subjective, so...



In the end, I think that being a strong woman doesn't just mean wearing only pants, that would be reductive and maybe a bit offensove for the women, so I think Judy would be completely fine with dresses.