
I personally like it, but in my opinion, you should wear what you like, thinks suits you well, and what you're most comfortable with and not what he or others would like! If you wanna try it and see what happens, that's fair, but ultimately, it should be about what you enjoy wearing most. And the right person is gonna like you for you and not what you wear!
Wearing leggings probably won’t get that much of a reaction, but he would probably still like them. If I see a woman wearing leggings when I don’t normally see them wear leggings, I usually just think, “oh she’s wearing leggings.” I don’t know a lot of guys who have a strong opinion either way but most guys like them.