You're right. It is strange. Nobody would say that. The first two sentences are extremely natural; the second two are unnatural. You could maybe change it to "Do I look good in it?". There's a joke/ cliche that women trying on clothes always seek assurance from their partners by asking "Does my bum/butt look big in this?". The only acceptable answer to that is "No, you look great, honey".

I think all the sentences are fine (I’m a native English (US) speaker). I disagree that no one would say “it compliments my figure.” That’s untrue. I do think it’s probably a bit formal sounding, but I hear it all the time, “that color really compliments your complexion”, stuff like that. So yes, the word compliments is frequently used in fashion and clothing.

All perfect but compliment should have been complement.