in theory, yes, feminine clothing could look good on a male. whether any particular article of clothing looks good on any particular being is open to debate. I mean half the time feminine clothing doesn't even look good on females. some articles of clothing aren't really appealing, and unfortunately the same goes for people. there are too many variable for such a vague question... you can't ask if something looks good without actually showing it to your audience. if you're gonna leave it up to our imaginations the "outfit" you've described would make ya look like a tranny, which isn't a great look in my opinion.

I'm sure if you were to post images it would provoke more useful responses (as well as a slew of not-so-useful responses). the original post is just going to produce a lot of indefinite answers, and people saying they don't give a fuck about what you wear.

Most clothing nowdays is unisex
I get pretty much judged for wearing pink shirts/socks etc simply because they're pink but tbh pink suits me and the girls like it so I don't really care what other guys think

I guess it's more that you shouldn't care what people think of you if you want to wear something rather than you should only want to wear something if people think good things about you for wearing it, if you know what I mean (i probably typed that out hella weird)