I think, wear what you want and what you feel comfortable in, although when I put on some weight and I put my jeans on and they are tight, I don't feel comfortable in them so it makes me wonder if that 16 stone woman with the crop top on, really is comfortable, Perhaps this is about body confidence..
I see women bigger in size to me wearing an outfit I wouldn't have the nerve to wear as i would feel self conscious in it and they look great in it and seem confident, so power to them if they are happy.
In regards the fashion of guys wearing their jeans half way down their arse with their boxers or tighty whiteys showing, It makes me cringe!!! It doesn't look "cool", "hip" or "ghetto" you just look like an idiot who can't dress himself properly!