My shoulders are a little on the broad side relative to the rest of me, by standard women's proportions (though the rack o' doom comes into play when not binding, too), so to fit, stuff generally *looks* too big and baggy on me. Unless it's really stretchy stuff, which is usually tight so accentuates body parts that I don't usually feel like sharing with the rest of the world unless they're going to take them off my hands entirely.
If I bind, and can find big enough boys stuff, tops fit better. But then there's the hips, which one doesn't generally find that size on a boy my height! Ran into this problem with a jacket I found the other day - shoulders fit, chest fit, sleeves the right length and not too baggy...yet real tight around the hips when I do it up. Cargo pants are fine, at least, t-shirts and hoodies have no particular gender, but I would like more options in the fashion department than what'll get me read as a 15 year old skater...
My dad is not a whole lot taller than me, and not that much bigger build, though he can fit in smaller things by virtue of not having the chest and the hips. He has no problems running off with *my* stuff, like dress shirts and shoes, and of course t-shirts and socks (haven't found him in my pants yet, but they're nearly all women's, and it's usually only the light colored laundry loads that sometimes get mixed), but it doesn't work quite so well if I try and swipe his stuff. What's up with *that* one???
And hey, what *are* guys legs supposed to look like in jeans, anyways? The only guys in jeans I tend to see IRL are hipsters in skinny jeans, those that wear them six sizes too big with the crotch around the knees, and dad-at-work jeans, which for all I know are the male equivalent of "mom jeans".