shaken, not stirred... (thanks to jamie)
being short doesn't make a person more masculine or feminine. right now i live and am trying to settle in an area where short seems to be the norm. my brother who stand those full 6' tall sticks more out than the guys who can't even reach up to 5'. i'm almost 5'3", and often meet guys who are the same height as or even shorter than me. some of them might look good in a dress, but many of them would look simply ridiculous trying to wear female clothing just because they're small.
ativan pretty much summed up how to dress masculine. only men with the perfect triangular shape, broad shoulders and narrow hips, can get away with tucking their shirt. men's wear is to be worn until it starts falling apart. pants tend to do that a little faster for me since they aren't really made for my thighs (but i've finally learned how to use a sewing machine, so i'm not planning to waste money on clothes quite yet). regular t-shirts, the almost perfectly square things, are great for hiding the waist. hiding breasts is a little more difficult, often requires a binder. but even with a binder it's hard to hide a large chest, and then it's great to hide at least the difference between chest and waist size.
i myself have ended up compromising a little. there's no point in me trying to be ambiguous about my gender, since everybody here have known me as a girl for most of my life, so instead i just wear clothes that make me feel good, without worrying about passing. i don't need to pass as a guy or be treated 100% as one, just not look too feminine all the time. if you saw my latest pic in the you look alright thread, that's a men's t-shirt, bought a faab at a very regular men's store. nobody even blinked at me trying that and other shirts on. that's how i look in it wearing a bra, you can't see how big my chest actually is in it, because it's cut straight. it would be even more difficult if it were a little looser around my chest.