I've Rule 63'ed Leon from Kingdom Hearts, and as far as I can tell, I'm one of the only people to put him (her?) in shorts, as oppose to a skirt. The character just doesn't strike me as a skirt-wearing type of person. There are a couple of things I want to fix (want new shorts, and new shirt, and need to fix my arm belts).
But personally, as long a gender-bent version of a Character stays true to the character and personality of said Character, then everything is fine. It's when male-to-female versions get overly sexy that it seems like blatant attention-whoring, and when female-to-male versions seem more like a person to go on a shopping rampage at Hot Topic that I begin to have a problem. But when costumes are well thought out and well made I actually do enjoy seeing the interpretations.
"Everybody tells tales . . . it's just the dead talk more quietly than other people."