Crossplay is exactly what you think it might be, cosplay that involves crossdressing. It's not the same as gender-bending an existing character, as Gender Bent Justice League did this year at San Diego Comic-Con. With crossplay, a female fan will present herself as a male character and vice versa.
Ultimately, crossplay is no different from cosplay, it's a fan-oriented art form that can take many different paths. Some people don't make a major effort to conceal their actual gender. Others take painstaking measures to resemble the opposite-gender character as closely as possible. The choice is up to the fan.
While you may stumble upon crossplayers at any event that encourages costume, the phenomenon is most common within the anime fandom. Sure, we may see a few girls portraying male characters from The Venture Bros. at San Diego Comic-Con, but nothing draws the sheer amount and diversity of crossplayers like anime conventions. In Southern California, we tend to see the most crossplayers at Anime Expo and Anime Los Angeles.The obvious reason for this is that there are simply more cosplayers at anime conventions. You might see a lot of costumed photos in photo galleries from San Diego Comic-Con, Long Beach Comic Con and other similar comic book events, but that's not the majority of the crowd. At conventions like Anime Expo, if you aren't in costume, the assumptions are frequently either that you're a newbie, you're there for work or you're there to keep an eye on your kids.
Whether you're a woman intending on appearing male or a man planning to appear female, there are some preparations you'll have to make for a convincing crossplay.
For women, a big part of this involves binding your breasts to appear flat-chested.
"It's very common," says Romy Meyerson, who was crossplaying as Izaya Orihara from Durarara!! when we met her at Anime Expo. "It can be easy, you can use a sports bra and an ACE bandage, or it can be complex as getting a compression shirt."
For men, stuffing a bra may be a relatively simple task, but trying to mask facial hair is a much more time-consuming.
"I had to research mustache concealer," says Bryce Masunaga, who was dressed as Fate Testarossa from Magical Girl Lyrical Nanoha at Anime Expo.
More often then not, when we see male crossplayers, they're dressed as characters who wear skirts. The art of crossplay, though, becomes trickier if you're taking on a character who wears a skintight outfit, like Celty Sturluson from Durarara!! (and we have seen at least one Celty crossplayer). Tucking is the best-known option for temporarily concealing the bulge, and, if you read the tutorials, you'll gather that it's not that easy.