22 February 2016: There sure is a lot of cross-dressing this season
Must be a pretty low-level Japanophile to get tricked this easily.
For whatever reason, there seems to be an inordinate number of shows airing winter 2016 featuring cross-dressing of some kind. Most of the instances are gags, so it's probably just a coincidence rather than an indication of some sort of inclusionary movement or the revival of a fetish. Meaning, I don't think the "trap" fad from 2006-ish is necessarily back. But whatever the reason, there are at least six shows this season featuring cross-dressing characters, and those are just the confirmed examples I can name. Possibly there are more I either forgot or don't know about.
Yakumo would probably be less convincing as a woman without all that makeup.
Shōwa Genroku Rakugo Shinjū features a man dressing up in women's clothes, but it's for theater. It still counts, but this is part of the reason why I think the prevalence this season is more coincidence than it is an indication of some sort of trend.
Stride and Sometimes Shogi and Sometimes Drag Club.
One of the runners in Prince of Stride: Alternative occasionally gets forced to model women's clothes for unconvincing reasons. Prince of Stride also has a boy who looks like he could be the daughter of that Dangan Ronpa bear thing, but that's a different story altogether.
For crying out loud, all he did was put on a wig.
Potato-kun in Saijaku Muhai no Bahamut disguises himself as a girl for reasons that could only seem sensible in an anime. It still basically manages to trick everyone except the girl who keeps making out with him.
Iori's brother didn't really think this plan of his all the way through.
Iori's brother in Oji-san to Marshmallow disguises himself as a woman in an effort to seduce a befuddled man away from his sister. Naturally, Marshmallows are involved.
Second place is first loser, Natsuki.
Nijiiro Days (Rainbow Days) features a cross-dressing contest during a school festival. I don't know what Natsuki is crying about. He's got nobody to blame but himself.
I don't know why you'd need a disguise if nobody knows
or cares what you normally look like to begin with.
I haven't confirmed this one (although readers of the manga could probably tell you), but I'm pretty sure the bat girl in Dimension W is actually a boy. Unless Loser has multiple kids who never work together, I'm pretty sure the three assistants we've seen so far in the past seven episodes are all the same person. Since the boy wasn't in public view, and blonde bat girl is confirmed to be a disguise, there's a chance blonde bat girl is the boy's disguise. There's also the brown-haired girl, who could be a separate person, or the blonde bat girl's true appearance, or possibly the boy in disguise, but I don't actually know yet. However, Dimension W does have confirmed cross-dressing unrelated to this example. The Japanophile boy from Africa who buys traditional Japanese clothes in episode six gets tricked into wearing a woman's garment pretty much only because the two shop girls helping him thought it would be amusing.
So anyway, that's six different shows from the winter 2016 season featuring cross-dressing of some kind, and those are just the ones I know about. I've almost certainly overlooked or forgotten some obvious example.
