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Sara Pezzini has evidently decided to go undercover as a naughty Catholic schoolgirl at Dragon*Con 2007. Arguments over pop star empowerment have tipped in Spears’ favor, and she’s now more often portrayed as an icon of strong womanhood (she leaned into this on “Work B***h,” her 2013 power anthem about laboring diligently for success).

SEXY+SCHOOLGIRLS photos on Flickr | Flickr SEXY+SCHOOLGIRLS photos on Flickr | Flickr

Of course, as I'm only seen from behind, that ain't saying much, but my weight is about the same as it was in my teen years (yay! We all love a high school drama, but on film and TV the school uniform can be a surprisingly important blank canvas for a director to showcase the individual tastes and motivations of each character – especially as those wearing them are often undergoing seismic personal change. But what takes the film’s dark romance to the next level are the ethereal white gowns of lace and muslin that the girls all wear – ostensibly to offer protection from the harsh Australian heat, but also to add a touch of something ghostly about their presence right from the get-go.And, 'cause I know there are some people out there who will mind that I am a Tgirl / crossdresser / transvestite / TV / CD / gurl / tgurl / transgendered / pervert / kinkster / sissy / wow-we-have-a-lot-of-names-for-a-marginalized-group, and will be offended by knowing I have a penis that you cannot see in any of my pics/videos, I just wanna say: 'C'mon, you wanted to see a lil' school girl being spanked, so just pretend that's what I am, and enjoy it. My friend is having a fancy dress party for their 40th this weekend, I wonder if I would get away with showing up wearing this as my costume? Clueless might have celebrated its 25th anniversary last year, but the looks donned by the privileged, fashion-obsessed high school students at the centre of Amy Heckerling’s spin on Emma – here set at a monied Los Angeles high school – have truly stood the test of time (and, of course, remain a much-loved Halloween option for BFF trios around the world).

Best On-Screen School Uniforms Of All Time, Ranked The Best On-Screen School Uniforms Of All Time, Ranked

Alternatively, it’s an opportunity to subvert the sense of youthful obsequiousness we associate with them; some of cinema’s most violent villainesses will happily catch you off-guard with a pleated plaid skirt. In an interview last year with costume designer Mona May, Vogue’s Sarah Spellings got the scoop on everything from the 60-plus outfits created for Alicia Silverstone – “we really wanted to do the plaid because it was the quintessential schoolgirl outfit,” May said – to the school’s gym kit – “it’s a uniform, but [taken] to another level”. Are they pawns of some celebrity-industrial complex, exploited by nefarious forces to appeal to our basest instincts? After Japan is plunged into a recession that sees dramatic rises in juvenile delinquency, a busload of students are shipped to a remote island to fight to the death, both as an example to the nation’s youth and as a form of horrifying entertainment.

Their riffs on the uniform of their wealthy Catholic school play into their various character archetypes: Gellar’s louche-living Kathryn Merteuil unbuttons her shirt just a bit lower than Reese Witherspoon’s uptight Annette, for example. The trio of girls – all named Heather, of course, and who begin to meet untimely ends after Ryder enters their inner circle – serve as a perfect reflection of the superficial excess found in the corners of 1980s culture that the film skewers.

schoolgirl photos on Flickr | Flickr transvestite schoolgirl photos on Flickr | Flickr

So when it came to telling the story of Max Fischer (Jason Schwartzman), an intellectually snobby busybody at a posh private school who could easily have been irritating to the point of unwatchability, Anderson’s take on the school uniform made his protagonist strangely endearing.This picture briefly shot up to 63 on Explore, which is, I think, the highest any of my pictures has ever reached. Her shimmering midriff again took center stage when she wore a silky bralette in the video for her 2001 single “I’m a Slave 4 U. From Lily Cole in topknots and a tie, to an unrecognisable Paloma Faith as the resident goth with ripped tights and badges all over her pleated skirt, being bad has never looked so good.