The reason you have this weird affection toward fluffy-tipped pens and Mary Janes, jarring plaid and Pam Anderson pimp hats, baby tees, cropped tops and Jeeps with the top off, white collared shirts and knee high socks, The Mighty, Mighty Bosstones, Egg McMuffins, Marvin the Martian and boys named Josh is all because of Clueless.
For so many of us it was the first window into the world of fashion. It was the first time we saw just how transformative, expressive and actually fun clothing could be. Remember that Sex & the City didn’t air until three years later and even then you likely weren’t allowed to watch it.
(But because this movie was based off of Jane Austen’s Emma your strict mom who was concerned about feminist values and the effects that movies can have on young, soft brains decided that this one — with its sexually active teenagers who argued their way to better grades and confused soda pop for drugs made from crack rocks — was okay. Choose your battles.)
We spent our most formative years re-watching and absorbing Cher & co’s mid-90s lexicon — Calvin Klein, “as if,” Alaïa — and we didn’t even have to know what any of it meant. Those words seared themselves into our brains just as wonderfully and deeply as her pre-iOS outfit-selecting closet, and they stuck.
I mean thank god, right? Because if you don’t spend your adult life in search of an excuse to dress like the well-manicured cast of Clueless, then what do you do with your days?
In honor of the movie’s anniversary, we made up an excuse called Dress Like a Clueless Character to Work Day. You should try it. Your boss will understand — bet you your very first designer bag that she, too, still does the ocean hand motion any time she hears Coolio’s “Rollin’ With My Homies.”
Photographed by Krista Anna Lewis.