Not Ensembly Challenged: Still-Wearable Clueless Fashion

If you want to know how teens dressed in the 90s, just watch Clueless. Sort of. Not the main characters – nobody really dressed like that. No, next time, keep your eye on the background players. The unflattering jeans, the scrunchies, the awkwardly cut shirts – those were the true Kids In America, 1995.

Because Cher, Dionne, and friends were basically cartoons of the most extreme mid-90s teen style, most of their clothes would look ridiculous today. Heck, most of them looked ridiculous in ’95. That was kind of the point. But now that the 90s have circled back into fashion there are some looks that would look just as fresh today as they did 20 years ago. Wear these, and you will not have to choose between identifying as fashion victim or ensembly challenged.

Cher’s Pajamas

I can’t find a better shot of them, but I want these fresh-as-a-daisy crop top pajamas right now.

Cher’s Grade Change Outfit

The perfect simple, preppy, tennis-y outfit. Not that Cher played tennis.

Tai’s Post-Makeover, Picture-In-Elton’s Locker Outfit

There’s a lot of plaid in Clueless. Much of it unwearable. But this – this is adorable, and honestly very typical of 90s teens. (Source: when Clueless came out I was 8 and lived with the next-coolest thing to a unicorn for an 8-year-old girl – a teenage sister who sometimes let me hang out when her friends were over). Not so wearable: Ambular’s … outfit… thing.

Dionne’s Multicolored Extensions

Between Stacey Dash’s general agelessness and the popularity of colorful yarn braids, it’s hard to believe that this isn’t 2015. Seriously, how amazing does she look?

The Alaia

Along with the yellow plaid outfit, this is Cher’s iconic look (thanks for nothing, Iggy Azalea, haven’t you done enough?). The wacky feather-trimmed jacked should probably stay at a val party in 1995 where it belongs, though.

Dionne’s Layered Necklaces

If you look closely, Dionne has these layered gold necklaces – a cross and some kind of pendant – that she wears in a few scenes. Very 2K15 appropriate.

Cher’s Post- Hall/Geist Setup Celebration Outfit

I know I said that there’s a lot of plaid, and, well, there IS a lot of plaid. But this is the cutest outfit and brings together so many of the mid 90s looks I remember: the 70s minidress revival, prep (knee socks!), plaid, and unnecessary hats.

Cher’s Gym Class Outfit

I could never wear the tank top over a tee without looking like a Sister Wife, but this puts all the stupid, schlubby t-shirts and sweats I wore to gym class to shame. See also: an early prototype of the cell phone case. Amber, stop.

Cher And Dionne’s Outfits When Tai Is Wearing Farmer Clothes

Empire waists were a big deal – even for kids. ONe of my school concert outfits had a bow just like Cher’s and I thought I was so cool. Sportswear was also a big deal, a la Dionne’s amazing black and hot pink ensemble. And Tai… well, Tai. Troll dolls were in, what can I say. Also the girl in the background is wearing a shirt with this weird-shaped flower that was for some reason ubiquitous.

Cher’s Dress. Says who? Calvin Klein.

Another 90s trend, though you may not believe it from this movie: minimalism. A lot of plain tank tops, Gap staples, basic scoop-necked wedding gowns – a subdued reaction to the wackiness that was the late 80s and early 90s. This dress is perfectly on-trend and still looks lovely, especially without that sheer thing she drapes over it.

Cher’s Emma-Inspired Shopping Dress

This dress! There’s the minimalism and empire waist we talked about before. Is the waistline a nod to the Jane Austen era since Clueless is loosely based on Emma?

Dionne’s Wedding Hair

Before the flower crown, there was the flower everywhere. Why do I bet that if you walked into Claire’s or The Icing, 90% of the stock is the same as it was when I was 8 and Clueless was king?


5 thoughts on “Not Ensembly Challenged: Still-Wearable Clueless Fashion

  1. Pingback: Extreme Makeover: Clueless Edition | cookies + sangria

  2. I just found your blog and I love it and I might be even more obsessed with Clueless b/c the red dress she’s wearing there in that photo was for her date with Christian, and I don’t know the designer but it wasn’t the one she referred to as the Azzedine Alaïa, which she wore with “the wacky feather-trimmed jacket” when she, Dionne and Tai made a cameo at the Val Party.


    • Great comment! You’re totally right, the “a-what-a” is similar but has thicker straps than the one she wears on the date and is more satin-y. Now to find a good photo – all of them seem to be from the waist up in gross val party smoke.


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