Style

The 37 Best Looks From "Clueless"

Cher Horowitz does not get the best grade in the fashion stakes, and she can't negotiate her way up either. Way harsh... but fair.

Posted on

37. Look at Cher's surprised expression. It's, like, "how did this look make it into a 'best of' list?"

Perhaps a good question, but that is a cute little rose detail. Also, there's a denim vest on display and that's not something you can really overlook.

36. A pivotal moment, the kiss scene, sure... but Cher's sneakers look positively orthopedic.

(This is basically the starter section of looks that HAVE to be acknowledged even though they're, like, kinda bland.)

35. Honestly, pre-makeover Tai's aesthetic just ruins this. She really could be a farmer in those clothes.

When the Troll Doll on your baggy t-shirt has a better dye job than you, well, then you're in a bad place.

30. Sarah Michelle Gellar did this look better in Cruel Intentions. And Kathryn Merteuil would have worn this without the white tank top, mind you.

28. In fact, let's briefly acknowledge Tai's edgy warehouse party look on its own.

She's the babysitter who snuck out on her 9-year-old charge, somehow wearing the kid's clothes, basically. But that's not necessarily a bad thing.

24. Headbands!

This sparkly Lurex sweater is almost too much — ok, it's definitely too much, and yet somehow it works paired with these check pants. It shouldn't, but it does.

23. Cher would have surely donated this fine Italian outfit to Lucy following her date night with Christian.

It's wrapped up in too many awkward memories to place high on this list. Also it probably smells of burnt sausage.

22. Anyway, it's time to start celebrate those floaty, fluffy feather moments.

Technically this pen isn't part of Cher's outfit. But here she is thinking hard about ways to incorporate the wispy ball of fluff into some sort of headband, or maybe glue it to a platform shoe.

20. Here's one Tai look that's actually coherently composed, if not necessarily outright "good."

Obviously you can't risk pissing Tai off too much, or she'll call you a virgin who can't drive. (And I've already admitted I can't drive, so it would hit close to home.)

19. Because here's Cher in a much better plaid ensemble. (And there's more plaid to come, still) . Also, here's Amber wearing a swan years before Bjork.

18. A maroon velour two piece and knee-high white socks — just wonderful. Dee is quite the stylista, which obviously isn't a real word and thus something Valley Girls would say.

Again, let's rise above comments directed at Tai's fugly shoes. (We'll discuss Amber — and her epic pigtails — further down this list, don't worry.)

17. And anyone with the cojones to wear a bright red pleather mini skirt in the daytime deserves kudos.

Just make sure that kudos isn't monetary, because that sort of well-meaning gesture could lead to your arrest for solicitation.

16. From pleather to leather: Cher paired her leather mini with another sheer blouse.

Fun fact:: I found this look so alluring as an 10-year-old watching the movie for the first time that I briefly considered I might be heterosexual after all. But then I realized I just wanted to be able to pull off such an outfit myself, and went back to dressing up in my Mom's old clothes.

14. Recreate this look for yourself by spraying whipped cream out of a can down your shirt. It'll only last for a minute, but then you have a good excuse to eat the whipped cream.

12. Perhaps the most iconic pair of Clueless outfits, this carefully coordinated explosion of plaid is a sight to behold. Definitely one of the movie's best wardrobe moments.

We all hope Dee and Cher planned their outfits not only to match, but to match each other's.

3. Amber's take on boot camp chic: camo colors with furry cuffs and collars. Obviously.

(And, look, there's Cher behind her in a knit sweater straight out of a Banana Republic outlet store. It must be said, there's no comparison.)