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.

“Do you prefer ‘fashion victim’ or ‘ensembly challenged’?”

Trick question! Neither term applies to the looks in this list.

Honorable mention: we don’t see either Cher or Dee’s outfits in full during the freeway scene, but this knitted skullcap is delightful.

 

This scene is actually one of the key reasons I’ve never learned to drive.

And an honorable mention to Miss Geist also, because she’s Miss Geist.

If this scene didn’t tug on your heartstrings then you’re a terrible person.

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.

34. And huh, here’s post-makeover Tai’s style ruined in turn by Josh’s blind dive into a laundry basket.

Payback’s a bitch like that.

This is the face Tai makes when you try to argue her makeover wasn’t really an improvement.

33. Oh look, here’s another uninspiring shift dress with a high, high-waisted bow detail.

(Mainly this photo is here because of Cher’s slight case of derpface.)

32. Here’s some amazing workout wear, for example.

31. Except, oh wait, here’s some even more amazing workout wear.

Clueless, the gymspiration gift that keeps on giving.

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.

Also, yes, her chunky crucifix would be filled with cocaine.

29. Cher certainly loves a good sheer blouse. The seductive power of layering, that’s what it is.

Also worthy of note: Tai’s shiny silver Doc Marten’s. Nice touch.

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.

Thrice the awk. Enjoy!

 

27. So let’s all make an effort and be happy for Tai, this once. Even though her shoes are horrid.

26. Leopard print!

(Paired with hot pink, just like it should be.)

25. Comfy pajamas!

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.

21. Here’s some more fluff, which I think Cher actually has craftily stuck onto an otherwise bland knitted cardigan.

That’s upcycling for you.

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.

And look how everyone is clearly in their mid-20s. It’s a treat!

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.

15. Oh yes, it’s time for the Alaia. He is, after all, a “totally important designer.”

Also important: ostrich feather collars.

I think we all feel Cher’s pain in this moment.

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.

Does that sort of tip qualify as a Pinterest hack? I hope so!

13. The Kim Kardashian couch meme: Dionne did it first (though, sensibly, in a rave-worthy blouse.)

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.

And this is the face Cher makes when you try to tell her this look is only #12 on the list. Sorry sorry, but it had to happen this way.

11. But an even better sight to behold lies within: Dee’s take on church hat couture.

10. Clueless, in fact, features a number of stunning hats. Like these.

(Those plastic floral boating hats were a big thing in the ’90s, remember.)

9. And these, perhaps the pinnacle of hats.

Also note Dee’s fluffy mohair knit, not that you could miss those garish stripes really.

8. But, in fact, all of the best Clueless looks come courtesy of one Amber Mariens.

Don’t hate, ladies, celebrate.

Amber’s wardrobe hits all the flashy heights a late ’90s drag queen masquerading as a high school senior’s aesthetic should.

7. Even when she’s “borrowing” ideas from Cher, she’s doing so with style.

6. Her commitment to any given outfit’s theme is highly commendable. Don’t you want to ask her for a packet of peanuts?

5. And even when part of a large, stylish group, her oh-so-chic accessories stand out.

4.
 

Now, you see, these are reading glasses. Reading is fundamental. (So fundamental you get this GIF x3.)

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.)

2. In fact, all weddings should come with this sort of dress code.

1. Pure sartorial perfection, wrapped up in ostrich feathers and a crystal choker.

Don’t agree that Amber wins this Clueless wardrobe battle?

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