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1990’s Photos Straight Out Of ‘Clueless’

This is Cher's guilty pleasure list of outfits.

By Micaela Montaña

Published 3 months ago in Feels

Ugh, as if! The ‘90s were a whole mood: part fashion show, part fever dream, and all attitude. While Clueless may have been the queen bee of plaid skirts and teen drama, it was really just the tip of the frosted-lipstick iceberg.


These photos? They look like they were ripped straight from Cher Horowitz’s photo album… if she took a detour through your local mall, a school dance, and a Delia’s catalog. Crimped hair, interesting fashion, and more denim than a Levi’s warehouse… it’s peak 1990s fabulousness with a side of fashion crimes.


Warning: nostalgia ahead, and it's wearing platforms.

  • 1

    Roll Up, Roll Up. Dress ‘Em All!

    Cher’s room isn’t a disaster: it’s a fashion exhibit. Clothes everywhere, drama pending.

    Roll Up, Roll Up. Dress ‘Em All!

  • 2

    As If We’re Not Lost, We’re Just Adventuring

    Goofy, grungy, and full of wilderness energy. Pretty sure Cher would’ve said, “You’re totally foraging.”

    As If We’re Not Lost, We’re Just Adventuring

  • 3

    Parking Lot Paparazzi Vibes

    This group outside of school? Practicing their best Cher smirks for monogrammed selfies.

    Parking Lot Paparazzi Vibes

  • 4

    ‘Do You Even Lift, Or Just Accessorize?’ Fashion Edition

    One’s got the ‘I meticulously picked this for irony’ look, the other’s rocking a mustache like it’s a mood enhancer.

    ‘Do You Even Lift, Or Just Accessorize?’ Fashion Edition

  • 5

    Ctrl + Alt + Cher It’s on

    Typing up gossip, or just dodging the real world. Either way, computers never looked so ambient.

    Ctrl + Alt + Cher It’s on

  • 6

    As If I’m Not Rad Enough

    Locker-boarder aesthetic: totally 90s, totally in your face and totally Clueless-approved.

    As If I’m Not Rad Enough

  • 7

    Three’s Company, Cher Style

    Friendship goals? Skirts, long hair, and cheekbones that refused to quit.

    Three’s Company, Cher Style

  • 8

    Sugar Crash? More Like Fashion Crash.

    Candy-stalling: sweet, sticky, and dripping in iconic tween chic.

    Sugar Crash? More Like Fashion Crash.

  • 9

    Green, Baggy, and Ridiculously On-Point

    Baggy’s not sloppy, it’s a statement. Cher would’ve scoffed and made it a trend.

    Green, Baggy, and Ridiculously On-Point

  • 10

    Rollers With Jeans That Slay

    Did someone say “Preppy renovation”? Because she’s serving volume and vintage vibes.

    Rollers With Jeans That Slay

  • 11

    Driveway Drama, Parking Lot Coolness

    This bunch by their ride is serving “just got here and I already own the place” vibes.

    Driveway Drama, Parking Lot Coolness

  • 12

    Fashion Speaks In Iconic Levels

    The fashion police is here, you better hide away those sneakers.

    Fashion Speaks In Iconic Levels

  • 13

    Our Room, Our Rules (And Romance?)

    So many posters, so much personality. This could be Cher’s secret hideout.

    Our Room, Our Rules (And Romance?)

  • 14

    Giggles Over Gossip

    Those shrieks? Probably about some scandal only Cher could invent. Totally relatable.

    Giggles Over Gossip

  • 15

    Just Kicking Time With Style

    Their hangout could double as a fashion studio. Jeans? Check. Attitude? Double check.

    Just Kicking Time With Style

  • 16

    Rooftop Realness

    They’ve skipped the hood or trunk, because elevating your cool on the roof is a Cher-approved move.

    Rooftop Realness

  • 17

    Happy Is the New Black

    Their joy is contagious and preppy. Cher would totally patent that smile as fashion.

    Happy Is the New Black

  • 18

    Room-Only Rebellion

    They’re not just crashing a casual space, they’re curating a vibe. Posters, pillows, personality.

    Room-Only Rebellion

  • 19

    An Apple a Day Keeps the Boring Away

    Snack meets class: making school feel like a Vogue editorial, one crisp bite at a time.

    An Apple a Day Keeps the Boring Away

  • 20

    Slip-On Sneakers, Slay-On Style

    Borrowed from boys, perfected for girl power. Cher would say they made brunettes her best accessory.

    Slip-On Sneakers, Slay-On Style

  • 21

    Bronco? Please. This Is Desperately Clueless.

    No matter how fake that horse is, she’s turning lunchtime into a rodeo. Yeehaw, with flair.

    Bronco? Please. This Is Desperately Clueless.

  • 22

    Fresh Air and Fresh Fits

    Books out, outfits on: these teens just strolled into the ‘90s like it was a runway.

    Fresh Air and Fresh Fits

  • 23

    Love & Loud Stares

    Their vibe? Two attitudes rubbing off on each other. Madonna would’ve called it “vogue grunge.”

    Love & Loud Stares

  • 24

    Pool Night Meets Style

    Night game, messy hair, and pool gossip: so 90s, so iconic. That glow? Not waterproof, just timeless.

    Pool Night Meets Style

  • 25

    Aqua Toned, Just Zoned

    From jeans to big t-shirts, it’s like that one Clueless fitting room; but real life, and cooler.

    Aqua Toned, Just Zoned

  • 26

    When You’re That Extra

    Let’s be real: closer to Cher’s comedic gold than actual family dinner. Props for the commitment.

    When You’re That Extra

  • 27

    Smirk & Snarl in Synth

    Raven lippies, disheveled hair: utterly undone, infinitely iconic. Cher’s pantsuits wish they were this edgy.

    Smirk & Snarl in Synth

  • 28

    Hair Today, Trends Tomorrow

    They didn’t follow trends, they invented them. Cher could’ve taken notes.

    Hair Today, Trends Tomorrow

  • 29

    Roommates & Ridiculousness

    Just two friends, one mood, endless laughter. If Cher was their BFF, this would be the vibe.

    Roommates & Ridiculousness

  • 30

    Casual & Colorful

    These teens are in the "good outfits" list.

    Casual & Colorful

Categories:

Feels Retro

Tags:

'90s 90s nostalgia nostalgic 90s 90s teens 1990's clueless
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