These Preppy ‘Clueless’-Inspired Pieces Never Go Out of Style — Shop Plaid, Polos and More

It’s been 30 years since Clueless hit theaters. Yes, 30! And somehow, the prep-meets-playful style still holds up. If you watched it in real time (or owned the VHS), chances are you’re not dressing for homeroom anymore, but that doesn’t mean you can’t pull off the look thanks to these updated Amazon finds.

With the milestone anniversary happening this month, we’ve got Clueless-core on the brain. To get the style, we’re reaching for pleated minis, tailored tweeds, tennis-inspired sets and sleek sweater vests that channel Alicia Silverstone‘s Cher and Stacey Dash‘s Dionne in a modern, grown-up way. You don’t need fuzzy pens or knee socks (unless you want them), but a little structure, polish and prep? That’s still very much in style. Keep scrolling to shop 13 preppy, Clueless-inspired pieces that feel as chic as they were in 1995.

These Preppy ‘Clueless’-Inspired Pieces Will Never Go Out of Style

1.  Closet Staple: This Clueless-core plaid mini dress has thin straps and a flattering shape that makes it easy to layer with a tee or jacket.

2. Cher-Approved: This pleated mini skirt looks nearly identical to the one Cher wore, but if yellow is not your thing, there are nine other colors to choose from.

3. Throwback Friday: This button-down mini dress brings just the right amount of throwback energy. Add oval sunglasses and you’re ready for the weekend.

4. Shopping ‘Fit: This matching two-piece set feels like something you’d throw on to shop in Melrose. It’s easy, coordinated and looks put-together without trying too hard.

5. Power Suit: Business casual gets a preppy update with this cropped blazer and pleated skirt combo. Add tights and boots for a polished look.

6. Varsity Layers: Throwing a vest over an Oxford shirt with a mini skirt is still the formula for a photo-worthy outfit. Shoppers say they always get compliments when they wear this look.

7. Pretty Polished: This curve-hugging combo is perfect for tea around town.

8. Court to Café Set: This neutral two-piece set looks like something you’d wear to tennis practice . . . and to grab lattes right after. 

9. Modern Coded: Tweed and plaid go together like Dionne and a flip phone. This blazer and skirt set gives the classic texture a modern twist.

10. Red Slip Revival: As Cher once said, “Sometimes you have to show a little skin.” This simple slip dress channels that same energy — it’s subtle, sleek and sexy.

11. Argyle Essential Vest: This stretchy, sleeveless sweater vest works well with jeans, skirts or trousers. 

12. French Touch Beret: This beret is the easiest way to make your outfit feel Parisian stylish. Pair the hat with a trench or an oversized blazer, and you’re good to go.

13. Prep School Socks: These tall knit socks are cozy enough for cold days come fall. They’re so cute when they peek out of boots or when paired with a mini skirt.