Cher's Best Looks From Clueless

Clueless (1995) — Photo: ©Paramount/Courtesy Everett Collection

It's hard to believe that Clueless hit theaters over 25 years ago — especially since all of those fashion moments are just as relevant today as they were back in 1995. Sure, Cher Horowitz (played by Alicia Silverstone) may have been clueless when it came to love (and, well, driving), but she definitely excelled when it came to putting together an enviable outfit.

As a style salute to the film and its costume designer Mona May, as well as a way to prep for Halloween, we're looking back at some of the character's most iconic fashion moments: from her white body-hugging Calvin Klein dress to the plaid set we simply can't quit. Reminisce with us as we visit some of Clueless's best fashion moments. And if these looks leave you "totally buggin'" (in a good way), we've found a few shoppable items to help you recreate them, too.

01 of 12

Cher's "Most Capable" Outfit

Despite having turned her closet inside out looking for her most professional ensemble ("Where's my white collarless shirt from Fred Segal! It's my most capable looking outfit!"), Cher failed her road test, got into a fight with Tai, and promptly went shopping in search for solace.

Shop now: Dolls Sky Sleek Stunt Argyle Mini Skirt ($38); Everlane The Oversized Blazer ($185); Nili Lotan Tara Shirt ($172, Originally $350); Hue Soft Opaque Sock ($7); Mansur Gavriel Glove Mary Jane Flats ($233, Originally $395)

02 of 12

Her Scheming Outfit

With her beret, pinstriped jacket, and crisp button-down, Cher looks like a pro while playing match-maker to her two teachers, Mr. Hall and Miss Geist.

Shop now: ASOS DESIGN Crochet Beret ($18); Sanctuary Slit Back Tunic Blouse ($109); Ralph Lauren Pinstripe Wool Crepe Blazer ($295)

03 of 12

Cher's Famous Plaid Ensemble

Clueless - Cher's Plaid Separates — Everett Collection

With the help of her technologically advanced closet, Cher was always matched to perfection. Case in point: Her yellow plaid separates.

Shop now: Swinging Chicks Clueless Inspired Yellow Tartan Set ($320)

04 of 12

Cher's Match-Making Look

Cher wears red while playing cupid to Mr. Hall and Miss Geist. Her ploy? Offering them her dad's Italian roast coffee share, with the excuse that drinking it herself might stunt her growth. "I wanna be 5'10" like Cindy Crawford."

Shop now: Polo Ralph Lauren Classic Fit Oxford Shirt ($99); RED Valentino Tartan Mini Skirt ($995); Sunday Best Winston Cropped Sweater Vest ($68)

05 of 12

Cher's "Playing the Favorite" Look

Clueless - Playing the Favorite — Everett Collection

Cher definitely wanted to look sweet while showing her father her new-and-improved report card, and this white scrunchie, ivory cardigan set, and black skirt combo helped her achieve just that. Plus, we'd be lying if we said we didn't refer to her initial speech during various times in our lives. "Well, some teachers are trying to low-ball me, Daddy. And I know how you say, 'Never accept a first offer,' so I figure these grades are just a jumping off point to start negotiations."

Shop now: SKIMS Jacquard Scrunchie ($12); Bershka Tie Front Cardigan Twinset ($36); Los Angeles Apparel Tennis Skirt ($50)

06 of 12

Cher's Take on Goth

A sheer black top over a white tank, complete with a cross necklace and black jeans is the witchy look we're itching to recreate this fall. And yes, we'll be adding Cher's vampy lip to the mix, too!

Shop It: ASOS DESIGN Mesh Crop Fitted Shirt ($23); Zara Ribbed Top ($6); Nadri Cross Necklace ($55); Madewell 10" High-Rise Skinny Jeans ($128); Charlotte Tilbury Matte Revolution Lipstick ($34)

07 of 12

Her Date Look With Christian

Clueless - Date Look With Christian — Everett Collection

For her first date with the new guy from school, Cher selected a second-skin white mini dress, which elicited the question from her dad, "What the hell is that?" Cher informs him it's a Calvin Klein dress, then leaves to dance the night away in the sexy, statement-making look.

Shop now: SKIMS Fits Everybody Slip Dress ($62)

08 of 12

Her School Look

The focus here is on Tai, fresh from her makeover, but Cher herself is rocking a must-try preppy look, layering a sweater vest over an Oxford with a button-front mini and over-the-knee socks.

Shop It: J.Crew Relaxed-Fit End-on-End Cotton Shirt ($80); Abercrombie Slim Cropped V-Neck Sweater Vest ($55); Pilcro 90s Micro Denim Skirt ($98); Sheertex Over the Knee Socks ($59)

09 of 12

Cher's Red-Hot, Having-a-Boy-Over Dress

Clueless - Cher's Red Dress — Everett Collection

Cher has her own piece of fashion advice when it comes to boys. "Sometimes you have to show a little skin," she narrates while trying to impress Christian. "This reminds boys of being naked, and then they think of sex."

Shop now: Susana Monaco Thin Strap Mini Dress ($150)

10 of 12

Cher's Black-and-White "Workout" Outfit

Clueless - Cher's Black-and-White Workout Gear — Everett Collection

Cher wears one of her signature looks during P.E: A tank layered over a tee. However, this outfit doesn't just work for gym class. Add a pair of jeans or trousers and this not-so-simple top pairing is perfect for whatever you have planned.

Shop It: Athleta Renew Seamless Support Top ($59); Madewell Northside Vintage Tee ($16)

11 of 12

Cher's "Buns of Steel" Workout Look

Cher sports a checkered one-piece as she and Tai work out to a "Buns of Steel" video, but with the addition of a blazer, she's practically Emily Ratajkowski.

Shop It: Girlfriend Collective Moon Bike Unitard ($78)

12 of 12

Her Pretty Pink Wedding Dress

We're often stumped when it comes to wedding guest outfits, but the pale pink ensemble that Cher wore to Mr. Hall and Miss Geist's big day would work for a variety of venues.

Shop It: Macgraw Romantic Silk Short Dress ($799); Stuart Weitzman Gala Maryjane Flat ($425)

Was this page helpful?