Feeling Fancy: The “Clueless” Fashion Trend

Last spring, I was in New York to consult on the fall buy for TSALT, where we took appointments at a variety of showrooms. The Globe Showroom is always a favorite since this is where Smythe resides. It didn’t take long before I zoned in on my next favorite blazer for fall.

I’m not sure if it resonated immediately but upon seeing images from the Fashion Week shows, I knew what the draw was. I was no longer clueless but feeling quite fancy about my choice. Cher Horowitz lives!

One of my favorite fashion movies of all times is, without a doubt, Clueless. Let’s just talk about Cher’s virtual closet for one sec…I mean, I was fully convinced this was the way of the future. Little did I know I would be creating outfits out of my clients wardrobes with a little camera in my phone 20 some odd years later. There’s still some headway to be made in closet-style solutions! Thankfully, this still resides within the creative energy of a passionate and talented stylist. 😉

When Cher and Dionne made their entrance on the first day of school in plaid mini skirt suits, my style brain exploded. Mona May was the movie’s costume designer and Amy Heckerling (of Fast Times at Ridgemont High) was the director. The movie is loosely based on Jane Austin’s 1815 coming-of-age novel Emma. Heckerling wanted the clothing to have an important role in the movie in order to tie in the sophomoric comedy where characters would rag on each other’s clothing in true high school fashion! Dolce & Gabbana designed the iconic yellow plaid mini suit that Cher wore as she strutted the hallway of Beverly Hills High School like a supermodel on the runway stage.

For the record, when this film was released in 1995, the style of the day was was in full Kurt Cobain grunge mode. May and Heckerling checked out what kids were wearing in Beverly Hills area high schools and found it was quite uninspiring. The girls of this era were in over-sized clothing that was lacking femininity. The plan was to have Cher and Dionne exude that love for fashion that only 16 year olds with the ability to go to the European shows on Daddy’s private jet could display.

And quite the display it was! Clueless kicked off a new wave of preppy minimalism by way of super short kilts and over-the-knee socks. Mona May explained that while Alicia Silverstone had 60 costume changes, those over-the-knee socks pulled the looks together for her character. There was a fashion cultural shift with Clueless that gently nudged me from my over-sized shirts, true boyfriend Levi cutoff shorts (with black tights and Doc Martins in the winter, of course), and had me reaching for my scissors as I shortened every one of my mother’s kilts from the 50s.

Somewhere between grunge and “new” preppy might have been one of my favorite blends in fashion. The most satisfying parts of style for me are the in-between moments. It’s never the destination but the process involved in getting there. This is where the magic happens.

Let it be known that this movie brought us more than great fashion moments…


When Clueless was being cast, Reese Witherspoon read for the role of Cher Horowitz. As much as I’m a fan of Reese, no one can hold a candle to Alicia Silverstone’s portrayal of a privileged Beverly Hills-area high school budding stylist.

“Cher’s main thrill in life is a makeover. It gives her a sense of control in a world full of chaos.”

Amen! I mean, what isn’t to love about Alicia Silverston’s Cher?! As obnoxious as she and her friends can seem (keeping in mind this is a coming-of-age comedy), Cher is on the path of discovering the best version of herself with a healthy dose of feminism she tucks away in her mini backpack. If you pay attention to the clothing throughout the film, Cher’s own personal growth is documented through her wardrobe. The over-the-top moments came with great quotes such as,“Dionne and I were both named after great singers of the past who now do infomercials.” As the enlightenment of Cher evolved, her clothing choices toned down as she ultimately finds love with Josh…and I still have a crush on Paul Rudd. There’s nothing quite like his smart humor for a bad day!


Cher has a way of defining other people’s fashion don’ts:


Cher (to Tai about Amber):

“She’s a full-on Monet. It’s like a painting, see? From far away, it’s okay. But up close, it’s a big old mess.”


Cher (to Amber):

“Do you prefer ‘fashion victim’ or ‘ensemble-y challenged?’”


Recently, Alicia Silverstone parodied herself as Cher on Lip Sync Battle:

(I love this show!!)


This fall, Clueless is having another influential fashion moment. Spring Fashion Week unveiled a very memorable moment in plaid, but this time it was through the eyes of Versace…and then many others as well.

It’s a full-fledged, yellow plaid Clueless renaissance that is about to rain down on us come September. It’s a strong look but perhaps one that won’t need to be done in the likes of Cher Horowitz. But I assure you one thing…I’ll be feeling fancy in my Smythe plaid jacket!


Words of Fashion Wisdom from Cher Horowitz


1. Never underestimate the power of clothes.

Key line: “Cher’s main thrill in life is a makeover. It gives her a sense of control in a world full of chaos.”


2. Fashion should be fun.

 Key line: “I must give her snaps for her courageous fashion efforts.”



3. However glamorous you are, sometimes it pays to play the game.

Key line: “Where is my white collarless shirt by Fred Segal? It’s my most capable-looking outfit!”


4. Represent your generation, however dumb the trends are.

Key line: “What did you do at school today?” “I broke in my purple clogs!”


5. Keep your standards high.

Key line: “You see how picky I am about my shoes, and they only go on my feet.”


6. Friends are everything.

Key line: “Did my hair get flat? Did I stumble into some bad lighting?”


7. For eveningwear, ditch the berets and pom-poms and go simple, strong and classy.

Key line: “It’s Alaia!”


  • The latest from Alicia
Alicia was born and raised in Alexandria, and married a local boy. She is happily married and the mother of two amazing children and one adorable and terribly smart border terrier named Dixie. Alicia has always known she was a creative. She collected editions of Vogue from junior high on and has always loved clothing and design. She studied interior design at VCU and parlayed that degree into commercial interior design, the web design, and ultimately found herself managing a local boutique and serving as a stylist to many Alexandrian women. She now has a successful full-time styling business, The Tulle Box, and makes it her business to make her clients feel great about themselves and the way they look.


  1. Avatar Susan G says:

    So so good! I was smiling the entire time I was reading this post!

  2. Avatar CC says:

    Enjoyed this post! I love the fashion in Clueless & this post really inspired me to try a modern day version ♡

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