I realize all the films I’ve posted so far have been about women battling some kind of life crisis. Not very fun. When I’m feeling blue, I know I can always turn to Clueless. I was fifteen when the movie came out and, fifteen years later, I still get super excited about it. It’s like way cool.

Sure, the columns are way classic, but check out Cher’s silver backpack and matching Mary Janes. 
Other than being part Jewish, it wasn’t very easy to relate to Cher Horowitz, an impossibly adorable California blond that lived in a mansion with columns dating “all the way back to 1972,” and has a fabulous best friend that knows “what it’s like for people to be jealous of us.” But it was so hard to hate her. 
Instead, I was seduced by her charm, her terminology (hello, “As if!” or “Baldwin” and “Betty”) and, of course, her clothes. In the golden age of grunge, Clueless offered a preppy all-American alternative. Of course, kids in California didn’t dress this way. It was kind of a hyper-realised fashion reality. 

OMG, I’m totally buggin’ over the size of those cell phones. But don’t you wish you had a 1995 Jill Stuart plaid suit?

“Dionne and I were both named after famous singers of the past, who now do infomercials.”

“At the time it was very grunge oriented fashion, very Seattle, and we didn’t want to recreate it. We wanted to bring something fresh and new: really bring the school girl prettiness, the femininity of clothes,” explained costume designer, Mona May. “The clothes needed to be very bright and fun. I wanted the girls to be girls again, with over-the-knee stockings and Mary Jane shoes. We wanted to change the current look that was on the street and show teens how to have fun with clothes.”

Sure, the mom is a total “Betty” but I can’t stop staring at her Halston dress.  
“Wasn’t my mom a total Betty? She died when I was young. A freak accident during a routine liposuction.”
Cher went through 56 outfit changes, each impeccable in its own way. From her, and Dionne’s,  signature plaid suits (most were by Jill Stuart), crisp dress shirts paired with a teeny tiny vest, see-through blouses worn over tank tops, to her slinky dresses and even her workout attire, Cher was a girl that knew how to put an outfit together. Of course, we can credit her styling genius to her groundbreaking software. 
Didn’t you like totally wish you had one of these?
What really made the ensembles were the fine details: headbands, jewellery, hats (especially Dionne’s), bags and backpacks and the ever present over-the-knee stockings. They would put Blair Waldorf to shame.
All-American: red, white and blue. 
“I feel like such a heifer. I had two bowls of Special K, three pieces of turkey bacon, a handful of popcorn, five peanut butter M&M’s and like three pieces of licorice.”

French-inspired Cher and crazy-hat Dionne.
The cell phone chain bag is way awesome. I wonder if it’s Chanel like my darling bottle holder?
“Do you prefer ‘fashion victim’ or ‘ensemble challenged’?”

Headbands, minis and dress shirts: preppy as it gets.

There were a couple of fashion history-making moments: 1) the introduction of Alaïa to the general public with the phenomenal red bandage dress (“He is like a totally important designer,” Cher told us); and 2) the confirmation that Calvin Klein was the most provocative designer of that era.
The famous red Alaïa was paired with a jacket by costume designer Mona May.
“Oh, no. You don’t understand, this is an Alaïa!” 
She should have known that Christian was gay, like any man able to resist this Calvin Klein number.

Mel: “What the hell is that?” Cher: “A dress.” Mel: “Says who?” Cher: “Calvin Klein.”

Aside from clothes, Cher’s cluelessness was something many of us teenage girls could identify with. How did we not know that our best friend was secretly in love with us (☑) or that the guy we were like totally into was actually gay (☑)? Or that what we were looking for was right in front of us this entire time (☑) ? 
As if!