Editor's Picks, Fashion, Movies, Lookbook

The most important and underrated outfits in teen movie history

Deconstructing looks you've definitely seen, but rarely appreciated.

I am here to talk about one of my greatest passions in life: movies created for or marketed to an exclusively teenage, primarily female audience. Often, these films star a female protagonist and her light-skinned-but-not-white best friend. They are always predictable, always clichéd, but never devoid of at least one outfit that convinces you that all your problems too would be solved at the end of an hour and a half of lighthearted banter and surface-level character development if only you owned an exact replica.

These movies take place in an alternate reality — they don’t have to play by the same rules we do, and they overlook these rules most often when it comes to clothing. Teen movies aren’t here to replicate real life; they’re here to elevate it.

And while their efforts are often recognized and applauded, there are certain looks that have not received the appreciation they deserve. So here they are, in list form, ready to be gazed upon, analyzed and (hopefully) acknowledged for the visual delights that they are.

1. White dress, shawl, and John Cusack Say Anything (1989)

A young woman wears a short white dress with a sweetheart neckline and matching white shawl. Her hair is in loose curls with a purple flower clipped to one side.
[Image description: A young woman wears a short white dress with a sweetheart neckline and matching white shawl. Her hair is in loose curls with a purple flower clipped to one side.] Via Bitch Flicks.
The least believable detail in Say Anything by far is that Diane Court—valedictorian, serial overachiever, self-confessed hermit—would attend her first ever high school party in an outfit so well-executed. This outfit is essentially the clothing equivalent of sipping cocktails by the beach all evening, but pacing yourself well enough that you remain in lightly-buzzed territory, never into drunk-ocean-swimming territory.

The beach cocktails are in the purple flower that someone picked up on the beach of a Polynesian Island (probably) and hair that was definitely in rollers a few days ago, so they’re not too perfect (they are perfect to me).

The buzzed-but-never-wasted is all in the dress. Definitely more chic than anything you’d find at a high school party, but not so much that it’s uptight. The neckline says ‘I’m here to broaden my social horizons’, but the length says ‘I’ll do it at my own pace, thanks very much’. And the shawl is to drape tightly around your shoulders when you’re trying to signal to your companion that it’s time to head home or to use as a lasso when you surprise everyone with an interpretive dance to ‘Old Town Road’.

2. Clothes I would refuse to sweat in, Clueless (1995)

Five young women lean against a tennis court fence wearing a variety of monochrome sports outfits.
[Image description: Five young women lean against a tennis court fence wearing a variety of monochrome sports outfits.] Via Well + Good.
Take a minute to really soak in everything about this photo. Look over it slowly, one outfit at a time, really take your time with it all. Finished? Congratulations! You just witnessed the birth of athleisure.

Well before Outdoor Voices and Lululemon hopped on the sportswear-but-make-it-fashion train—Cher, Nose Job Girl, and pre-wannabe-Republican-congresswoman (look it up) Stacey Dash drove it right through Beverly Hills.

The best thing about these outfits is their ambiguity. If the boys playing some kind of sport behind them didn’t give it away, you’d have no clue what any of these girls were up to that day. Yes, they could be playing tennis but they could also be trying out for a roller derby team or waiting in the Porta-Potty line at an outdoor festival or lined up at a cashier buying snacks before watching all four The Cutting Edge movies.

All these women bring something different to the proverbial table, but I am leaning towards Cher’s outfit in particular solely because of the tiny phone-sized gold bag she’s carrying. It is my prediction that tiny bags in 2019 will get smaller and smaller until somewhere, someone will manufacture an exact replica of this one and I will give them lots of money for it.

3. If Beyoncé was an outfit, Life Size (2000)

A tall, black woman and white man stand facing each other and looking towards the camera. The woman's hair is pulled back and in voluminous curls, and she wears a red satin dress with a black lace bodice and matching shawl. She is also wearing a pair of dangling diamond earrings.
[Image description: A tall, black woman and white man stand facing each other and looking towards the camera. The woman’s hair is pulled back and in voluminous curls, and she wears a red satin dress with a black lace bodice and matching shawl. She is also wearing a pair of dangling diamond earrings.] Via Pinterest.
Did you experience a sharp intake of breath the moment you saw this picture? Did you feel that you needed to look away for a minute, before looking back again? Did you also never, ever want to stop looking? Ugh, same.

Tyra’s wardrobe in this movie is so perfect it makes me want to slap myself. Her character, Eve, is a doll come to life, but her outfits strike the perfect balance between sickly sweet perfection and surprising everyday wearability. There are lots of gowns—the blue mermaid gown with the butterflies, the pink gown on the movie’s poster—but this particular one makes me want to slap myself the hardest.

I wish there were photos of it from every angle available on the Internet because that’s what this dress deserves. Not visible in this image: elbow-length black gloves (slinky!) with a diamond cuff over one wrist (sophisticated!). And that black lace bodice exposure over just the one boob! Revolutionary.

This is a Power Dress. It is the dress you would put on in preparation to do something that requires every ounce of confidence you can muster, like asking for a raise, or proposing marriage, or telling a restaurant server that you can kind of taste mayonnaise in your food even though you specifically asked for it without, and you’re sure it’s an accident but if they could do something about it that would be great and if not that’s fine, too. Your raise will be secured, your proposal accepted, and your mayonnaise eradicated. It’s what you deserve.