If Never Been Kissed taught us anything as tweens, it was that there is a difference between being kissed and being really kissed. When Josie Gellar describes being really being kissed she says, “That moment when you kiss someone and everything around you becomes hazy and the only thing in focus is you and this person, and you realize that that person is the only person you’re supposed to kiss for the rest of your life.”
The ever-so-adorable 1999 rom-com inevitably brings back memories of high school. Whether they were your glory days or the worst days of your life, questionable fashion choices and teenage nostalgia go hand-in-hand, and Never Been Kissed is brimming with flawless and cringeworthy 90s outfits.
We’ve compiled a list of the 15 best looks from this “totally rufus” film.
1. All White Everything 
Josie has guts wearing an all white feathered ensemble on her first day as a fake 17-year-old high school senior. She doesn’t really pull off her mission of remaining low profile, as she shows up looking like a giant chicken and then spills chocolate milk down her pants, but it does get fellow high schoolers like Guy Perkins to notice her.
2. Exposed Chests Galore 
Guy Perkins is the typical high school stud who ends up “crunching” on Josie and taking her to prom. (What an idyllic opportunity for a 25 year old to redo her miserable first prom experience!) In typical dreamy dude fashion, Guy has a passion for tight jeans and open shirts that reveal his hairless man chest and make us feel uncomfortable in retrospect, when we realize he’s only 17.
3. Printed Sweaters 
This floral sweater look is debuted nearer to the point in the film where Josie isn’t “Josie Grossie” anymore. As a symptom of her slow transformation into a cool chick, Josie does away with feathery accents and steps up her style with some trendy 90s pieces. Thanks to the cyclical nature of fashion, floral sweaters and red lipstick are on trend once again, and Josie Gellar helped to pave the way.
4. Mr. Cool-son
Given that Michael Vartan plays Sam Coulson, Josie Gellar is more than justified in falling in love with him. (We cannot excuse Mr. Coulson, however, for making moves on a student he thought was 17.) Nevertheless, Coulson is a foxy English teacher with a swoon-worthy grasp of Shakespeare and an equally dapper wardrobe full of respectable polos. It’s just the right combination of style and depth for any 90s stud muffin.
5. Anita Glam: Animal Prints & Bold Colors
Anita works with Josie at the Chicago Sun Times and is a bit of a loudmouth. She is the kind of person who sneakily leads a Sex Ed class and really enjoys it. Obviously, Anita is bold and maybe slightly unhinged, and so is her sense of style. All of the statement trends of the late 90s (red blazer, red roses, cheetah print) come together here for one audacious look.
6. The LBD: Cut Out Friendly 
When Josie is trying to get in with the cool kids, she crashes their hangout at a local club. She sports this black dress that fully embraces the 90s built-in choker look, pairing it with white go-go boots and a pink feathered boa. Because, when you’re dancing on stage with Ozomatli and accidentally doing edibles, why not?
7. Cardy Party 
Friends who match together, stay together. Kirsten, Kristen and Gibby adopt Josie as a sort of project. In true makeover movie fashion (ie: Clueless, She’s All That) the popular trio helps Josie spruce up her look via colorful cardigans, printed tanks and lots of mall montages of best friends holding pinkies.
8. My First Prom: Metallica Edition 
Photo via Topshop
Josie Gellar’s painful prom flashback proves the awfulness of her adolescence. Billy Prince, her high school crush, asked her to prom and then cruelly egged her as she stood helpless on her front porch. While Billy is a jerk forever, Josie’s pink taffeta prom dress was probably egg-proof. Not the prettiest dress ever, but an original for sure.
9. Crochet Crop Tops 
Ah, the crocheted crop tops, citrus colored everything and general lack of fabric occurring here. So good. Also, so unbelievable that even someone as hot as Jessica Alba would get away with wearing that to school, but we digress.
10. Aldys in Wonderland
Aldys (Leelee Sobieski) is a science fiend and therefore misunderstood by her “cooler” peers. At prom, Aldys dresses up as the DNA double helix with her other science pals, but when she takes off her suit to dance to “Please Please Please Let Me Get What I Want” by the Smiths, she strips down to just a blue bodysuit. While not typically sexy, the whole ordeal is pretty mesmerizing and a precursor to early American Apparel ads.
11. Poncho Villa 
For her weirdly-inappropriate-but-also-cute carnival date with Mr. Coulson, Josie rocks a black poncho layered on top of a dark frock to create a romantic but practical look. This is one of the few times the confusing hybrid of knit blanket and large doily that is the poncho does not make us cringe.
12. Dress for Success
The peasant top, the flirty floral sundress and the spaghetti strap tank are all glorious products of 90s fashion, and essential to any wardrobe inspired by nostalgia. Also essential: Wednesday Adams bangs and general abuse of tiny hair clips.
13. Barbie goes to Prom
The “prom scene” is key to any teen movie, and Never Been Kissed gives a classic example of a costume ball gone awry. Kristen, Kirsten and Gibby all rip off each other’s Barbie costumes and end up bickering over who originally decided to be the scantily clad children’s doll. The scene makes for classic valley girl banter and some excellent gold lamé bustiers.
14. No Fear Shakespeare: Guy & Josie 
Josie’s second prom obviously has to make up for her first. She and Guy go as Shakespearean couple Rosalind and Orlando from As You Like It, a play on the theme of hidden identities. Josie wears pink again, only this time she looks like a Renaissance beauty, and not 80s roadkill. Hurray!
15. Makeout Dress
Waiting for Mr. Coulson to come and kiss Josie Gellar upon the pitcher’s mound is a moment of intense suspense. (Will her undercover work and subsequent humiliation pay off in the perfect smooch?) As the movie comes to a close, Josie is every bit a rom-com heroine in a pastel pink cap sleeve dress.