Never Been Kissed, the iconic rom-com starring Drew Barrymore as a journalist who goes undercover as a high school student to report on teens, has everything: prom; an ensemble cast of greats like Molly Shannon and John C. Reilly; an inappropriate student-teacher relationship with Michael Vartan, and of course, fashion from the 80s and 90s. What's not to love?
Barrymore plays Josie Geller, a mousy 25-year-old grammar nerd who serves as the Chicago Sun Times' youngest copy editor but dreams of becoming a serious reporter. After landing her first undercover assignment at a local high school, Josie must reckon with her own traumatic high school memories of an adolescence spent being bullied and called "Josie Grossie." Based on her flashbacks, Josie was bullied for her extreme geekiness and fashion choices.
But as we know, fashion trends are cyclical—the 80s had a comeback in the early aughts, and we're now living in a rebooted 90s dream of chokers and slip dresses. So what was off-trend in 1999—when Never Been Kissed was released—is the height of fashion today, making then-roastable Josie Grossie a style icon if 2018.
Here are five looks that were supposed to illustrate Josie's lack of fashion, but actually just prove her prescient taste:
1. Culottes/Gaucho Pants
Josie wears these wide-leg pants twice within the first half hour of the movie, first in a red matching set, then in blue with a cream button-up. "Are those shorts or a skirt?" Her brother Rob asks her. "They're gaucho pants," Josie answers, before proudly adding, "I got them on sale."
These days, you can't walk a New York City block without seeing a woman in this style of pant.
2. Sneakers and Athletic Socks
In a flashback to her high school years, Josie wears an reeboks with athletic socks (above) when her classmates pranked her by pouring soda into her backpack, which leaked out of her bag and made her look like she was peeing. Today, this look is back with the reign of athleisure.
3. Monochrome with a Feather-Trim
We demand fashion justice for Josie's chic-as-hell all-white feather-trim look that would fit right in at Savage x Fenty.
4. Black Dress with Built-In Choker
In an unforgettable scene, Josie unknowingly eats a pot brownie and hops on stage to dance in dress with a built-in choker—an entire genre of dress at Fashion Nova. Our fashion icon pairs the dress with white go-go boots and even grabs a pink boa before doing a split. Iconic.
5. Short-Sleeve Button-Up Shirt
May the button-up dad shirt never die! Below, Eva Chen (director of fashion partnerships at Instagram) rocks a floral one: