My Favorite Going Out Tops For Spring Are Inspired By Y2K Movies

Jawbreaker will go down in fashion history.

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Cameron Diaz, Selma Blair, Christina Applegate
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Jeans, heels, and a “cute” top. For the better half of the 2000s, this formula never steered me wrong. I’d throw on my bootcut denim, a slinky halter (à la Jennifer Lopez), and some strappy sandals and I was ready to roll. Fast-forward some 20 years later, my long nights of dancing until dawn are few and far in-between. But that’s not to say I don’t enjoy an evening out with friends in which I can trade my sweatpants and oversized tees for something a bit more formal and fun. And, as it happens, Gen-Z’s recent obsession with all things nostalgia has put my old going out tops of yore back on the style radar. So, in prepping my roster for spring and summer, I’ve been taking a trip down memory lane to the films and pop culture icons that originally inspired my look two decades ago. I’m happy to report, there’s still magic to be found.

One film that has remained a constant source of inspiration over the years is the 1999 dark comedy Jawbreaker. A favorite among the fashion set, the film’s candy-coated costumes epitomized the early aughts saccharine. Currently, I’ve been eyeing the fitted cropped cardigans that were the signature. of bad girl Courtney Shayne (played by Rose McGowan). When paired with of-the-moment capri pants, kitten heels, and dainty accessories, this top is still a can’t miss.

Another 2000s icon to turn to for all the fancy top inspiration is Cameron Diaz. Although she’s keeping a low profile these days, the actor was flying high in the early aughts thanks to cult films like Charlie’s Angels and The Sweetest Thing. In addition to her comedic prowess, we can credit Diaz for putting asymmetrical tops on the map, a signature style she wore in many of her films from the decade. I still love the look of this one-shoulder silhouette, and apparently so do labels like Norma Kamali and The Sei, who’ve recently embraced the top in their collections.

There’s much more cinematic inspo where that came from. Ahead, Y2K’s fashion-filled movies that are guiding the top trends for the season.

The Cropped Cardigan

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Long before Barbie mania, there was Fern Mayo’s (played by Judy Greer) iconic pink-infused glow-up, as well as the sugary sweet looks of Jawbreaker’s murderous queen bees. As a teen, I personally gravitated toward the monochrome skirt sets worn by villain Courtney, which typically included fitted cropped cardigans in rich royal hues of red and purple. For modern day, the sweet top adds a youthful, schoolgirl-like touch, especially when accessorized with neck scarves and fun charm jewelry.

The One-Shoulder Wonder

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Whether she was kicking ass in Charlie’s Angels or dancing the night away in a San Francisco club with Christina Applegate in The Sweetest Thing, you can bet Cameron Diaz was wearing some iteration of a one-shoulder top. The actor’s go-to silhouette is still alive and well for 2024, coming in long, flowing versions to layer over denim or more fitted printed styles to tuck into roomy trousers.

The Graphic Baby Tee

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While quirky cropped graphic tees may seem to skew more casual at first glance, Mean Girls taught us otherwise. HBIC Regina George iconically wore the It girl staple with leather mini skirts and heeled slides — so now I’m going to wear them with leather mini skirts and heeled slides. Luckily, tongue-and-cheek tees are making a big comeback this year thanks to brands like Mother Denim, Jacquemus, and Anna Sui, so there are plenty of options to pull from.

The Button Down


As a young journalism student in 2003, How To Lose A Guy In 10 Days protagonist Andie Anderson (played by Kate Hudson) epitomized life goals in every respect. In addition to her glamorous career as a magazine columnist, many a millennial coveted her work wardrobe which consisted of fitted button downs, which were paired with pencil skirts and pumps. The look was put-together and polished while still reading fresh and stylish. I’ve never lost my love and appreciation for the classic button-down. While the last few years has seen the top go more oversized and boxy, these days, I’m reaching for more slim and tailored versions in lightweight, gauzy fabrics to tuck into high-waisted slacks and skirts for a breezy take on office dressing.

The Humble Halter

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You can’t discuss early millennium trends without mentioning halters. The back-exposing top was truly everywhere and on every big screen startlet. The 2008 comedy The House Bunny championed the style, with the film’s well-meaning lead Shelley Darlingson (played by Anna Faris) often pictured skipping around her college campus in one. While the film’s terry cloth iterations may have fallen by the wayside, the top is getting a modern upgrade, with striped, taffeta styles and handkerchief silhouettes coming into view for spring. Shelley would certainly approve.