Drew Barrymore's Outfits in Never Been Kissed Are So Delightfully 2019


It's been two decades since 1999's Never Been Kissed was released, but don't let that fool you into thinking we had completely forgotten about Drew Barrymore's style in the movie. It may not be the most remembered of '90s-era movies (we see you, Clueless), but it was nonetheless filled with style moments that you'll soon see are just as relevant today as they were then—specifically, the outfits Barrymore's character wore.

If you have never seen the movie or it's been years, it follows Barrymore's character as a 20-something reporter who goes undercover as a high school student as research for a story. While attending English classes and attempting to find an in with the cool girl clique at her new school, we see her character, Josie Geller's, outfits start to conform to the '90s teenage girl aesthetic that consisted of things like cardigans, slip skirts, and other items you'd easily find in the closets of fashion girls today.

The point I'm trying to make is that Never Been Kissed–era Drew Barrymore is actually a wealth of '90s style inspiration that I think you'll agree with me feels relevant today, too. Keep reading to see which trends she wore in the movie and shop the 2019 versions of each.

Fluffy Feathers, Please


(Image credit: Rex Features)

Despite the angst-infused frown Barrymore's character is wearing here, we're still so into her feathery white concoction of a top. It was likely so extra set against a 1999 high school cafeteria, but for 2019, feathers are a fashion girl's best friend. To be honest, if the exact top were available today, we'd have already added it to our carts, but alas, the internet is rife with pretty options, some of which you'll find below.

Ditsy Floral Prints Galore


(Image credit: Rex Features)

Romantic white floral tops may not have been as ubiquitous as they currently are when Barrymore styled them in Never Been Kissed, but this is proof that the breezy piece makes for the perfect match to jeans.

Cardigans in Every Color of the Rainbow


(Image credit: Rex Features)

Did Barrymore and her teenage crew time travel to 2019 when filming Never Been Kissed? From the look of it, yes. How else would they have known that wearing your cardigans buttoned all the way up as a top was the coolest thing since sliced bread? We're way into the styling here with slip skirts (so very '90s) and the array of colors they chose for the knits.

For more of the film fashion icons we love, here's why we're so into Diane Keaton's outfits at the moment.

Senior Editor

Anna is an editor on the fashion team at Who What Wear and has been at the company for over five years, having begun her career in the Los Angeles office before relocating to New York, where she's currently based. Having always been passionate about pursuing a career in fashion, she built up her experience interning at the likes of Michael Kors, A.L.C., and College Fashionista before joining the team as a post-graduate assistant editor. Anna has penned a number of interviews with Who What Wear's cover stars over the years, including A-listers Megan Fox, Issa Rae, and Emma Chamberlain. She's earned a reputation for scouting new and emerging brands from across the globe and championing them to our audience of millions. While fashion is her main wheelhouse, Anna led the launch of WWW Travels last year, a new lifestyle vertical that highlights all things travel through a fashion-person lens. She is passionate about shopping vintage, whether it be at a favorite local outpost or an on-the-road discovery, and has amassed a wardrobe full of unique finds. When she's not writing, you can find her shooting street imagery on her film camera, attempting to learn a fourth or fifth language, or planning her next trip across the globe.