Prediction: This '90s Skirt Trend Will Suddenly Be Everywhere Again

Seemingly out of nowhere, I've noticed a certain skirt trend slowly begin to bubble up, and I think you'll be surprised to find out that it's actually more classic than it is trendy. We've all seen the plethora of plaid skirts worn on-screen during our nostalgic watches of Clueless or Friends, and years later, it seems like the style is still sticking around. While it wasn't a dominating trend on the runways, a few designers like Anna Sui and Tommy Hilfiger drew attention this past fashion month for featuring the style. Also, the ultimate cool label Chopova Lowena has popularized the skirt style in recent years with its highly coveted spliced plaid skirt.

Yes, plaid skirts have a preppy, school-uniform vibe that can't be denied, but they're also more versatile than you might think. Below, I sourced looks from both the runway and street style to give you ideas on how you can incorporate the '90s style into your wardrobe this season. You'll also find the best market options available to shop now. I'm seeing a few pieces trickle into the market. If you want to be ahead of the curve, keep scrolling.

On the Runway

Burberry model wearing brown jacket and plaid maxi skirt

(Image credit: Launchmetrics/Burberry)

It's hard to think of Burberry without thinking of the brand's iconic check. For the F/W 24 collection, designer Daniel Lee reimagined the house's classic print with maxi silhouettes and punchy colors.

Anna Sui model wearing argyle sweater, printed cardigan, and plaid skirt

(Image credit: Launchmetrics/Anna Sui)

With references to Agatha Christie's Miss Marple and the first editions of Virginia Woolf, it only made sense that this Anna Sui collection featured plaid skirts and cardigans styled in a '90s grunge manner.

Tommy Hilfiger model wearing plaid blazer and matching skirt with sheer socks and loafers

(Image credit: Launchmetrics/Tommy Hilfiger)

After a hiatus, Tommy Hilfiger showed again in New York this past fashion month, and the collection served as his love letter to New York. This is evident with the '90s prep classics like rugby shirts, varsity jackets, and, of course, plaid pleated miniskirts.

On the Fashion Set

@balencianas wearing black blazer, white bodysuit, and plaid maxi skirt

(Image credit: @balencianas)

Despite being statement pieces, Chopova Lowena's plaid skirts are extremely versatile and wearable, according to many fashion insiders. They just add an edgy yet cool touch to anything you put on.

@naomielizee wearing plaid skirt and denim jacket

(Image credit: @naomielizee)

Spring outfits stereotypically feature florals or pastels, but this grungy outfit from Naomi is an ideal spring look.

@alyssainthecity in a cream sweater plaid skirt and furry bag

(Image credit: @alyssainthecity)

Channel the preppy look with a cozy cardigan layered on top of a plaid miniskirt. Class is in session!

Shop the Best Plaid Skirts

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Associate Fashion Editor
Yusra Siddiqui is an editor who resides in New Jersey but bounces between the suburbs and NYC. (She's a Jersey girl at heart.) After interning at Who What Wear in 2019, she found her way to the team after graduating from LIM College in 2022 with a fashion media degree. She's also spent time writing and working for publications such as Fashionista, Coveteur, and Nylon, but she always knew that Who What Wear was where she was meant to be. When she's on the job, she's perusing runway shows, analyzing the latest thing fellow Gen Zers are up to on the internet, and sharing what she can about the modest-fashion market. You can also catch her dabbling in entertainment, talking about the costume choices of the latest Netflix series or diving deeper into how the plotline affects the viewers in a myriad of ways. Lastly, she likes to create content for Who What Wear's TikTok. Her personal time is spent doing similar but also different things—deep diving into almost every new TV show (Bridgerton, Gilmore Girls, and Stranger Things are favorites), planning her next local getaway (whenever that may be), and reading the latest Emily Henry or Sally Rooney novel in one sitting.