The Best Plaid Skirts Are Tools for Self-Expression

Plaid is one of fashion’s most evocative prints. It's synonymous with the fall season, an essential preppy code, and a sartorial tool for subversion (the print, as you know, has a prolific history in the punk scene). To narrow it even further, skirts done in the checked print are particularly symbolic. Ranging from a rebellious grungey attitude to a bookish, back-to-school spirit, the best plaid skirts make you feel something. As fashion and design historian Michelle Tolini Finamore explains, the silhouette is a worthwhile reminder of clothing's capacity for self-expression. 

"The versatility and varied meaning of plaid is so fascinating! The cover of 1980s The Official Preppy Handbook is—you guessed it—plaid," she says, with the print representing "'good taste and proper breeding. And I cannot neglect to mention Cher Horowitz's yellow plaid ensemble in Clueless, which has entered into the costume design canon as one of the most iconic ensembles of its era," she explains.

Simultaneously, the pattern can symbolize revolution, acting as a metaphoric middle finger to oppressive social norms and institutions. The fashion historian references Alexander McQueen's FW1995, which heavily featured plaid, particularly tartan kilts. "McQueen was of Scottish descent, and the collection represented the contentious history of British colonization of Scotland. As was typical for McQueen, the symbolic value of wearing plaid, which the Brits had forbidden in the 18th century, was woven into the collection." She also cites Vivienne Westwood's FW1993 Anglomania collection: Channeling her roots of "dressing the Sex Pistols in the '70s in punk versions of plaid, Westwood revisited the print [for the show,] creating her own 'MacAndreas' clan tartan as another subversive act."

The ultimate takeaway here? Plaid can’t be pigeonholed to one subculture or aesthetic. The pattern—especially when done in a skirt silhouette—speaks many languages, and it's up to you to decide what you want to say with yours, whether that's "as if!" or "stick it to the man!"

Ahead, find the best plaid skirts to shop ahead of fall 2023, as well as some street style inspiration to kickstart your stylings.

The Best Plaid Skirts

The Mini Plaid Skirt

A plaid mini skirt works for colder weather thanks to its heavy fabric makeup. For extra coverage, style it alongside knee-high boots or opaque tights and Mary Janes.

The Midi Plaid Skirt

Swap your basic wool midi-skirt for a plaid version. It'll look ultra sophisticated paired with notable classics like a button-down, blazer, and best loafers.

The Maxi Plaid Skirt

Keep your legs warm with a floor-grazing maxi skirt style. Strap on a pair of combat boots and style it with an oversized cardigan to lean into the still-trending punchy punk look.

The Mixed Media Plaid Skirt

Think outside of the box with a plaid skirt that comes in a variety of colors, materials, and alternating prints. For fall 2023, try a short kilt adorned with leather and silver hardware or a longline style featuring patchwork sheers.

Meet the Fashion Expert

Michelle Tolini Finamore

Michelle Tolini Finamore is a Fashion and Design Historian, Curator and Author. She has curated numerous exhibitions, including the recently opened Fashioning America: Grit to Glamour at the Crystal Bridges Museum of American Art. She has written numerous books and articles for both the scholarly and popular press on topics as varied as fashion in silent film, menswear, contemporary fashion, and sustainability. Michelle has taught courses on fashion, design, and film history at Northeastern University, Rhode Island School of Design, Massachusetts College of Art, and the Fashion Institute of Technology. She has interviewed fashion luminaries such as Hamish Bowles, Fern Mallis, Isaac Mizrahi, Liz Goldwyn, Hussein Chalayan, Diane Pernet, Viktoria Modesta, Virgil Ortiz, and Rodarte on stage.