Think Plaids & Checks Are Boring? Think Again

There’s a bold new way to wear them.

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PARIS, FRANCE - JULY 05: Maria Bernad is seen wearing cropped cardigan, yellow checkered skirt, micr...

If you’re a plaid and checks fanatic, you’ve indeed noted the traditional prints’ metamorphosis of late. Most famously, these crisscrossing lines in varying widths and colors date back thousands of years and are iconically associated with kilt-wearing Scottish Highlanders and prep schoolers. But, new-season versions capitalize on how checks and plaid oscillate between punk and preppy. The subversive nature of the former drives staples in darker tones and with tattered details, styled in juxtaposition with leather, chains, and chunky footwear. At the same time, yet another nostalgic reference, Ms. Cher Horowitz of Clueless, drives the prim, brighter, and back-to-school-skewing styles firmly at the crux of 2021’s refreshed iterations.

“We’re seeing that summer’s cottagecore and tennis trends are transitioning perfectly into this fall season, now showing up as classic prep and schoolcore looks, mainly featuring the checks and plaids print,” says Caroline Maguire, Shopbop’s fashion director, whose well-known for wearing bold and dynamic plaid outfits. “We’ve seen this really shine through in the form of checkerboard blazers and pleated or flowy plaid skirts paired with simple blouses, oversized sweaters, ankle socks, and chunky loafers.”


Though most checked and plaid pieces feel inherently polished, the newest patterns differ by offering a more joyful approach to the timeless motifs, removing any presumed stiffness or dullness. “I’m loving the way designers are modernizing these nostalgic prints through the mix and matching of additional designs and colors, incorporating bold hues — think bright greens — retro florals, and crafty patchwork,” Maguire tells TZR, a look quite in line with the sweeping Y2K aesthetic. “These details give a contemporary feel to a classic look,” she adds. “Isabel Marant, KITRI, and Marni, to name a few, have delivered this season on keeping these prints fresh and fun.”

While a single plaid piece mixed with basics is an easy way to dip your toe into the world of vibrant fashion, Maguire encourages a more-is-more approach — right up a maximalist’s alley. “Add some dimension to your look by layering different textures, prints, and colors together for an elevated fall fit,” says Maguire. “Focus on what makes you feel good and have fun with it.” She suggests another simple tip: start with complementary colors, like two brown and red plaid patterns, and build your look from there. An easy pop to finish the look would be a vibrant, contrasting solid piece.

Ultimately, the fashion director says anything goes when styling checks and plaids, but she most enthusiastically urges a “dare to be different” mentality when getting dressed. So ahead, lean in by discovering eight plaid and checked pieces worth adding to your fall wardrobe, in various colors, silhouettes, and textures.

We only include products that have been independently selected by TZR’s editorial team. However, we may receive a portion of sales if you purchase a product through a link in this article.

Plaid Tops

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This season’s plaid tops are about high impact, from two-toned and frilled designs to bright tones and re-worked silhouettes. Team yours casually with jeans or style them in a monochromatic fashion with additional prints.

Plaid Pants

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The plaid trouser is an iconic piece in any preppy wardrobe. Revive your collection with brightly-colored silhouettes with wide legs and finish with chunky shoes for ample drama.

Check Blazers

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Think plaid blazers are boring? As if. Look to vivid shades like pink and yellow (very Cher Horowitz) for a bolder play on the timeless pattern. Similarly, exaggerated silhouettes lend a modern touch, whether paired with denim, trousers, or a matching skirt.

Plaid Skirts

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From mini to midi, the plaid skirt instantly gives off school-girl vibes. A pleated mini feels super nostalgic, while mix-and-match prints and bright, oversize checks instantly modernize the look.

Check Dresses

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For feminine tastes, a dress is the ultimate plaid piece. Bright colors ensure a seasonally appropriate look that pops, whether you’re fond of a babydoll, A-line, or shirtdress silhouette.

Plaid Shackets

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The shacket — aka a shirt jacket — is here to stay, and plaid versions are a particularly relevant piece this season. Style one over a tee with jeans and chunky loafers for a relaxed look. Or, layer one over a fitted dress with tall boots for something a bit dressier.

Check Knits

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The coziest rendition of checks and plaids is undoubtedly knitwear. These pack a decidedly preppy punch, whether you opt for a cardigan, pullover, or sweater vest.

Plaid Coats

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If you purchase one vibrant plaid piece this fall, make it a coat. You can toss it on over a sweatsuit, dress, or denim ensemble and make a statement in one fell swoop.