15 Plaid Outfits to Check Off Your List

From back to school to Clueless-inspired, we've got you covered.

plaid outfits

Design by Tiana Crispino

Plaid, or “tartan,” emerged in Scotland in the 1700s. Geographically separated weavers produced various patterns based on which dyes and materials were regionally available. Much like crests, families and clans each had their own tartan patterns.

The fabric eventually made its way to America, where it became commonly worn by everyone from punks to prep school students. It’s an iconic print that everyone from Twiggy to Audrey Hepburn adored and wore frequently. In the classic film Clueless, Cher and Dion stole our hearts with their two-piece plaid outfits—who didn’t grow up dreaming of selecting a perfect plaid two-piece outfit from Cher’s electronic closet?

Plaid is always having a moment—it’s a print, but it’s also a neutral. You can wear it with anything—you can dress it up or down with ease. It’s a print that’s evocative of cozy flannel bedding and pajamas, and it can be elevated enough to be worn for elegant evenings out.

We can’t get enough of the print, and here we present you with fifteen plaid outfits that are perfect for any occasion—from a quiet day at home to happy hour to formal events.

Back to School

outfit 1

Design by Tiana Crispino

When we think of plaid, we think of the pleasures of back-to-school season—a few new pieces of clothing from Gap Kids and Limited Too, some new face glitter, a fresh planner, and new mechanical pencils. Channel the excitement of the season with an outfit that your inner child would adore.

Pair this Aritzia skirt with a classic button down—we love this pinstripe number by Stine Goya—it’s elevated and iconic. Wear it with a blazer, a pair of knee socks, and a pair of loafers like these by Flattered. Every piece of this outfit is affordable, comfortable, and classic.

Cocktail Hour

outfit 2

Design by Tiana Crispino

Plaid can and should be worn to happy hour—it’s a timeless, elegant print, and it works for every season. Order your signature margarita or martini and raise a glass to the classic print and amazing conversation. If you’re one for celebrating golden hour at classic bars like Musso and Frank or Sunset Tower in LA and Bemelans in New York, plaid can be your happy hour go to.

This peach-toned Free People dress is perfect for a celebratory happy hour at a hotel bar. Wear it with a pair of gold heels like these super affordable block heels or these shining metallic stars by Zara. Add an emerald handbag like this gold-accented Clare V. shoulder bag, or this gorgeous Bottega piece if you're looking to splurge. You’ll turn every head at the bar.


outfit 3

Design by Tiana Crispino

When pondering plaid, it’s nearly impossible to not think about Clueless. Channel Cher and Dion with an adorable two-piece plaid outfit. Such an ensemble is perfect for a day of shopping, a long working lunch al fresco, and early evening cocktails and dinner.

Wear your plaid set with a beret, a leather mini backpack, a pair of knee socks, and a pair of fabulous heeled loafers like these from Donald Pliner. The put together look is sexy, classic, and timeless—it’ll make you look anything but clueless.

Winter Wonderland

outfit 4

Design by Tiana Crispino

Plaid is a perfect print for winter—it’s warm, classic, and sophisticated. Wear this Old Navy overcoat with a pair of slightly flared jeans, a turtleneck in your favorite color, and a great pair of ankle boots for an easy, casual but elegant look that’ll take you from work to dinner without having to change your outfit.

Spring Is in the Air

outfit 4

Design by Tiana Crispino

It may still be freezing out, but spring is on the horizon. Transition into the warmer weather with a tulip-toned plaid dress like this shimmering one from Alice + Olivia. Add a pair of strappy sandals and a colorful bag for a trip to the farmer’s market, strolling through the botanical gardens, spring flings, and early evening oysters. We’re ready for the season of spring blooms, wearing citrusy fragrances, and feeling the first licks of sunshine on our skin.

Pink Perfection

outfit 5

Design by Tiana Crispino

Pretty in pink and plaid? Sold. Pair this Gucci skirt with a white T-shirt and pattered tights for a look that’s ideal for long poolside lunches, a day at the office, an interview, or just a day in the life. Swipe on a matte pink lipstick or a bit of creamy blush, and celebrate your strength.

Gallery Going

outfit 6

Design by Tiana Crispino

Spending the day gallery hopping or getting lost at the Met? Pair an artful plaid creation like this incredible Ottolinger dress with a pair of bold ankle boots for gallery openings. Wear it with an artful bag that will keep your hands free so you can hold a glass of wine in one hand and shake hands with the other.

Date Night

outfit 6

Design by Tiana Crispino

Whether you’re meeting a new person for lobster and wine or it’s date night with your long-term partner, adorning yourself in plaid will leave a lasting impression. This rusty orange plaid dress by Topshop is at once elegant, sexy, and cool. Wear it with these architectural sandals from Looks Like Summer and a pair of long, detailed gold earrings.

Cozy Nights In

outfit 7

Design by Tiana Crispino

Plaid is a cozy fabric—it’s evocative of evenings spent fireside, warm cups of matcha, and hiding under flannel sheets as snow sifts through the sky. Harness the warmth of the fabric and elevate your evenings in by wrapping yourself in a classic plaid pajama set. Team it with a soft pair of plaid slippers then take the look a step further with some plaid socks, and you’ll be a vision as you lounge. Pick a great movie, light a few sweetly scented candles, open a fabulous bottle of red, and celebrate the bliss of staying in.

The Everyday

outfit 8

Design by Tiana Crispino

Plaid is a great go-to fabric for quotidian activities—errands, lunch with friends, a walk through the park, shopping, or working at home. Piece together a polished and comfortable outfit by wearing plaid pants with a simple long sleeve and a pair of comfortable but stylish sneakers like these timeless Comme des Garcons high tops.

Power Suit

outfit 9

Design by Tiana Crispino

Whether you’re spending the day at the office, jetting off for a work trip, or spending the day in meetings, a plaid power suit is a perfect pick. We’re into pairing with a sharp, silky button-down and patent loafers. Bonus? The look is elegant and timeless, so you can wear it to dinner after work without having to change your outfit. Just transfer your necessities into an eye-catching clutch and slip into some bejeweled heels–and, of course, a great pair of earrings.

Black Tie Affair

ooutfittfir 10

Design by Tiana Crispino

Yes, plaid can even take you to the opera, an extravagant wedding, or any other evening affair. We’re head over heels for this Ralph Lauren gown—the velvet top makes it endlessly elegant, the floor-sweeping plaid is breathtaking, and the bow detailing is sweet finish. Pair it with jewel-toned crystal heels and a clutch, and you’re dressed in an ensemble that would make Carrie Bradshaw smile.

Heart of Gold

outfit 11

Design by Tiana Crispino

Plaid can be glitzy. Step into the gold of life in a stunning, head-turning gold dress like this bright Selected dress. Pair it with a golden necklace, a gold handbag, and a pair of golden shoes. This look is a lot, but in the best way.

Fireside Evenings

outfit 12

Design by Tiana Crispino

Headed to a warm hotel bar for cocktails and tartare? Whether you’re going on a date, taking yourself out, or meeting your best friend for a warm evening in a luxurious setting, dress the part in this plaid Farm Rio piece, which fuses plaid with a warm tropical print. Add a pair of classic ankle boots and tights for an easy and refined look.

Dinner Al Fresco

outfit 13

Design by Tiana Crispino

Dining outdoors? This navy dress from Sea paired with matching ankle boots is ideal for a long, early evening meal alone or with friends. Dress it up a bit with a stack of pearl bangles for even more of a seaside feeling. This is the perfect outfit to wear for an evening of raw bar, fabulous cocktails, and laughter. It’s also a great outfit for transitioning into the warm weather seasons.

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