ON A BRISK afternoon last month, my boyfriend looked befuddled as I stepped out of my bedroom. “What’s happening here?” he asked, tilting his head as he stared at my get-up: a tie-dye Proenza Schouler dress underneath a crisp khaki trench from the Gap. “It looks like you couldn’t make up your mind.” The truth was, I couldn’t—so, I didn’t. It was the first time I’d put on a real outfit in over a year, and choosing just one aesthetic was too difficult.

SHARE YOUR THOUGHTS

What pieces are you most excited to wear this summer? Join the conversation below.

Many women are facing a similar predicament as the U.S. opens up and we delve into our long-neglected wardrobes, revisiting the decision processes of getting dressed. It’s hard to settle on just one thing—we want to wear it all. The result is kooky, counterintuitive styling—or artful mismatching—a look that, when it works, is best described as the sartorial equivalent of “chaotic good.”

“I’m eager as hell to get dressed up. I do it to go out for groceries,” said Leandra Medine, a fashion writer in New York known for her mismatching skills. She attributes the trend’s newfound popularity to overexcitement. “Personal style is a meaningful form of self-expression that…was abruptly cut off during the pandemic,” she said. “And after a year of pent-up energy, curiosity, emotion, rage, we’re at a turning point where we can finally take back this form of self-expression.” Ergo, we’re going all out, making our looks as creative as possible.

Unexpected color combinations—like this quintessentially ’70s marigold-and-brown knit and pop-bright sea-foam skirt—stand out on newly crowded city sidewalks. The Wall Street Journal Interactive Edition

Take Morgan Rossi, global client director at LinkedIn in New York. “The only shopping I did during quarantine [was for] truly special pieces,” said Ms. Rossi, 30. “And those are the first things I wanted to wear when we went back to real life.” Impatient to break out her spoils, she’s been piling on multiple disparate buys at once. Recently, she teamed feathery Manolo Blahnik heels with utilitarian Nili Lotan trousers—both lockdown acquisitions—for a family dinner.

Less expert dressers need to use more strategy when it comes to the mismatch endeavor, employing equal parts creativity and restraint. The outfit should feel unexpected and effortless, but never thoughtlessly thrown together. It must be cohesive and considered, but not stiffly coordinated. It’s a balance that’s easy to get wrong.

Those who aced high-school algebra might want to adopt Ms. Medine’s formula: “If you’re mismatching aesthetics…bohemian with classic, polished with grunge, I like to set an equation wherein the quieter trend, like polished, takes on two parts [of the outfit] for every one part of the louder trend, like grunge.”

If fractions aren’t your strength, New York designer Rachel Comey advises: “Start slow, baby steps.” Begin by wearing patterns you “normally wouldn’t, and see how it feels,” Ms. Comey said. Classic prints—stripes, polka dots, plaids—are a good entry point because they play well with other patterns. You can also stick to one motif and experiment with scale, for instance mixing overblown and minuscule polka dots, as demonstrated below in “On the Dots.”

Clashing prints in shades of citrusy lime make a morning commute more fun. The Wall Street Journal Interactive Edition

More confident clashers create outfits that have a subtle connective thread running through them—like the petal-pink color of two different floral prints or the ease of a billowing blouse and breezy gym shorts. The look’s barely perceptible cohesion lends it an “I don’t know why but it works” quality.

Ms. Medine mused that the mismatch approach reflects the many, sometimes incongruous, roles women play: “The complete look hits so many different identities…in a way that says, ‘I’m all these things.’”

I’m not sure what identities I was straddling with my trench-coat-and-tie-dye look. Perhaps that of a freewheeling, slightly poser-ish hippie (the dress) and that of a sensible adult who’s got her life together (the trench). But this is the beauty of dressing up—it allows us to try on different, opposing identities as a way to explore ourselves.

With that in mind, this sensible hippie plans to stay the mismatch course. And no guy’s grimace can dissuade me.

MADAM MIX-A-LOT

A foolproof guide to pulling off 6 clashing clothing combinations

Shirt, $188, hopeforflowers.com; Skirt, $1,530, Miu Miu, 212-641-2980; Sunglasses, $350, lowercasenyc.com, Sweater, about $720, mollygoddard.com; Shoes, $795, Salvatore Ferragamo, 212-759-3822

Shirt, $188, hopeforflowers.com; Skirt, $1,530, Miu Miu, 212-641-2980; Sunglasses, $350, lowercasenyc.com, Sweater, about $720, mollygoddard.com; Shoes, $795, Salvatore Ferragamo, 212-759-3822

On the Dots

Layering macro and micro polka-dots is double the fun, but flubbing this combo could trigger vertigo in passersby (objectively un-fun). Take a cue from the balanced ensemble above and pick one color for all your spots. The resulting look will elicit smiles, not swoons.

Vest, about $410, rejinapyo.com; Skirt, $685, coperniparis.com; Bag, $1,590, Balenciaga, 212-328-1671; Shoes, $650, manoloblahnik.com

Vest, about $410, rejinapyo.com; Skirt, $685, coperniparis.com; Bag, $1,590, Balenciaga, 212-328-1671; Shoes, $650, manoloblahnik.com

Try the Time Warp

A seemingly dated 1970s palette of brown and orange can feel surprisingly current when paired with cheerful pastel tones like lavender or sea foam. Try a bold knit sweater like this with a simple silky wrap skirt or preppy pink chinos instead of grabbing that same old pair of jeans.

Shirt, $128, ralphlauren.com; Pants, $1,495, chloe.com

Shirt, $128, ralphlauren.com; Pants, $1,495, chloe.com

The Odd Couple

Do you have floral pants idling in the back of your closet? No? Well, find some and pair them with a classic striped Oxford. A shared timeless quality is what makes these seemingly discordant patterns work ensemble. And like any good couple, they bring out the best in one another: The floral pants lend the shirt excitement, and the striped shirt subdues the statement-making pants.

Sweater, $195, rebeccataylor.com; Blouse, $990, Salvatore Ferragamo, 212-759-3822; Skirt, $3,100, Dior, 212-931-2950; Shoes, $295, caroncallahan.com

Sweater, $195, rebeccataylor.com; Blouse, $990, Salvatore Ferragamo, 212-759-3822; Skirt, $3,100, Dior, 212-931-2950; Shoes, $295, caroncallahan.com

Color Theory

Mixing patterns takes practice. Novices should try layering different prints in similar colors, which will create cohesion. For example, this cardigan, plaid skirt and floral top are in sync because they feature kindred shades of green.

Rachel Comey Shirt, $375, Kick Pleat, 512-445-4500; Skirt, $890, carolinaherrera.com

Rachel Comey Shirt, $375, Kick Pleat, 512-445-4500; Skirt, $890, carolinaherrera.com

Opposites Attract

If there were ever a time to reject taboos about wearing activewear, a year spent at home in spandex would be it. As we reemerge, try experimenting with pieces in your closet you’ve never thought to pair, like techy, nylon running shorts and a billowy silk top. The fanciful blouse is made more casual by the no-brainer black shorts, and the breezy ease of both pieces ties them together. 

Shirt, $790, proenzaschouler.com; Shorts, $40, nike.com; Shoes, $625, Manolo Blahnik, 212-255-2600; Sunglasses, $350, lowercasenyc.com

Shirt, $790, proenzaschouler.com; Shorts, $40, nike.com; Shoes, $625, Manolo Blahnik, 212-255-2600; Sunglasses, $350, lowercasenyc.com

Flower Trip

Have you amassed a garden’s worth of floral clothing over the years? Don’t feel like you can only wear one at a time. Pick different floral prints with similar base colors—like the white and pink blooms pictured in the outfit here—and pair them confidently for a less predictable summer look.

A classically Midtown striped shirt makes a strong statement when paired with a playful peony print. The Wall Street Journal Interactive Edition

Styling by Rebecca Malinsky, Hair Styling by Ledora Francis, Makeup By Andrew Colvin, Model Viktoria/Supreme

The Wall Street Journal is not compensated by retailers listed in its articles as outlets for products. Listed retailers frequently are not the sole retail outlets.