ONE AND DONE With some savvy styling, a vibrant pink dress can be worn throughout all four seasons. See below for full shopping credits.

Photo: F. Martin Ramin/The Wall Street Journal, Styling by Lynette Pone, Hair by Juli Akaneya, Makeup by Mollie Gloss, Model: Emilli Cestari/ Elite

FOR MARGE SIMPSON or Wilma Flintstone, a single dress suffices for any season, be it a Springfield summer or prehistoric winter. In real life, most dresses lack that versatility. A long-sleeved, stretch-wool Alaïa sheath might be a winter mainstay, but wear it in June and you’ll be drenched with sweat. Gabriela Hearst’s sleeveless, blue linen midi deserves to get out a lot in August, but it’s not so hot an option come frigid February.

Fashion’s longstanding seasonal business model—one that demands shoppers buy new clothes when the weather shifts—puts a strain on women’s wallets, closet space and smartphone calendars. “As someone who loves fashion…I’ve had a lot of frustration [around having] to rotate through different dresses during the year,” said Darcy Shapiro, 40, an insurance technology executive in New York. Laura Mortensen, the New York-based president of communications agency Sharp Think, doesn’t have the bandwidth to constantly update her wardrobe. “I have two little kids so in general, my shopping time is pretty limited,” said Ms. Mortensen, 36. When shopping, “I’m kind of on a mission and focusing my time [on] getting a few key things.”

Her missions might soon become more possible. Designers—responding perhaps to global warming, constantly traveling clients or just women’s needs—are increasingly sending seasonless collections down the runway. For spring, Celine’s lineup is filled with mid-weight dresses flexible enough to weather a range of temperatures, while Agnona proposed light cashmeres and crepe de chines, fit for any climate.

‘The seasonless dress doesn’t need to be basic or simple or boring.’

New York- and Los Angeles-based stylist Beverly Nguyen, 29, said her clients expect to be able to wear their fashion purchases year-round. She advised that silk, crepe and cotton poplin dresses will carry you the farthest, especially those with simple silhouettes, “good for dressing up or down.” As for color, resist shrill yellow or particularly vocal shades of green. It’s easier, she said, to layer a sleeveless dress in a quiet hue over a bright turtleneck or silk blouse in fall or winter.

Saks Fifth Avenue fashion director Roopal Patel, whose customers want dresses that have “multiple uses,” cautions against too much restraint when it comes to styling. “The seasonless dress doesn’t need to be basic or simple or boring,” she said. Her go-to is a navy slip dress by Zimmermann that she layers over a tank top on sticky summer days; in the winter, she’ll toughen it up with a moto jacket and combat boots.

Adaptability is key. The world’s most attitudinal leather jacket won’t make a white eyelet baby-doll fit for fall. Ms. Patel’s navy number is an ideal four-season dress because it’s neutral enough to lend itself to styling tricks. Espadrilles make it July-ish; wool tights cozy it up for November.

Often made in printed silks or cottons, New York designer Ulla Johnson’s bohemian dresses are strong contenders for fans of feminine, trans-seasonal pizazz. “We had a georgette dress from pre-spring that I wore in Uruguay on the beach with sandals and then I wore it in the city with boots and a coat,” said Ms. Johnson. “Same dress, one week later.” She suggested that most garments can be worn outside of their assigned seasons—it’s all about “the point of view of the wearer,” she said. That, and maybe some creative layering.

THREE FOR FOUR / FROCKS FIT FOR YEAR-ROUND WEAR

From left: Dress, $465, self-portrait-studio.com; Dress, $498, toryburch.com; Dress, $3,400, prada.com.

Photo: F. Martin Ramin/ The Wall Street Journal, Styling by Anne Cardenas

On Model Left: Simple for summer: Roksanda Dress, $1,525, matchesfashion.com; Earrings, $80, jenniferfisherjewelry.com; Bracelet, $75, roxanneassoulin.com; Bracelet, $75, roxanneassoulin.com; Bag, $3,250, Bottega Veneta, 212-371-5511; Sandals, $395, emmeparsons.com. Right: Layered up for winter: Roksanda Dress, $1,525, matchesfashion.com; Turtleneck, $30, uniqlo.com; Theory Blouse, $245, saksfifthavenue.com; Hat, $115, hatattack.com; Loeffler Randall Boots, $695, shopbop.com; Earrings, $265, jenniferfisherjewelry.com.

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.

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