The little black dress is the closet staple everyone should own. Both classic and flattering, the sophisticated piece is revered for its versatility. Pair it with flats or boots, and it’s the ideal everyday item. Dress it up with pumps, and you can wear it to any evening event. And the best part is that this applies no matter if you’re 26 or 66. However, if you’re in the latter age group, there are certain styles that fashion pros recommend. Keep reading to hear their thoughts on the best little black dresses if you’re over 60, along with simple ways to style each one.
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This is a classic silhouette that’ll serve you year after year. Tara West, a fashion stylist who serves clients in Connecticut, Boston, New York City, and Los Angeles, recommends it especially for the cooler months. “It’s a sharper shape and often comes in beautiful fabrics like merino wool, cashmere, and tight knits to keep you warm,” she says. “Style with a pair of tights and knee-high black boots.” You can find this dress in various hems and necklines and pair it with everything from boots to pumps to flats.
The slip dress is beloved for its versatility—with just one piece, you can create dozens of outfits. “I love the looks of a silk slip midi or a mini dress with a chunky knit sweater thrown over the top or a bright-colored blazer paired with a thick scarf wrapped around the neck,” says West. “A beautiful boot and fabulous earrings will make this look shine.” If you opt for a mini-length hem, West suggests a pair of tights to balance the shorter length. You can walk out the door in minutes!
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The jersey dress is essential for those who value comfort and stylishness. “Any woman with any body shape can be complemented by a beautiful jersey,” says Liana Chaouli, a personal stylist and image therapist. “Find yourself a jersey dress with a three-quarter sleeve to wear throughout the seasons.” You can layer it and style it with any type of footwear and accessories.
This silhouette oozes sophistication. “Every woman over 60 should have a wardrobe of shift dresses,” says Elizabeth Kosich, certified image stylist and founder of Elizabeth Kosich Styling. “The shapeless, straight cut is forgiving, camouflaging, and provides a simple, clean blank canvas to build on.”
Select a sleeveless one for maximum layering opportunities. “Add a light sweater or pashmina wrap in warmer months; a blazer, trench, or overcoat in cooler months; a white shirt underneath year-round,” says Kosich. “Style with a colorful scarf, pendant necklace, or choker at the neck, or strands of pearls for a Holly Golightly look.” It’s an outfit formula you can return to repeatedly.
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Say hello to the most flattering dress you could buy. “A wrap-style dress is flattering to every shape, size, and age thanks to its jersey stretch material that breathes, hugs, and forgives,” says Kosich. “It cinches at the middle to create a waist for straight bodies while emphasizing curves for hourglass figures; the flared hem balances top-heavy shapes and camouflages bottom-heavy ones, and its long sleeves provide arm coverage for all shapes.”
Seriously, what more could you ask for? Kosich suggests styling it with riding boots and a tailored wool coat or heels, statement jewelry, and a wool wrap. It’s a piece that can be dressed up or down depending on the occasion.
Kosich calls the three-quarter sleeve the “miracle” sleeve. “Stopping just beyond the elbow, this truncated sleeve draws attention to—and punctuates—the waistline, which gives the illusion of curves for those without, while emphasizing those who do,” she explains. “It’s also a perfect sleeve for accessorizing—bracelets, cuffs, bangles, watches, or a scarf tied around the wrist.”
You can wear the dress on its own in the summer or with a blazer, vest, cropped jacket, or puffer in the winter. A velvet blazer, tuxedo jacket, or silk kimono makes it appropriate for the evening, she shares. If you’re torn between a few dress options, the one with three-quarter sleeves might be your winner.
