These Wardrobe Staples for Women Over 50 Were Hand-Picked by Style Experts

While trends can be fun and help you find new items you may not have previously considered wearing, Wise suggests avoiding items just because they’re on-trend or because younger generations are wearing them. “Stay true to yourself and your personal style and you’ll always look good,” she adds.

Meet the experts: Cindy Conroy, fashion expert and celebrity stylist; Leah Wise, fashion stylist and influencer; and Cassandra Sethi, personal stylist and founder of Next Level Wardrobe

Ahead, find our style experts’ favorite wardrobe staples and fashion trends for women over 50 to help you look and feel your best at any age.

Little black dress

Wise calls the little black dress “one of the original wardrobe staples.” She adds that the little black dress is “perfect for women over 50” because it is easy to throw on and the styling opportunities are vast. Wise loves this Quzzion Silk Mini Dress.

“You can keep it casual with sneakers and a jean jacket or put a blazer over top with heels and it looks professional,” Wise says. “Pairing the dress with t-shirts, button-downs, and sweaters is another great way to give it a different look. It serves as the perfect base for outfit inspiration.”



ELLENWELL Essential Mock Neck Dress





Quzzion Silk Mini Dress

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GRECERELLE Short Sleeve Black Dress

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Stretch cotton pants

A reliable and versatile pair of comfortable pants is a great addition to any wardrobe. Stretch cotton pants can be worn “from work to weekends,” says Cassandra Sethi, personal stylist and founder of Next Level Wardrobe, who recommends this “polished” pair from Ralph Lauren. She adds that they are “perfect for the ladies whose weight fluctuates often,” as they have a loose-yet-flattering fit.

Try styling yours with a vest and heels for the office, or sneakers and a tucked-in t-shirt for more casual wear.



Sarin Mathews High Waisted Wide Leg Pants



Lauren Ralph Lauren Double Faced Stretch Cotton Ankle Pants





Dickies Relaxed Straight Stretch Twill Pants

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Crossbody bag

“It’s essential to have a carryall that isn’t just about style, but also function,” Conroy says. “You get to go out and about hands-free, as you run errands, jet off to work, stash snacks away for the grandkids (but make it chic), and everything else in between.”

Conroy shares the Rebecca Minkoff Darren Surplus Small Crossbody Bag as a prime example, and suggests styling it with espadrille platforms or flats and a Panama hat for a super-trendy “coastal vibe.”



The Drop Diana Top Handle Crossbody Bag



Rebecca Minkoff Darren Surplus Small Crossbody Bag



FashionPuzzle Small Triple Zip Crossbody Bag

High-quality jeans

While you don’t need a closet overflowing with jeans, Wise recommends finding two or three reliable pairs that you can rotate. “It’s worth investing in a high-quality pair of jeans because these are a fashion staple that you will wear over and over again,” she explains. “Jeans are the perfect go-to bottoms for women over 50 because they look good with just about everything.” Wise loves Madewell jeans for their durability and variety of sizes, styles, and washes.





Lee Mid Rise Boyfriend Jean

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Madewell The ’90s Creased High Waist Straight Leg Jeans



Levi’s Wedgie Straight Jeans

Striped button-down

A striped button-down is a “must-have” for your wardrobe, Sethi says. “Easy, breezy, and perfect for every occasion, you’ll get so many outfits out of this piece,” she adds. Sethi points to this Favorite Daughter Stripe Shirt at Nordstrom as an example, but the options are endless. Opt for thinner stripes, go more neutral with a black-and-white option, or try something bold with brighter colors.



AISEW Button Down Striped Long Sleeve Collared Blouse



Favorite Daughter The Doors Always Open Stripe Shirt



Fairy Season Striped Long Sleeve Button Down

Vest

“Sure you might be over 50, but you can still wear a vest for work or play,” says Conroy. Choose an option like this Cupio Scallop Detail Vest which is not only style-savvy but workwear-approved and super versatile.

Conroy suggests styling it with high-waisted trousers or matching shorts and a woven leather shoulder bag. Or, layer with a long-sleeve shirt underneath for more coverage.





Adrianna Papell Sleeveless Duster Vest

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Cupio Scallop Detail V Neck Vest



Norma Kamali Vest with Lapel

Reliable blazer

A well-fitting, stylish blazer is an absolute “wardrobe staple,” according to Wise. “This is a great layering piece for women over 50.” While oversized blazers are a bit more on-trend right now and offer a casual, laidback feel, a tailored one gives you a more put-together (and office-appropriate) look.

Wise suggests wearing a blazer to elevate your jeans or tossing one over a little black dress for a different style.





The Drop Blake Long Blazer

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Grlasen Casual Oversized Blazer





Cicy Bell Open Front Blazer

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Sneakers

You can’t go wrong with a great pair of cute-yet-comfortable sneakers, which Sethi says “are a must-have for every woman.” Sethi likes the adidas SL 72 OG Sneakers in particular. “You want to have a fun sneaker, which is cool to wear in the warmer months. You can pair them with jeans, shorts, or skirts—and it’s the perfect amount of pop for your outfit.” Try some of the best walking shoes or opt for ones that fit your needs (like the best shoes for flat feet or the best ones for plantar fasciitis).



Reebok Club C Sneaker

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adidas SL 72 OG Sneaker





Dr. Scholl’s Shoes Madison Platform Lace Up Sneaker

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White button-down

A great rule of thumb while shopping for new clothes is to opt for things that can work with what you already have in your closet. And if you don’t already have a quality white button-down shirt, it’s time to grab one. It’s “a great staple that can be styled a million ways,” Wise says. “This white button-down is perfect for women over 50 because it always gives an effortlessly chic look.”

Wise suggests tucking it into jeans and pairing it with ballet flats for a more polished look, tying it over your little black dress to transform it into a skirt, or using it as a swimsuit cover-up when you hit the pool or beach this summer.

Casual shirtdress

“It’s so easy to get stuck in the endless loop of pant and top combinations. Liberate your wardrobe by introducing a casual dress with some bite,” Conroy says. “Creating additional pattern and texture, a striped maxi shirtdress provides coverage without your outfit being boring and flat. Style with stacked cuff bracelets and gold stud earrings to complete the look.”



chouyatou Button-Down Shirt Dress



STAUD Joan Stripe Maxi Shirtdress



Amazon Essentials Georgette Long Sleeve Midi Length Shirt Dress

Conroy also suggests adding a denim version of the shirtdress (like her pick from Nordstrom) which is “understated but still offers maximum impact” and “allows you to bring femininity to your everyday style.” Pair yours with a block heel and colorful tote bag, and all eyes will be on you, Conroy says.





Kuraki Denim Button Front Maxi Shirt Dress

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Wash Lab Denim Weekend Belted Denim Shirtdress





Lee Legendary Western Denim Shirt Dress

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Flats

“Everybody needs a good pair of flats. Whether that be loafers or ballet flats—which are super in right now,” Wise says. She adds that the versatile nature of the shoe type makes them a necessity in your closet. They can be dressed up for the office or dressed down for running errands or a casual lunch date. For women over 50, Wise recommends searching for a quality pair to avoid feeling uncomfortable throughout the day.

Wise loves these butter-yellow Mary Jane’s for summer and these classic ballet flats from Dolce Vita. Try wearing yours with dresses, skirts, or jeans—and accessorizing with a matching bag and jewelry.



C.Paravano Mary Jane Shoes



Dolce Vita Reyes Ballet Flat





Steve Madden Belinda Mule

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Kitten heels

Not only are kitten heels on-trend and classically stylish, but they are also much more comfortable than their high-heeled counterparts. Kitten heels are “perfect for the woman on the go who wants not to have to change shoes,” Sethi says. This Stuart Weitzman kitten heel “would look great with skirts and trousers year-round.”





Guess Dista Heeled Sandal



Stuart Weitzman Tully Pointed Toe Slingback



Steve Madden Mod Mule

Open-knit sweater

Sethi points out that for women over 50 going through changes relating to menopause, it can be important to consider how things like body temperature will factor into your style. “You may need some items that breathe throughout the day,” Sethi explains. She recommends opting for breezy styles like an open-knit sweater, which is cool enough to wear on its own and can be layered underneath a blazer or over a tank top.





Dokotoo Crewneck Hollow Chunky Knit Pullover Sweater

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Sanctuary Open Knit Sweater



Ebifin Crochet Sweater

Wingtip derby shoes

“Sometimes it’s nice to take a break from sneakers and flats. Cue wingtip derby platforms,” Conroy says while sharing this stylish platform version from Cole Haan. “Allowing you to elevate your ensemble while still being sporty, they’re great with linen pants or jeans. It’s oh so Diane Keaton when styled with black dress pants, a crisp button-down, and menswear-inspired suspenders.”



SoftWalk Willet Wingtip Derby



Cole Haan ØriginalGrand Platform Wingtip Derby

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PIVAPAM Black and White Wingtip Chunky Heeled Shoes



Shannen Zitz is an Assistant Editor at Prevention, where she covers all things lifestyle, wellness, beauty, and relationships. Previously the Editorial Assistant at Prevention, she graduated from the State University of New York at Cortland with a bachelor’s degree in English. If she’s not reading or writing, you can probably find her frequenting the skincare and makeup forums on Reddit or hogging the squat rack at the gym.