Women Over 50 Are Rewriting the Rules of Fashion for Themselves

Women are ‘leading by example’

But fashion isn’t just coming from brands — it’s coming from women themselves. Brittany Hennessy, an author, influencer strategist and cofounder of Carbon August, a brand that helps brands with an influencer marketing strategy, said women over 50 are increasingly leading by example. “It’s long overdue,” she said. “They have wardrobes to die for, the disposable income to back it up, and now they’re finally being seen — and celebrated.”

Hennessy cited bold, expressive brands like Farm Rio, with its vibrant prints and flattering shapes that work across ages. “You’d think it’s for younger people, but all ages wear it, and everybody looks great in it,” she said. For women who live in elevated athleisure, the brand Varley delivers on both comfort and chic. “They make these gorgeous athleisure sets in really thick cotton — super flattering,” said Hennessy. And for those who lean luxe, The Row remains the gold standard. “They don’t do too much, but it’s clean, elegant and ageless.”

Find a look and stick with it

No matter the brand, looking great over 50 often starts with knowing what works — and what doesn’t. For many women, tailoring is an unsung hero. “If you find a great basic, a little tailoring can turn it into something you’ll wear again and again,” said Cantrell. Hemming pants, adjusting sleeves or reshaping a neckline can take an item from “meh” to magic. Hennessy agreed that the smartest style decisions don’t always involve buying more. “Where you get in trouble are those things that are neither a statement nor a staple,” she said. “You wear it and know it’s not right, and that affects your confidence. That’s when tailoring or rethinking the piece is key.”

FIT panelist Teri Agins, a veteran fashion journalist, echoed that less really can be more, especially when it’s well edited. “Go in your closet, see what looks good on you — that’s your look. Then stay in that lane,” she advised. “If wrap dresses work for you, great. Try a new color. But don’t feel pressure to reinvent your silhouette every season.”

One approach Agins swears by is to take selfies in different outfits from multiple angles. “Some of the stuff you thought was cute isn’t as cute as you think,” she said. “Seeing yourself in photos helps you build a wardrobe that works in real life, not just in the mirror.”

And while you’re at it, Agins says to invest in an old-school fashion tool that never lies: a three-way mirror. Unlike a single front-facing mirror, a three-way reveals how your clothes look from the back and the sides, areas many of us forget to check. “A three-way mirror shows you the full picture,” Agins said. “Your outfit might look fine from the front, but if it clings, gaps or bunches in the back, you’re not going to feel confident wearing it.” Combined with a few well-lit selfies, it’s one of the easiest ways to develop an eye for what truly fits and flatters.

As for what you wear on a daily basis, Hennessy is a fan of creating a uniform. “If I find a shirt and pants I like, I’ll buy them in every single color. It saves time, and I always feel pulled together.” For her, a two-piece set like this and a great pair of sneakers are the ultimate confidence combo.

Agins emphasized not skipping the basics — literally. One of the most overlooked upgrades: a better bra. “Your rib cage expands in your 50s — sometimes by as much as three inches,” she said. “I thought I was a 34B forever. Turns out I’m a 36C. And that makes all the difference in how clothes fit.” A properly fitted bra, she said, can transform how everything in your closet looks and feels. She recommends trusted lingerie stores that specialize in bras, or working with a specialist at Nordstrom or Saks.

Shop online, strategically

Of course, finding great pieces today increasingly means shopping online. And while it’s convenient, Agins says it requires a little strategy. “Don’t shop on your phone — the screen’s too small. Use a laptop so you can really see the details,” she advised. “Pay attention to armholes, hemlines, model height — it all affects how something will fit you.”

Agins also suggests sticking with retailers that offer free round-trip shipping so you can try items risk-free and return what doesn’t work. Not sure where to start? Virtual personal stylists — offered free through retailers such as Nordstrom and Macy’s — can help you plan outfits around what’s already in your closet.

If you’d rather opt out of buying new and potentially adding to landfills, check out vintage and secondhand clothing. Not only is resale a more sustainable way to shop, it can also be a gold mine for discovering unique pieces, elevated fabrics and long-lasting construction that often surpasses what’s on today’s racks. Agins is a longtime fan of ThredUp, describing it as “like eBay for clothes except easier to use, with a single, trustworthy retailer behind it.” The site offers thousands of gently used pieces, many from brands you’ve never heard of but may want to know.

Agins also recommends shopping resale through platforms like The RealReal or Poshmark, especially for higher-end pieces where you want quality but don’t want to pay full retail. The key, she said, is to experiment. “This is trial and error,” she noted. “You need the freedom to try things, return what doesn’t work and get comfortable with how these platforms operate.” Bonus points if the site offers free returns, and triple points if you use resale to try out a brand or silhouette you’re curious about without committing to the full price. It’s not just thrifting, it’s smart, intentional wardrobe-building.

One final, unexpected tip: Embrace stretch, and skip the dryer. “Stretch makes everything more forgiving,” Agins said. “But don’t put anything stretchy in the dryer. Line-dry everything — your clothes will last longer and fit better.”

In the end, the panelist agreed, smart style over 50 isn’t about rules, it’s about refinement. It’s not about dressing younger, it’s about dressing better. And it’s not about starting over, it’s about building on what you already know to be true: your style, your shape, your confidence and your standards.