How our sense of style evolves with age
While midlife brings some challenges to getting dressed and buying clothes — such as pants that are too tight around the waist and blouses that suddenly look frumpy instead of retro — one silver lining is that they’re balanced out by a greater sense of confidence in our sense of style. Back in 2022, the Internet had a field day analyzing, criticizing, and sometimes loving the “chaotic outfits” sported by Portia, the hapless personal assistant to Jennifer Coolidge’s Tanya McQuoid on the second season of The White Lotus. I suspect that much of the obsession with her bizarro lewks — some of which look like they were thrown together from random items from the Urban Outfitters sale rack — was because so many of us could relate.
Who doesn’t look back and cringe at some of our ensembles from our early 20s, when slipping on a new persona (Deadhead, punk, preppy) was as easy as changing clothes. I recall flirting with some kind of goth-hippie look, sporting a long black skirt with a fringe on the bottom paired with a wide fabric headband worn low over my forehead — which prompted a sorority sister to refer to me as “Rhoda” of The Mary Tyler Moore Show fame.
If we spent our 20s and 30s (and even earlier years, sadly) constantly feeling self-conscious about how we looked, the 40s and beyond is when we start not to care what anyone else thinks. The world says I’m too fat to wear leggings? Too bad! Should I not wear a bikini because of my meno belly? Who cares! Have you seen what most middle-aged men at the beach look like?
Women in midlife dress to please themselves
It’s often said that women dress for other women, not men. But as we get older, we increasingly dress mainly to please ourselves. We may decide some things are no longer flattering or not right for our body shape, but that’s a decision based on what makes us feel good about how we look, not a diktat from the fashion gods. The old rules about propriety and “dressing your age” no longer apply. The idea that women shouldn’t wear miniskirts or wear sleeveless tops after 40 or 50 has gone the way of ladies’ white gloves.
We’re also free from feeling we have to abide by trends — especially since we’ve seen the ones from our youth come around again (and again). I still have not gotten over the reappearance of acid-washed denim, a fad that was best left in the ‘80s. Some emerging trends may have us scratching our heads (the no-pants look, anyone?), but we can take them or leave them. When skinny jeans were deemed “out ” by Gen Z, millennial and Gen X women collectively shrugged our shoulders and kept them in rotation.
We’re also no longer willing to suffer for the sake of fashion. Heels are now often reserved only for very special occasions, if worn at all. I love the look of very high-waisted jeans, but not being able to breathe when I sit down is a problem. Anything too restrictive is a no-go. That doesn’t mean we have to give in entirely to athleisure, but we’re choosing clothes that work with our lifestyle, whether that’s a pair of leggings so we can bike to the store or a skirt that we aren’t dying to immediately take off after a long work day.
All this makes us more likely to invest in high-quality clothes — and often, after a couple of decades of working, we finally have the budget to do so. Instead of building up a wardrobe, we’re curating what we’ve got, creating new combinations with what we have, and carefully selecting new items to complement our closets. Plus, old trends becoming new again works in our favor — how many of you pulled out a vintage pair of Doc Martens to take advantage of the combat boot trend?
And just because we’re not young anymore doesn’t mean we can’t still have fun with clothes. I hugely admire women with an eccentric signature style that becomes their calling card — like the late Iris Apfel, the beloved icon known for her round glasses, ropes of bold necklaces, and giant bangles. But not everyone wants to make that kind of commitment. Instead, we can adapt styles we like. I was recently inspired by Juliette Binoche as Coco Chanel in the TV series The New Look to break out my pearls and fasten a black ribbon on top of my head. Another day, I went boho-western in a denim shirt, a couple of gold necklaces, and cargo pants. When I don’t have a lot of time or energy to spend on getting dressed, I might throw on a striped shirt, jeans, and a jacket for a quick dose of casual French chic.
Part of Portia’s fashion problem was that she never really owns what she is wearing. Compare her to her boss, the hapless Tanya McQuoid, played by the wonderful Jennifer Coolidge. Tanya is supposed to be a bit much, and her outfits reflect that: the body-hugging, boob-enhancing floral-print dresses, the La Dolce Vita head scarves, even a mantilla. But girl, she rocks those looks. You don’t question what she’s wearing because she sports them with the blithe assurance of the rich — even if she’s a neurotic mess in other areas of her life.
And that’s what it all comes down to, really. I’ve always said you could wear a ball gown to a breakfast meeting as long as you have enough confidence — and midlife is when many of us finally do.
