7 Clothing Items Women Over 40 Wear That Are Aging Them

As elder millennials are officially in their 40s — gasp! — it's time to take a look at what they're wearing. Like any other generation, millennials can fall into a fashion rut, meaning they continue to wear what worked for them when they were younger, despite the fact that some of those looks are woefully outdated. It's a fairly common thing for every generation. People of all age brackets tend to struggle to give up looks from the past, especially their favorite trends.

While there's nothing wrong with hanging on to things you wore in your 20s and 30s, the reality is that certain items can really age you once you get to 40 and older. Because of this, being aware of what's trending and equally, what isn't is important. The good news is, in addition to there being plenty of stunning jewelry trends for women over 40, there are also clothing looks tailor made for mature folks. You can be just as en vogue in your 40s as you ever were. But you can't get there until you open your mind to letting somethings go.

"I always think you should wear what makes you feel amazing. But since I work with a lot of women in their 40s and up, I've noticed some re-occurring patterns with a few pieces and unfortunately, they tend to add years and age your look," San Diego personal stylist and image consultant, Cynthia Kennedy of Your Style Transformation Academy, exclusively tells Women. "My clients are always relieved and pleasantly surprised once we swap them out for more modern and fresher options."

As Cynthia Kennedy is quick to point out, big and boxy cardigans may be cozy and comfy, but they lack shape, which can be problematic for people of all sizes. "These long, bulky cardigans can drown your frame and swallow you up," Kennedy exclusively tells Women.com. This can cause you to look unintentionally frumpy. Because of this, you want to downsize on the big sweaters and opt for ones with more structure. According to Kennedy, she had a client who finally threw in the towel on her favorite waterfall cardigan and it really elevated her look. "She instantly looked taller, sharper, and more youthful," says Kennedy. In other words, leave your go-to cozy cardigan for home-only wear.

Although low-rise jeans made a quick comeback in summer 2023 and were surprisingly wearable, it was a short-lived trend. Why? Probably because people once again realized it's just not a good look on anyone — no matter the status of your abs. Combine a low-rise waist with a bootcut one and yikes! You've pretty much just announced the year you were born — not that there's any shame in aging, of course. While there's no need to try and keep up with Gen Z's trends (looking at you, barrel jeans), your best bit is to opt for a jean with a timeless fit. "If you want an easy and chic look, go for straight-leg jeans in a clean, dark wash," Cynthia Kennedy exclusively tells Women, explaining that such a cut won't just update your whole outfit, but will be far more flattering no matter your shape.

Unless you're competing with Karoline Leavitt for the frumpiest work outfits, you may want to reconsider wearing extra long midi skirts. "Those mid-calf, shapeless skirts in stiff fabrics can look frumpy and dowdy really fast," says Cynthia Kennedy, who explains that skirts that move, like those made of silk, organza, wool, or lace, are your best bet. A skirt that's at the knee, but is a fit-and-flare will breathe some major new life into your skirt game. "You'll still get the coverage you want, but the look will be sophisticated and modern," says Kennedy.

While the rise of 'ugly shoes' proved that some are in an era of not caring what others think, the reality is that comfortable shoes don't have to be ugly. In fact — and hold on to your seats! — shoes can be more than one thing. "I understand that comfort is important, but clunky shoes can really ruin an outfit," Cynthia Kennedy says of heavy, orthopedic-like shoes. According to Kennedy, when she has a client who values comfort over style, she suggests loafers, block heels, or sneakers — all of which are chic in their own way. "They're not only structured and supportive, but stylish and modern," says Kennedy, adding that you shouldn't have to choose between being comfy or fashionable.

As we saw in early 2025, boho chic, a previously outdated trend, came back with a vengeance and it's still here. But as Cynthia Kennedy explains, if you're not careful with this trend and let yourself lean into too many frills and ruffles, it can look like more like a costume and less like a legit look. Case in point: Seinfeld's puffy shirt. "You can still get that romantic feel with tops that are a little more sleek and polished," says Kennedy, who suggests a lavallière-collar or the iconic pussy bow blouse. "[Or] asymmetrical cuts with unique necklines and draping, or wrap tops that feel easy, elegant, and effortless," says Kennedy.

If you're over 40, there's a pretty good chance you still have one of those huge purses from the early 2000s. Like the Olsen twins and their extra-large Balenciaga bags, many embraced the trend because you could literally dump everything into them. While practical, it not only looks dated, but it's simply too much bag. If you don't want to age yourself or look like you're still swimming in Y2K waters, Cynthia Kennedy advises switching out the big bags for bucket bags, totes with the timeless structure top handle that your wardrobe needs, or crossbody bags. "[They'll] instantly elevate your outfit without sacrificing space and function," says Kennedy.

Remember the early 2000s when if you didn't rock the low-rise, bootcut denim, you probably wore jeans with too much whiskering or, even worse, ones that were bedazzled with rhinestones? While it may be hard to remember why anyone thought this was a good look, they are details that need be ditched stat if you don't want to advertise your age. "[These] are styles that are basically stuck in the past and will show your age in no time," says Cynthia Kennedy. In fact, no matter what pieces you have — jackets, blouses, socks, literally anything that is bedazzled in any way — toss them. If this trend comes back, you can easily bedazzle your entire wardrobe again, but here's hoping it all stays in 2003 where it belongs.