We absolutely do not buy into the idea that there are hard-and-fast rules that women in their 50s have to follow regarding their wardrobe choices. You will not see, “no short skirts!” or “no cleavage!” or “no distressed denim!” among our advice about dressing in one’s 50s. You, and you alone, are the world’s leading authority on what makes you feel confident, happy, and comfortable. We embrace that and hope you do, too! That said, there are some tips and tricks that can help you move your personal style into your fifties. Twenty-year-old women and fifty-year-old women are not the same creatures at all, thank goodness, and we want to help you use that experience, maturity, and establishment to lean into your taste and style in a way that expresses the fact that you have arrived.
Gone are the days of going into your local fast-fashion emporium and picking up T-shirts at four for $20. Mature women deserve better basics! Don’t get me wrong—I own plenty of $5 T-shirts because painting and gardening and power washing the garage must be done. At the same time, I understand that when going out in public, a well-cut T-shirt made of high-quality material and constructed to last looks better and more appropriate on a woman of my age and physique. I make sure the basics I wear are among the best pieces of my wardrobe.
Better basics—those featuring natural fiber fabrics, flattering cuts, quality construction, and thoughtful details—improve your whole wardrobe. The old adage, “Buy less, buy better, make it last,” is important financially and ecologically, but consider that it makes your wardrobe flexible, great-looking, and wisely curated. You earned the wisdom you have, so show it off. By this point in your life, you understand what cuts and washes of jeans look the best on your frame and figure, so stick with that but move up a level in quality. Superstores and big-box retailers are a fine place to pick up batteries and socks, but for your clothing, make considered purchases at reputable retailers. An acrylic sweater lasts for one or two seasons at best. A cashmere sweater can last a lifetime with proper care. A mature woman of style and taste knows which is the better addition to her wardrobe.
Fit is everything. Even women with terrific figures can use the odd nip or tuck—in their clothing! It is true that some pieces may need tailoring simply to fit properly; a skirt that bunches up at the waist or sleeves that hang to your knuckles are sloppy and must be fixed. However, a talented tailor can take almost any garment from good to sensational. For example, I once took a cocktail dress to my own tailor believing the straps needed to be shortened, but my brilliant tailor said, “That dress is too big.” In less than five minutes, she had pinned it in several places. I was surprised, but when I wore the altered dress to the event I had bought it for, I received a dozen compliments and was even asked if I had had the dress made! When an off-the-rack piece looks like it was made for you, you have the best of all worlds, sartorially speaking. Bespoke clothing can be prohibitively expensive, while the services of even a top-tier tailor are generally affordable.
If you don’t have a great tailor, find one. Ask your friends for recommendations, or take your pants to a local tailor rather than the dry-cleaners to be hemmed. If you like their work, you can take something else and see how that goes. When your clothing fits beautifully, it shows that you have attained taste and elegance commensurate with your maturity. Embrace it, because you deserve it.
If you care about fashion trends and fun fads, explore them through accessories rather than full garments. An animal-print bag, a neon scarf, or a fringe earring are the ideal way to try a short-lived trend. Dip your toes, proverbially speaking, into fads rather than doing a cannonball. Your high-quality basics can class up a fast-fashion scarf or belt, and the high-low mix will keep your looks fresh and interesting. If, as we are seeing with animal print, the trend has a lot of staying power, then you can move on to adding a good leopard-print shoe or skirt to your wardrobe. Some trends do stick and become classic pieces; think capri pants or pencil skirts.
If you simply must try a trend, make sure it can be altered later. Many years ago I fell in love with a high-end dress that had witchy pointed bell sleeves that were extremely popular at the time. After a couple of years, those sleeves were depressingly dated, so I had my tailor hem the sleeves to plain ¾ length. That dress is 20 years old and still looks amazing, thanks to losing the dated detail.
As a woman in your fifties, you may be at a very special time of life where you occasionally get very, very hot. Our best advice is to stock your wardrobe with tank tops, camis, and silk shells. These are cooler under your blazers or cardigans than a typical sweater or button-up, and if you are desperately uncomfortable you can easily remove your top layer. The key to this type of layering is to make sure your first piece is presentable; you can’t buy a three-pack of men’s tank undershirts like you may have in college! Look for smooth, well-cut tanks, camisoles that are sturdy rather than diaphanous, and genuine silk shells, because polyester doesn’t breathe.
One of the saddest things I ever read is that as we age, humans naturally lose the fat pad on the ball of the foot, making high-heeled shoes increasingly uncomfortable. If you love shoes the way that I love shoes, realizing that everyone ages out of five-inch heels and punishingly strappy sandals might be a blow to the ego, but it also explains a lot. I was frustrated at not being up to wearing my favorite shoes all night and wondered why going out dancing had become so unappealing, but it wasn’t me, personally, it’s just a part of life.
It turns out that many things are, and we can move our style into our 50s with accommodations for all the natural changes we go through. Are your fingers always cold? Step up your gloves to cashmere-lined leather. Is your skin more sensitive? Switch to natural, breathable fabrics wherever possible. Do your feet hurt? Ditch four-and-five-inch heels for kitten heels and supportive wedge heels. Check out super-stylish flats, smoking slippers, and loafers—it’s all of the style with none of the pain.
Maybe you have even begun to feel that you have put in your time and simply deserve to be as comfortable as you want to be, all the time. Perhaps you have decided that suffering for beauty is simply in your review mirror. Look into stylish knitwear, which has come a long, long way since our mother’s days of polyester double-knit. Almost every style of garment is available with an elastic waist these days, so you don’t have to live with the pinch-points. Consider dresses, many of which are as comfortable as nighties but keep you looking professional and pulled-together. You deserve to look your best as well as feel your best.
More than anything else, know that we support you in bringing your style into your fifties (and beyond!). If you have always leaned toward Preppy classics, it’s easy because being tidy and tailored was already a hallmark of your style, but if you have always been a little bit rock’n’roll, love the bohemian vibe. or live an active lifestyle that demands athletic wear, keep doing you! You can make small tweaks and adjustments to make your taste and style work at any age or stage of life. With a little thought and a little planning, your clothing will continue to help you be you.