Finding Your Stride So You Can Strut

With the regrettable resurgence of 90s styles flooding our stores with neon crop tops and platform shoes, hip padding and oversized sleeves (or ugh, those floral Little House on the Prairie dresses!) you might be feeling like fashion just isn’t your thing anymore. I mean, you’re over 50. You’re probably asking yourself: Who’s looking at me, anyway? Where am I going that people will care what I’m wearing?

But we’re here to argue — loudly, vociferously, vehemently: That’s the wrong attitude. 

Because, in truth, being over 50 makes now the time to embrace any sartorial sense you’ve ever had and maximize it. Put it in bold. Not necessarily literally (not everyone can carry off accessories like Prue Leith), but figuratively. If you have always admired a preppy, yacht-club aesthetic, then lean into Ralph Lauren so hard he’d fall over. Or, if you prefer, you could go the opposite direction and swathe yourself in flowy, earthen-hued fabrics and embrace your inner flower child. (We don’t mean to describe Jane Fonda and Lily Tomlin’s characters from Grace and Frankie, but you get the gist.) The idea is, if it’s true that “no one is looking at you,” then you should feel free to be yourself. You’ve been granted a free pass to take risks and try new things. And here’s the kicker: You’ll feel great. You have to admit, as women, we feel better about ourselves when we look good. But looking good takes a bit of intention (and maybe even a little more effort than it used to).

You are worth making that effort. Here’s how.

Woman shopping for a bra - getting the right fit over 50

First Priority: Fit

Whatever look you’re going for, the most important thing to get right is the fit. When something doesn’t fit it draws the eye immediately, and that rarely ever flatters your figure or helps you make a statement. (Well, it’s a statement, to be sure, but probably not the one you want to make.) 

By this point in your life, you probably have a good sense of when things are too small or ill-fitting, but you might be overlooking one of the basics: your undergarments. Yes, ladies, if you haven’t been properly measured for a bra recently, it’s time. Go to a frou-frou lingerie shop where everything is in French and the sales ladies give you the side-eye. Or if that’s too intimidating, department stores like Nordstrom will usually have specialists that actually know what they’re doing. But make sure that wherever you go, someone whips out a fashion tape ruler and measures you properly, and then checks to make sure that the bra you’re buying fits you. (Vogue also has great tips on bra fits.) 

“But people don’t ever see my bra!” you’re protesting. Yes, but wearing the correct bra size will help you feel more comfortable, help your clothes fit properly and give you a boost — both literally and figuratively.

Woman wearing jeans, relaxed and comfortable
Image by Ekaterina Demidova, via

Second Priority: Comfort

My mom used to jokingly chide, “pain is beauty, and beauty is pain” as I howled whenever she tried to brush my unruly hair. It often pops into my head when I contemplate wearing a pair of jeans that are just a tad too tight, or heels that I know will give me aching feet within minutes. But as I’ve gotten older, I’ve learned the crucial lesson that I can actually look great without being uncomfortable and that, in fact, I look better when I feel the part. And with all those years under my belt, I’ve gradually learned the styles that fit my body, rather than the other way around. 

It helps to build outfits around something that you know fits you. Spend the time to find the right pair of jeans, for example. Once you have a pair that are flattering and comfortable, don’t sag in the wrong places or pinch in others, you can pair them with just about anything. (Shout out to Democracy jeans. I cannot tell enough people about them — they’re comfortable, hold their shape and come in a million variations.)

Here’s another secret to comfortable fashion: Try not to buy anything that requires shapewear underneath, unless it’s for a formal occasion. Shapewear was designed by the Devil, who is clearly a man. It is restrictive, it doesn’t breathe, and if it flattens one area it often causes rolls and bulges somewhere else. If your clothing fits properly, you don’t need shapewear. 

Finally: Strut Your Stuff

Fashion has rules, yes. But many of the rules were made for 20-somethings who still desperately want to fit in. You’re past that. Now that you’re over 50, you can wear whatever you want as long as it fits well, feels great and you wear it with confidence. You want to wear quirky hats and scarves, à la Diane Keaton? Go for it. Accessories are a great way to style an otherwise drab outfit and they will draw the eye away from problem areas. Pair unexpected items. Mix prints. Wear bright colors. Define your waist, even if it isn’t as slim as it used to be. And if you need inspiration, check out these over-50 fashion influencers: Cindy Hattersley, Grece Ghanem, Iris Apfel, Luisa Dunn and Lyn Slater.

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