The late, great New York Times fashion and society photographer Bill Cunningham once said, “Fashion is the armor to survive the reality of everyday life.”  Whether you are 23 or 83, determining what to wear and how you want to present yourself to the world requires self-reflection and self-confidence. Whether you can then go out in the world and accomplish what you hope to, and whether the rest of the world sees you as you’d like them to, is another story, however. Especially for older women, who may be subject to not only ageism but sexism, being seen and valued as contributing members of society is always a bit of a challenge. But there does seem to be some progress, at least in the representation of stylish older women on the runways and in marketing campaigns. How that translates for the average older woman is what’s not clear.

On the runways and in magazine spreads (along with social media accounts) there are now usually one or two older women to be found. In fact, Vogue Czechoslovakia recently pictured the oldest model ever featured on a Vogue cover, 91-year-old Carmen Dell’Orefice. With her smoothed-over face and skin, she of course bears little resemblance to a typical 91-year-old (is there such a thing?), and, in fact, Ms. Dell’Orefice has been a professional model since she was 15 years old (the first time she was on the cover of Vogue). There are some designers that genuinely seem to welcome the representation of older women in the fashion world. As designer Rachel Comey commented, “We design for people at all stages and moments in their lives.”  However, the average age of runway fashion models continues to be 23 years old and even those who model at older ages tend not to “look” their age, with instead “willowy bodies and streaming locks” that few older women can replicate in reality. So it’s a mixed message being sent to older women trying to be stylish.

There are now modeling agencies that appear to represent a wider, more diverse (including age-diverse) group of models. For example, the stylish Accidental Icon Lynn Slater and her partner Calvin are now represented by an agency known as 11:14. There is another modeling agency that is getting some traction with more “real” looking older models. Called Celebrate The Gray (we first mentioned them back in 2019) they represent over 150 “real” models (along with older, stylish influencers) and they’ve worked with companies such as H&M and Athleta to ensure that marketing campaigns include images of older women that “real” women can relate to. So this is progress.

Yet, the reality is that “real” women still struggle to find comfortable clothing (as one expert makes clear, “If you’re not comfortable, you won’t be stylish”), and ensure they are presenting a vital, confident, and valued image. At the same time, no one wants to be told what to wear. In today’s world, it’s ever more confusing given the competing images and suggestions from the internet versus stores, social media, sustainability concerns, second-hand options versus rental opportunities, and fashion “experts” who tell you to wear whatever you want and then proceed to enumerate all sorts of options that most older women wouldn’t dare to wear. Leather pants?  Leather shirts? Who knows what’s right versus wrong when it comes to fashion these days? But as designer Marielle Wyse, owner of Wyse London says, “I just call it “clever dressing”- enhancing your best bits and covering up your not-so-great bits. That’s something that should happen at any age.” Enhancing your “best bits”- in fashion and in life- sounds like a good strategy for aging in style no matter what you choose to wear!