Years ago, I appointed a reverse mentor, a friend 15 years my junior that I can ask technical and sometimes pop culture questions. She’s the one who will explain (and promise not to laugh) trends or define words/expressions I’ve never heard of like text abbreviations (FAFO? SMH?) or share why dip manicures are life-changing.
She recently asked me if I knew how to wear my socks.
“What now?” I asked. I mean, I feel like I’m OK in the sock department. I have socks I like to wear to work out (Balegas fit perfectly and don’t slip down), I have socks I like to wear under boots (thin trouser socks), and sometimes, prompted partly by the fact that this was said to be the fashion preference a few years ago, I go without.
“You’re supposed to let them show,” she said. “Above the ankle. All my 20-something pals say so.”
Who knew? I’m definitely not on trend. A decade or so ago I finally embraced skinny jeans after decades of wearing less flattering relaxed styles because I thought skinny jeans were for super skinny people. They’re not. They’re fitted and look good on many body types. Then, maybe two years ago I heard they were out of style. I kept mine, which is cool because now I hear they’re making a comeback.
Who can keep up? Maybe, we can't, which may be a good thing as we get older, and our style evolves.
My dear grandmother dressed exactly like a storybook version of a grandma. Housecoat-type dresses that hit just below her knee. Low-heeled, sturdy black shoes and thick stockings. A shawl or a cropped sweater she called a “hug-me-tight” across her shoulders. To me, she was the coolest. But I can’t imagine dressing that way. And I don’t plan to. But what is the right approach?
It’s a post-Covid, much more casual world but I don’t want to look like I just rolled out of bed when I leave the house. I want to be comfortable but not frumpy. At the same time, I want my clothes to be flattering but not tight or constricting.
So now what?
We’ve all heard the fashion “rules” when it comes to how you’re supposed to dress when you reach a certain age. No miniskirts. Cover your arms. Don’t bare your midriff. But it seems there are plenty of women flouting these rules. Have you seen Baddie Winkle, the 90-something Instagram star who wears bikinis, shorts, corsets, and mini dresses in every outrageous sparkly combination and color? Not quite my style but I find it completely delightful.
Good news: there are more choices than there were in my Gram’s day. You can shop online and get inspiration from Diane Keaton, Michelle Yeoh, Helen Mirren or Angela Bassett. These are women who not only look good for their age (kinda hate that expression), they look good period. How do I do that?
The truth is, I don’t want to look old. I don’t want to just give up and wear nothing but caftans. (Although, there are some pretty ones.) But if I feel self-conscious or like I’m trying too hard or wear something that’s just off, that defeats the purpose. I’ve pretty much ditched high heels, minus the occasional wedge or kitten heel, but there are so many cool low-heeled booties and sneakers and flats.
Maybe the key is simply being true to yourself. I want to look like a rock star (check out 79-year-old Debbie Harry’s Wildfang capsule pieces) without looking ridiculous. But I don’t want to wear things because I should (because I’m trying to be cool) or shouldn’t (because society says not to).
My co-host and I recently interviewed style guru Stacy London for an episode of our Let’s Talk Ladies podcast. She recently debuted her byStacy London clothing line on QVC as one of the channel’s Q50 Ambassadors (accomplished 50+ women), so we thought she’d be the perfect person to ask if there’s such a thing as dressing your age.
“Yes, you should dress your age,” she told us, “depending on what that means to you personally. And the reason I think that age plays into our style is that like everything else in our life we evolve and what you liked in your 20s may not be what you like in your 50s.”
Makes sense for someone who made her initial splash on a makeover show called, What Not to Wear, and recently re-tooled her concept in the new show, Wear Whatever the F You Want.
As Prince once sang, “Act your age, not your shoe size…” But remember, you’re never too old to wear Mary Janes. If you want to.
This essay was inspired by the Let’s Talk Ladies podcast episode, Dress Your Age, on Spotify and Apple. Our new season is available on YouTube. We’d love for you to listen!