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Miriam Shor as Diana Trout and Sutton Foster as Liza Miller in Younger.
Photo: TV Land

I Wish I Didn’t Care About Dressing My Age

But now that I'm in my 40s, I definitely do.

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I had avoided watching Younger until about two weeks ago, when I finally decided it was a pop culture moment I needed to understand. But I was wary and nervous in a way that doesn’t happen when I watch, say, Game of Thrones, a show that delights in beheading beloved characters and showing you poop montages. No, Younger was scarier for me. You see, a show about a fortysomething woman who tries to fit into a world of millennials hits a little too close to home — because it’s basically what I do.

The premise of the show is that Liza, a 40-year-old divorcée who has been out of the workforce to raise her daughter, can’t find a job in publishing, her old profession. After a hot millennial guy hits on her, she decides to pretend she’s 26 and gets a job as an assistant to Diana, a demanding fortysomething woman in the marketing department at a book publisher.

Because this is real life, that’s not exactly how my story goes. I made a career change seven years ago, when I was 38, from working as a nurse practitioner to writing about makeup on the internet. Most of my co-workers are 15 to 20 years younger than I am. Unlike Liza, however, I have never lied about my age. When I applied for the internship that jump-started my new career, it would have been incredibly awkward (and potentially illegal) to shave all that time off my professional life. Also I’m pretty sure I’ve always had to show my driver’s license to every employer I’ve ever had — they never really satisfactorily explain that on the show.

Diana, a fortysomething, dressing like a fortysomething.
Photo: TV Land
Liza, a fortysomething, dressing like a twentysomething.
Photo: TV Land

Anyway, I’ve made it through the first season and a half. The show is fine, but I find myself constantly analyzing and thinking about the wardrobes of two of the main characters.

What do you wear as a supposed 26-year-old (Liza) and fortysomething professional (Diana) in the eyes of a TV show, which is essentially a distorted lens for our broader society? The two women are very obviously juxtaposed in an exaggerated version of what “dressing your age” should look like. Diana’s penchant for statement jewelry and Liza’s mismatched prints and short skirts codify their roles and the (ostensible) generations to which they belong. This concept is solidified when Liza goes back to New Jersey to meet her old book club friends. To jump back into Gen X, she puts her hair up into a matronly French twist and throws on a cardigan and what can only be called “slacks.”

I’ve realized recently that shopping for your age is a continuum, which is why it was so jarring for me to see Liza generation-hop. You don’t suddenly just go from Forever 21 to Chico’s. When I hit my 30s, I felt like I had nailed my personal style. But recently, for the first time ever, I’ve started asking myself, “Is this age-appropriate?” when I go shopping. It’s not a comfortable feeling, because for the last 15 years I’ve felt really confident with my personal style and always operated under the assumption that you should wear what you feel good in.

The problem is that I’ve stopped feeling good in certain things. Dress lengths that used to be fine now seem too exposed. High heels now feel like a costume rather than the uniform they used to be for me. I used to love trashed and ripped-up jeans, but now when I wear a pair I think, “Cheryl, do you really need to show off your kneecaps in this manner?” I’m constantly wondering if my choices are ridiculous.

The thing is, I have very few resources to turn to for an answer to this question. There are my friends, of course, but a lot of them are just as confused as I am. We went out for drinks recently and had a half-hour conversation about hemlines. Nothing was resolved. I love Girls of a Certain Age, the blog run by Kim France, the founding editor of Lucky magazine, but her taste is a little more boho than mine. Otherwise it’s pretty grim out there. And moving along this age/clothing continuum makes shopping hard. I used to love Shopbop, but nothing feels quite right anymore and I haven’t ordered from there in over a year. Ditto Zara. I don’t know the difference between Revolve and Reformation. Urban Outfitters may as well be Gymboree for as much as the clothes there speak to me. I shop frequently now at COS for weird architectural shirt dresses and at Athleta for oversized button-down shirts. I’m lucky to occasionally be able to afford to shop at Barneys and Net-a-Porter, usually for shoes or bags. Otherwise, I’m in a rut.

The online lifestyle media features a lot of stories with headlines like “The 5 Pieces You Need in Your Closet Before You Turn 30.” I have things in my closet that are surely older than the person who wrote that article. I don’t need someone telling me what to wear. I just need commiseration. I’d like to see an article exploring something like “Yeah, We Aren’t Really Sure About That Cutout Either.” But I get it. Millennials are the biggest living generation now, according to the Pew Research Center. Their problems are going to take up more bandwidth than those of a lady who can’t decide whether or not wearing her old New Order T-shirt is cool or sad.

I’m definitely inspired by some of the things my younger co-workers wear. Or maybe “influenced” is a better word; I don’t think I’m always fully conscious of it. It’s because of them that I pared down my jewelry and gave up some statement necklaces circa J.Crew 2005. I’ve embraced simple, well-tailored jumpsuits after initially being scared of them. I’ve learned how versatile a bodysuit can be. (But I also know that someday these young women will look back at their mom jeans and say, “I cannot fucking believe we wore those.” I know this is going to happen because it’s what I say now — I wore them in the ’80s and early ’90s, when they were just called “jeans.”)

I’ve started following older women to see how they’re moving along their own style continuums rather than wallowing in thoughts of “Gah, I’m too old to wear that!” every time some image of a starlet in a romper invades my social media feeds. I stalk any coverage I can find of French first lady Brigitte Macron, 64, whose closet I would plunder in a second. Celine Dion, who is only a few years older than me yet seems decades wiser, has plunged headfirst into wacky couture, and it is glorious. Beauty entrepreneur Linda Rodin, sixtysomething and never without her signature lipstick, is cool elegance personified.

I kind of hate that I’m judging my clothing choices as they relate to my age and don’t want to succumb to what my head knows is just insidious societal pressure. But I don’t want to dress like a 26-year-old either. Being that age sucks in a lot of ways. I worked really hard for the knowledge and experience I have. What conveys that without looking, you know, old? And also without looking like I’m trying to be young? Since you all know how old I am, I’m just going to go ahead and date myself further here, but I finally understand the Kathy Bates line in one of my favorite movies, 1991’s Fried Green Tomatoes: “I’m too young to be old and I’m too old to be young.” I saw some good advice written recently in — of all places — the Wall Street Journal for — of all people — fortysomething men: “Only old people are told they look young, and it is usually when their strategy is showing. Shoot for looking good, not young.”

I don’t know what the current season of Younger holds and I’m not sure I’m actually going to commit to the whole series, but presumably Liza hasn’t come out to everyone in her life about her real age yet or the show would be over. If (or when) it happens, I hope she keeps her millennial wardrobe to mix in with her cardigans.

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