What Does It Mean to "Dress Your Age"? `
Trying on clothes at Eileen Fisher; my ambivalence toward dressing "grown-up"; and challenging old assumptions. PLUS an open thread where you can chime in on your "age-appropriate" (or not) style.
Readers,
As I’ve mentioned ninety-million times in recent years, I’m freaking out about turning 60 in October. It’s causing me anxiety on multiple fronts even though, given what I’ve learned from working on this magazine, I should know better.
The front I’ll tackle today: Style, and my conflicted feelings around “dressing my age.” I touched on this a little bit in an earlier post, about buying a linen suit to wear when I had my picture taken as part of a “40 Over 40” photography show:
Not long ago, somewhere on the internet there was a wonderfully irreverent post about what an older woman should wear for certain types of occasions. The answer in every instance was: Whatever the fuck she wants. (If you have a link to that post, which now eludes me, please share it in the comments.)
I think about that post a lot these days, because I harbor this notion that once I turn 60, I’m supposed to start dressing like A Real Grownup Lady™. Like, it’s my duty to adopt a more formal look—smart skirt suits, crisp blouses, gabardine slacks, tea-length dresses—but also loose, shapeless linen outfits in muted tones that don’t call attention to the ever-increasing softness of my body and the changes in my shape.
This is hardly the first time such a notion has intruded upon my consciousness. And it bears mentioning that in the late 80s I worked at my grandfather’s women’s sportswear company, which made…smart skirt suits, crisp blouses, gabardine slacks. In any case, this notion has shown up around nearly every major milestone, plus every occasion for which I’ve needed to dress up. And each time I try to clothe myself like A Real Grownup Lady™, I suffer an identity crisis. I just don’t feel like me.
This made me want to ask all of you about the style adjustments you’ve made as you’ve gotten older, and the societal norms that have influenced them. In the comments please tell us…
How old are you? What’s your gender? Do you have a signature style you’ve always adhered to? Or have you deliberately changed your personal style at points in your life, because you’ve gotten older? Where did you get the idea that you should change your style with age? What did you cut from your wardrobe? What did you add? Did you start to dress more formally later in life? More casually? In less fitted shapes? In more muted colors? Were the changes liberating? Confining? Did you come to feel more or less like you? What’s your feeling about the notion of “dressing your age”? Answer as many or as few of these questions as you’d like. (If you’re commenting, please also do me the favor of hitting the heart button ❤️ for algorithmic purposes. Thank you!)
***
As a person who’s prone to all kinds of self-doubt, and self-conscious about not having conformed in certain ways, I seem to discount my existing signature style—a look I describe as: “1970s-Camp-Counselor-Chic” meets “Annie Hall/Esther Hoffman Howard Wannabe” (think menswear and army-navy store influences) meets “In the 90s I lived in the East Village and Wrote About the Downtown Music Scene and Therefore Learned How to Give the False Impression I Was Vaguely Grunge.”
To paraphrase (and bastardize) Donny and Marie, I’m a little bit Meatballs, I’m a little bit rock and roll. Mine is a pretty casual look, although I know how to dress it up when I need to. And it’s pretty classically Gen X. (I find a lot of great clothes that are in keeping with this look at Kim France’s Girls of a Certain Age.)
My closet is filled with lots of old Levi’s 501s—both full-length and cut-off—although also some Universal Thread skinny-jeans; Gap chinos and thrift-store army pants; empire- and babydoll-cut cotton dresses reminiscent of those made by the Street Life brand I bought at NYC flea markets the Y2K era; skirts that hit just above the knee (I’ve finally ditched the super short minis); clogs (although rarely wooden ones anymore, thanks to arthritis); fisherman sandals; Blundstone and old Frye boots; basic cotton short- and long-sleeved tees; tuxedo-style blouses with pin-tucked fronts; classic blazers; menswear vests; and peasant shirts—like this one that I loved so much, I bought three of them (I’ve since given one to a friend):
But as much as I like and feel at home in my look, I’d like to expand my style horizons, at least a bit, especially now that I’m moving into a new age bracket. I mean…I think that’s what I want? It’s entirely possible it’s those societal norms talking again.
Then again, I might also feel a little stuck in a rut. Most days I open my closet and I’m bored.
I’ve also wanted to disabuse myself of long-held assumptions about what I “can” and “can’t” wear based on things like my height and coloring. For instance, I’m trying to let go of the idea that I’m only allowed to wear earth tones because in 1985 a Color Me Beautiful™ affiliate told me I’m an “autumn.” Ditto the idea that I can’t carry long dresses because I’m short, a hair under five feet. I challenged that one last weekend, when I wore this long denim Old Navy number to a pre-wedding party on Long Island last weekend. Not bad, right? (Of course, the dress is calf-length on the model, ankle-length on me.)
So I’ve begun tiptoeing out beyond my usual, trying some new looks.
***
My first stop was an Eileen Fisher discount outlet in Manchester Vermont, where, in late March, I led a personal essay workshop at the Southern Vermont Writers’ Conference. (I’ll be back there next year. Stay tuned for details.) My friend Chris Wells was leading a workshop there, too, and his husband, painter Bobby Lucy, was along for the ride. They were only too happy to give me the Queer Eye treatment.
I had my doubts about this brand for me. There’s a certain simple, clean chicness that appeals. I love the natural fabrics—linen, cotton, wool, silk. (And I like their ethos as a company, especially their commitment to sustainability through Eileen Fisher Renew, through which they sell used, refurbished styles.) In their ads, the models always look stylish, and even a little bit hip. Then again, these days most of their models are young.
In the wild, I’ve mostly seen older women in these clothes, and I hate saying this, but sometimes they appear dowdy to me. The fluid, loose-fitting cuts are so shapeless, and so strongly associated with much older women, I worried they might age me beyond my years.
I went in with the question, “Am I Eileen Fisher Years Old?” I even asked that of one of the sales associates, Tina, 60, and she set me straight—her 37-year-old daughter wears Eileen Fisher, too.
Another question I went in with: “Am I Eileen Fisher Feet Tall?” As I mentioned above, I’m very short, and also curvy. The brand’s flowy, drapey silhouettes seemed like they’d work better on taller, trimmer, smaller-breasted women.
I tried to keep an open mind, though. The staff were kind and helpful. They set up a private dressing room with my name on it, and with Chris and Bobby’s help, they pulled lots of styles for me to try on.
I tried on everything. Most of the styles were too loose-fitting or boxy to flatter my figure. I won’t show you all the fails, but this video captures the general gist:
However, I was surprised to find that many more styles worked for me than I’d anticipated—or could afford, even at outlet prices. I narrowed my favorites down to six or seven items, but only bought three (including two long dresses!), two of them on clearance, and one on sale, for a grand total of $327.
I got this black jersey calf-length dress:
I wore it with a denim jacket to my dad’s 90th birthday party in April:
I also got this silver silk Fortuny-pleated dress, which I wore to a wedding last Sunday. (Forgot to take a photo, sorry.)
And I got this simple knit sleeveless top with a roll neck:
I’m glad we went on this outing, and so grateful to Chris and Bobby for indulging me. It helped me challenge some assumptions about what kinds of clothes flatter me, and to enjoy wearing some styles I previously would have considered too “grown-up” for my taste, and my image.
It was also just fun. When we were done, we went out for Vermont maple creemees—basically maple-flavored soft serve—even though it was snowing outside.
I saw Chris recently, and we talked about continuing on this style journey together, maybe hitting up some of the outlets at Woodbury Commons. Who knows? Maybe we’ll switch it up and I’ll act as Chris and Bobby’s personal shopper, too. Stay tuned…
Your turn…
How old are you? What’s your gender? Do you have a signature style you’ve always adhered to? Or have you deliberately changed your personal style at points in your life, because you’ve gotten older? Where did you get the idea that you should change your style with age? What did you cut from your wardrobe? What did you add? Did you start to dress more formally later in life? More casually? In less fitted shapes? In more muted colors? Were the changes liberating? Confining? Did you come to feel more or less like you? What’s your feeling about the notion of “dressing your age”? Answer as many or as few of these questions as you’d like. (If you’re commenting, please also do me the favor of hitting the heart button ❤️ for algorithmic purposes. Thank you!)
Big thanks to Chris Wells and Bobby Lucy. And to all of you—the most engaged, thoughtful, kind commenters I’ve ever encountered on the internet. And thank you, too, for all your encouragement and support. 🙏 💝 I couldn’t do this without you.
I'm 72 and have always loved fashion, despite my tomboy career. I've dressed for work in jeans most of my career, but also need dressier things for speaking appearances. The only guide I trust is clothing that makes me feel good, and I don't care who the designer is. No heels. No beige/brown/grey. Cute sneakers, sundresses, fun pants, international jackets, lots of pashminas. For my son's wedding I wore a crisp white blouse with a full-length skirt covered in enormous blue polka dots!
Step away from Eileen Fisher As my girlfriend said to me recently, "We may be too old for beautiful, but we can always be cute!"
I'm a 65 year old female. I teach movement so I dress in leggings and tees every day. I have a large collection of leggings and since the pandemic I've moved away from black towards brighter colours to show up better on screen. Making that change was difficult but I'm embracing it.
I can only wear clothes that permit a lot of movement - I can't stand restriction, and that includes shoes. All my shoes are "minimal" with wide toe boxes, which look a bit clownish if you aren't used to them. But once you try them you won't go back to toe-pinching shoes again.
The only change I've made is longer, flow-ier tops (surprisingly hard to find for my 6'1" pear shaped frame).
I am curiously drawn to clothing meant for 20 year olds, like the art tees at Uniqlo, which are not age appropriate but I don't care. When I dress up I usually go for baggy dresses, skirts and pants - Japanese style in black.
In terms of dressing your age - I think of what my mom wore at 40, 50 and 60 etc., but I've never dressed like that. Clothing and attitude towards aging has changed a lot since those days. But comfort and ease of movement will always come first; if I can't squat in it without plumber's crack, I don't buy it.