Yes, You Can Wear That

What does ‘dressing your age’ even look like?

A few years ago, a middle-aged friend was clothes shopping with her millennial daughter and they gravitated to a women’s store known for its shapeless outfits in muted earth tones— Eileen Fisher.

“Mom,” her daughter said, “you might as well wear a T-shirt that says, ‘I give up.’”

Her daughter was way too young to ever hear about Love, Loss and What I Wore, the 2008 off-Broadway play written by Nora and Delia Ephron, and its famous line — “When you start wearing Eileen Fisher you might as well say, ‘‘I give up’” — but she was hip enough to understand that there’s no reason why women like her mom have to accept a muted earth-toned shapeless fashion future just because they hit a certain age.

If a millennial gets it, then why do middle-aged and older women have to deal with endless stories on what they can or can’t wear, and get peppered with advice to “dress our age”?

“The worst thing you can do is to dress younger than you are,” style expert Kim Johnson Gross advises. (I can think of a lot of things worse for a woman than that!)

Isn’t it ironic that once a woman hits 40 we are told to do everything we possibly can to seem youthful and sold a bunch of products promising “agelessness,” but we are warned not to dress to look younger?

And god forbid if we display our sexuality!

Women just can’t win, can we?

Honestly, I have no idea what dressing my age even means.

I’m no slave to fashion, but six decades into this world I have learned what looks good on me and what doesn’t (and have girlfriends who will be honest with me when I’m clearly misguided) and what feels comfortable and what doesn’t. Am I ever going to wear that a Lycra jumpsuit like I wore in my disco days in my 20s? No, of course not, and it’s admittedly questionable if I ever should have worn it. But you bet I’m still going to wear my jeans mini skirt with cowboy boots despite my somewhat saggy knees for as long as I can; that’s my comfort look (even though Johnson Gross says mini skirts are a big no-no).

All of this came to mind as I prepared for a new author photo for my new book. My old author photo was, well, old. What should I wear for book on busting narratives for older women?

“The scrutiny on women was something I was conscious of when I was picking the photo for my book,” says Jill Filipovic, author of The H-Spot: The Feminist Pursuit of Happiness, in an interview in Racked, which says she was “was cautious to not come across as too girlish, or mean or bitchy.”

Do men ever get told to dress their age or that they can’t wear “that,” whatever “that” means? Of course they don’t. (OK, maybe we can all agree that men can’t wear Speedos unless they’re swimmers, or socks with sandals under any circumstances.) And yet women are bombarded with messages about what to wear or not to wear once we hit our 40s. Society is constantly monitoring us.

Many women are saying screw that by taking part in the “advanced style” movement, which got a huge boost from photographer Ari Seth Cohen in 2008 when he created the @advancedstyle Instagram account as well as a book and documentary about it.

The movement has turned women in their 50s and older into Instagram influencers, using the platform to give a collective middle finger to gendered ageism in the fashion and beauty industries.

It’s about time. Women at midlife and older nowadays don’t look like women that age in years past.

I’m in my 60s. My grandmother looked like the classic babushka, even when she was in her 60s. My mother, who always dressed as if she were a Vogue model, gravitated toward wearing T-shirts and jeans in her 60s. Granted, they were elastic band “mom” jeans, but still a far cry from my grandmother’s matronly clothes. My 60-something galfriends and I dress youthful, stylish and hip. We have not “given up.”

Are we dressing our age? I don’t really know, nor do I care. We’ve learned over the years what looks good on us, with a few mishaps along the way, which is how French women dress, as Pamela Druckerman describes in her book on midlife, There Are No Grown-Ups: A Midlife Coming-of-Age Story:

“In France there’s generally this idea that you should look like the best version of the age that you are. There isn’t this clinging to youth. There is an assumption that women of every age can have their own allure. In France, even the women I know who don’t have ideal proportions know what works on them. Women seem to understand what’s attractive about them and know how to work it and own it and feel good about themselves. That feels culturally different.”

Imagine if that’s what all women heard from a young age — that we have our own allure at every age? I have to think a lot more midlife and older women would feel good about themselves.

Hey, I’m working on a book on changing the narrative about middle-aged and older women, “Acting Our Age.” Interested? Follow me here, on Medium, and on Twitter, Facebook or Instagram. And if you’re interested in changing marriage, please check out the book I co-authored, The New I Do: Reshaping Marriage for Skeptics, Realists and Rebels. You can support your local indie bookstore (please do) or order it on Amazon. We’re also on Audible.

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