It was the first chilly fall night after a hellishly hot summer, and I was crossing one of New York City’s grandest intersections, 59th and 5th, with Central Park spread out before me, a wedding cake of a fountain to my left, and the grand dame, the Plaza Hotel, sparkling behind it.

As I headed west, I noticed a woman heading east: a woman of a certain age, with the style of a bygone era. Her gray hair was swept up and back into a high chignon—surely, a multitude of bobby pins were involved. She had glorious posture, well-powdered skin, and perfect lipstick the color of Burma rubies. She was wrapped in a chocolate brown cape-coat with a circular gold brooch on one side, and I could see her stockings’ sheen in the lamplight’s glow. On her feet were elegant T-strap pumps, and in her hand a shapely gleaming leather purse.

This is how “grown-up” women dressed when I was a kid, growing up on New York’s Upper Eastside. Refined, decorous—ladylike, without a doubt.

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For Love of Stretchy Black Pants

I stopped to consider what I was wearing as I passed her by: Here I was, sliding soon from mid- to late-50s, wearing jeans rolled up at the cuff, trendy black and neon green sneakers, a t-shirt with a silly French phrase on it, and a fuzzy, delightfully soft black hoodie. While toting a backpack.

Somehow, at this moment in my life, the last thing I want to do—or actually do—is stuff myself into clothing that isn’t pajama-comfy. My wardrobe is largely made of stretchy black pants and stretchy jeans and t-shirts and brightly patterned cotton tops—no cuffs, no collars, just clean and simple. Oh yes, and cardigans, lots of cardigans, with flats and socks that have lovely little whorls of fabric inside so they are super-cozy.

The last thing I want to do—or actually do—is stuff myself into clothing that isn’t pajama-comfy.

What’s going on here?

This trend was happening before the pandemic, but of course now the whole drawstring-pants thing has blown up exponentially. It wasn’t alway this way.

In decades past, I turned myself out better. I had, over the years, worn plenty of snug wool blazers, silk blouses (I avoided eating salads in them so as to avoid vinaigrette splotches), pleated skirts, and even a princess-style coat or two. I clomped about in heels and delighted in my Donna Karan Matte Jersey hose. I had fancy, ill-fitting underwire bras that practically left me bruised but they were in such pretty fabrics, I thought, Why not?  

Keeping It Casual

But over the last five or 10 years, things have changed. Part of it must be cultural. We’re at a moment where rules of dress are relaxing . . . like two Benadryls-to-the-wind relaxed. Today, a dress-for-success outfit—a skirt suit and pussy-bow blouse—seems like a costume from the set of Working Girl. Casual Friday, which seemed like a Very Big Deal in the early ‘90s when it took root, has segued into Casual Monday through Friday, led by the hoodie’d culture of entrepreneurs and the business-on-top-party-on-the-bottom nature of Zoom work. 

Looking “like a lady” has also been transformed. Alas, we no longer have Edith Head, Hubert de Givenchy, and other taste-shapers of eras past setting the style standards. Being turned out a la Audrey Hepburn is for special occasions only, if at all. The notion of a well-dressed woman has been turned on its head, discarded even, along with the half-slips and long-line bras our moms used to wear.

Give me one good reason why I should get out of my yoga pants. But don’t bother, because there isn’t one!

“People would think I was wearing a costume if I went to work in one of my ’80s outfits, not that I own them anymore,” says Marsha, who leads the communications department of a hospital in Chicago. “I used to wear a lot of Chanel-style suits with linebacker shoulder pads and colored pantyhose. Stiletto heels. Lots of big, jangly jewelry. It sounds almost funny now, but that was the look then.”

Today, for those who go into an office, a work wardrobe is much less dressed. Eileen, who works in fundraising for an arts organization in Miami, typically wears a lightweight cotton sweater and either a “peasant-y skirt or dark jeans” to work, always with sneakers. “I got that from my young coworkers. They wear Stan Smiths, and now I do too!”

Another reason why our fashion sense has gotten more casual is that many of us work from home—or aren’t in the workforce at all. Says Donna, who recently retired to a suburb of Las Vegas, “Give me one good reason why I should get out of my yoga pants. But don’t bother, because there isn’t one!”

The Fit Factor

The way our bodies change with age also influences how we dress. “I totally see myself sliding into a less ‘done’ style,” says Eleanor of Connecticut, who works as an HR manager. “Part of it is menopausal weight gain. I don’t have the waist I used to, so tailored clothes don’t work for me. I’ve become a ‘skinny stretch pants and big floaty top’ kind of gal. I don’t think I’ve tucked in blouse in a decade.”

‘I don’t think I’ve tucked in blouse in a decade.’

Andrea, of Laguna Beach, a caterer, has the opposite motivation. “My cholesterol went up a lot with menopause, so I switched to a plant-based diet and lost a lot of weight. I do Pilates twice a week, and now I’m a stretch-pants-wearing grandma who likes to show off the results of a healthy lifestyle.”

The Confidence vs. Invisibility Question

But then, when you get right down to it, I have to wonder, do we just stop caring at a certain point because it seems no one really cares about what we’re wearing? There’s been a lot of talk about the Male Gaze, dressing for men, dressing for success, dressing to impress . . . by the time we’re on the other side of 40, perhaps we’re ready to take the foot off the gas.

“I used to dress to turn heads, male heads,” says Theresa, a bank manager in St. Louis. “Short skirts, push-up bras. My self-worth depended on it. I’m not saying it was a good thing, but that was my groove then. Now, I don’t need that. I don’t want men leering at me, and they probably wouldn’t anyway. Comfort over come-hither, that’s my style.”

‘I don’t want to be that older woman with the sensible shoes, cropped hair, and shapeless clothes.’

Is our dressed-down style a sign that we’re sacrificing our sexuality, our power? Or is it the exact opposite?

Penelope, a graphic designer in La Jolla, says, “I consider it a reflection of my confidence that I don’t need to dress in the conventionally feminine, pulled-together way at this life stage. I am happier without high heels and without silk blouses that are hard to care for. I still express my love of fashion, color, and pattern, but I do it my laid-back way. I get inspiration from Instagram, seeing older women in cool jeans and street style.” (Need examples? Look here.)

Interestingly, some women feel just the opposite way. “I am making a concerted effort to dress up more,” comments Wendy of Boston. “I don’t want to be that older woman with the sensible shoes, cropped hair, and shapeless clothes. I want to show that I know how to put myself together and appreciate beautiful things. Even if no one notices. It’s for me.”

Those words almost make me want to “suffer for fashion,” as the saying goes. But I’m on Team Penelope for now, with way-casual clothes that hopefully say I’ve still got it goin’ on. Even if it says that to me and me alone. 

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