“And you may ask yourself, how did I get here?”

Those were the Talking Heads lyrics pulsing through my head as I froze in fear, sweaty in a dressing room at the Fifth Avenue Aritzia in Manhattan.

The sales clerk’s gentle tapping on the door was followed by a sweet, “How are we doing in there? Can I take a peek?”

Inside that dressing room, I felt 40 kinds of foolish. As if I’d been invited to a Grease!-themed party and was test-driving a costume.

No. She most certainly could not take a peek.

Because here I was, a woman in her 50s, who had just wedged herself into a pair of faux-leather leggings and who was too ashamed to have anyone gaze upon this folly.

“I’m fine, thanks,” I said, but it was a lie. I was not fine. I was realizing I no longer had a clue how to dress myself.

Adventures in Legging Land

Goldie Hawn (here at age 57) is all for dressing outside the lines.

The faux-leather legging craving had descended upon me about two days earlier when I saw a photo of a somewhat younger friend of mine on Instagram wearing a similar pair of leggings, with a big blouse and cute kitten heels. I wanted to look like that—a woman at midlife who still had style, but didn’t look ridiculous. You know what I mean by ridiculous—”mutton dressed as lamb,” as the saying used to go.

I had wanted to show that I was still cool, still up to speed on the trends. But inside that dressing room, all I felt was 40 kinds of foolish. As if I’d been invited to a Grease!-themed party and was test-driving a costume.

So I peeled myself out of the leggings and got ready to return to work in my usual baggy, basic black clothes. But then I looked on Instagram again. There was the photo of my friend, laughing and looking lovely in what I now knew were officially called “vegan leather” leggings.

I walked up to the register and bought the damn things, feeling all shades of Chrissie Hynde.

But the next morning, when I saw them sitting on the chair by my bed, I felt none of that badass power. Instead, I was slapped by sickly waves of regret, like waking up after a wild party and wondering, “Did I really drink that much/put on that platinum wig/offer to lead a line dance?”

Morning-After Regret

Who was I kidding? There I was most mornings, slathering on crepe-correcting skin cream and

Halle Berry, 51, looking every inch age appropriate.

scanning for any new gray-hair invasions. It was as if I was living a perimenopausal version of “One of these things is not like the others.”  We don’t belong here, the leggings seemed to smirk.

I was embarrassed—mortified, even—that I thought I could ever see the light of day in this garment, and returned the leggings ASAP on my lunch hour. For some reason, I felt compelled to lie to the sales clerk that I had bought them for my niece but—D’oh! she already had a pair.

On my commute home, I thought about how easy it used to be to get dressed. Through all my years in New York City, working at fashion magazines like Vogue and Mademoiselle (remember that one?), I loved clothes. Skinny jeans, paper-bag jeans. Leggings, mini-skirts, maxi skirts. Power suits, sun dresses, bias-cut dresses, bias-cut dresses worn with Doc Martens. I was there, part of the pack that could make it work. It was a fun game of dress-up every single day.

Knowing My Age

But now, in my 50s, it’s harder. Styles have loosened up, for sure, but part of me still finds myself asking, especially when I’m lured into an Anthropologie by a cunning window display, “Can I wear that? Am I too old? Do I look like I don’t know my age?”

We don’t belong here, the leggings seemed to smirk.

As my train lurched to my stop, it occurred to me: I do know my age. And it’s my job to represent it however I please.

So the next day I marched myself right back to Aritzia on my lunch hour, grabbed the forbidden leggings, and headed to the register. The same associate was there as yesterday. She recognized me, and said, “Oh, you’re back!”

“Yes, I decided I needed a pair of these for myself,” I told her with a big smile.

“You do,” she said. “Every woman on the planet does, amirite?”

Shiny Spidery Legs in Manhattan

Janet rocking the vegan leather leggings in Manhattan. Photo by: Jason Harper

The next Saturday, I pulled out the snaky garment and told my husband to brace himself, my new vegan leather leggings were spending the day with us.

I put them on with granny boots and a big old Esprit sweater from about 1986 that usually lives in my attic.

Off we went, him telling me I looked hot. Every time I caught my reflection in a storefront window, I had a stupid grin on my face, happy to see my shiny spidery legs moving through Manhattan. It took me back to my 20-something days (hell, I even heard Depeche Mode’s “Black Celebration” in my head) and made me feel still stylish and modern, regardless of the fact that I was born in the 60s and conventional wisdom would have me clothed in Chico’s and Talbots.

When I took the leggings off that night, I thought about a beloved, and hugely flattering, card a friend had sent me on my 50th birthday. She had written that she wanted to give me a shout-out for being a woman moving into midlife with plenty of style and making some surprising, inspiring life choices.

I couldn’t help but think: And now I have a wardrobe to match.