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Am I Too Old for Overalls?

On aging, the '90s, and what happens when Madewell starts selling your memories.

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In the ‘90s, overalls were ubiquitous. They fit like flour sacks, straight and lifeless. Winona Ryder wore hers baggy on the cover of Rolling Stone, her bare skin shining underneath. T-Boz, Chili and Left-Eye wore theirs as a political statement with condoms clipped to the fabric. My first pair of overalls were Levi's. I bought them at the flea market at the corner of 77th and Columbus Avenue along with a pair of used Levi jeans.

"You don't wear them enough," a boyfriend once told me. "You're so cute in them." So I wore them daily, during a three-week road trip from New York to California. There I was, in my overalls, surrounded by the blanched gypsum crystals of White Sands, New Mexico. With the red rocks of Sedona behind me. The Pacific Ocean by my side. My overalls were magic sheaths of indigo and I was a free spirit, an Americana bohemian. But really, I was emotional and anxiety-ridden about my future, only feigning apathy.

By the mid-to-late ‘90s, overalls became a relic. Low-rise jeans phased into skinny jeans. I phased into a mom of two kids with wider hips.

By the mid-to-late ‘90s, overalls peaked. Britney Spears and Kate Moss swooped in with low-rise jeans like Drogon on a fire-breathing rescue mission, and quickly, overalls became a relic. A fashion dinosaur. Low-rise jeans phased into skinny jeans. I phased into a mom of two kids with wider hips.

And then about a year ago, along with Birkenstocks, flannel shirts and jumpsuits, overalls made their way through fashion's revolving door. Soon, Gwen Stefani, Heidi Klum and Sarah Jessica Parker were wearing the uniform of my youth. So I obsessed a little, studying Gwen Stefani in her overalls. After all, we have so much in common: She's a mom in her early 40s; I'm a mom in my early 40s. She has washboard abs; I also have a torso.

Actually, our torsos—mine and Gwen's—are each other's yin and yang. Our bellies are opposing forces, two halves of the same big circular whole that is the challenge of getting older. The soft, squishy side represents the regular people, those of us who don't have the time, the wealth, or the interest to obsess over our weathered bodies and faces. The rock-hard abs side is the side that barks the tenants of beauty, the side that's somehow figured out how to obey the unrealistic standard set by fashion magazines.

There are rules to aging just as there are rules to fashion. The number one rule: do not look as if you're getting old. Rule two: dress your age. Rule three: don't be sexy. "Stop wearing tight, revealing clothes," says Harper's Bazaar, because ageless fashion is about being "adored" but "not ravaged." If you're 40, wear this black sheath, writes another fashion mag, because when you're 40, you should dress like every formal occasion is a shiva call. One Daily Mail survey said women shouldn't wear bikinis past 47. Or wear sneakers past 44. Somebody get me my muu muu.

Amy Schumer calls this phase of a celebrity's life "your last fuckable day"; it's the day that the media decides that actresses are no longer sexy, desirable, or, yes, fuckable. It's the day an actress competes to be Jack Nicholson's love interest. Or the day she goes to wardrobe "and the only thing they have for you to wear are long sweaters."

There are rules to aging just as there are rules to fashion.

I call this the dawning of Eileen Fisher. And while I've grown to love Eileen Fisher—this is what happens in your 40s, you stop wishing you could wear crop tops and dream about long boxy shirts—her clothes are, as The New Yorker's Janet Malcom observed, "for women of a certain age and class."

Of course, I could have picked anyone instead of Gwen Stefani to be my fashion inspiration. I could have chosen Kim Gordon, who looks fuckable in every single Instagram picture in her feed. Her sex, booze and tattoos necklace is one massive, unapologetic middle finger to the bible of fashion decrees. But it was Gwen Stefani who wore the overalls. She's refreshingly weird and playful. She doesn't seem to want to turn back the clock. She recycles fashions from her youth and she perfects them the second time around.

Madewell had at least four pairs of overalls, and the model in the catalog wore them with a black blazer and slide-on leather sandals. These weren't festival overalls, I told myself. They were a sharp look now. Like a bucket bag. Or culottes.

Or maybe I just was drawn to the overalls because they inspired nostalgia about my youth, like early Madonna songs or video stores.

"Am I too old to wear these?" I asked my husband, pointing at the catalog.

But a good husband, or a good friend, will never deny a fashion whim. They'll say, "You've been thinking about this for weeks. Just get them. You can always return them."

Madewell described the pair I ordered as having a "slouchy fit through the hip with a relaxed, slim leg," but I couldn't drag them over my hips without having to suck my gut to my ribs. The waist of a pair of overalls is not supposed to be tight, in my experience, and theoretically the apron should gap slightly, but these strapped in my breasts.

When I complained about the fit to a friend, she explained it this way: "I'd love to get a pair of overalls, but the new overalls are smaller in the hips and my boobs are bigger. You can't wear overalls with big boobs comfortably."

In your 40s, you learn there are no biggest mistakes of your life. There is just a series of mistakes.

I remembered a Tim Gunn lecture where he scolds some poor woman about dressing like an awkward adolescent. "Dress for who you are now," he tells the woman. Which was my intention when I bought the Madewell overalls. Yet, no matter how I framed it, overalls still felt like a statement from my youth, which I had a hard time embracing because they felt exactly like that—too youthful. Like I was trying to be an age that I'm not, or worse, that I was wistful for that age. That I wasn't satisfied at the stage of my life that I was in. (Which I was. I am.)

I enjoy my 40s more than my 20s. This is a surprise, I know. In your 40s you have to use lightening cream, you take more Advil, and you use words like "poser" even though no one knows what you're talking about. But my 20s were filled with insecurity and shitty relationships and bad sex I mistook for good sex. I was always on the verge of a big change or a major regret. I often said to people, "I think I'm making the biggest mistake of my life [fill in the blank: moving from this city/getting engaged to this person/leaving this job]."

In your 40s, you learn there are no biggest mistakes of your life. There is just a series of mistakes.

This goes for fashion too. When I was 18 I wore a double-breasted suit with a bra peeking through as a direct result of Madonna's "Express Yourself" video. There were Z. Cavaricci's. Fanny packs. Then in the ‘90s, between the overalls and jeans, I went through a goth-meets-grunge phase, wearing a daily cocktail of black leggings, a flannel shirt and black suede booties.

Maybe every generation feels that their look is more authentic than the one that follows.

Recently, my sister-in-law, Melissa, a fashion designer, and I stopped in Urban Outfitters' massive 34th Street location in Manhattan. It's an alternative time warp, a ‘90s mecca, with rows of vinyl and boxy t-shirts straight out of a Luscious Jackson Gap ad circa 1997.

We talked about the overalls and I asked her if she was going to wear them. "I'm not going to wear the skinny ones. I'm going to wear my version of them, which is roomier and comfier. I just have to find the right pair," she said. "I think as you get older, you start to know what you like and what you don't like."

We meandered into the shoe section, which was taken over by Birkenstocks. "Do you understand how I wore my Birkenstocks to death in the ‘90s?" she said. And then she bought herself a black pair.

While Melissa modeled her new Birks, I faced the mirror to get a glimpse of my outfit. My ripped jeans. My boxy, gray t-shirt with the rough-edged collar. My look hasn't really changed much either. Except I pay for the holes in my jeans now. And when I put on a "boyfriend sweater," it's not a sweater belonging to someone else's actual boyfriend.

Fashion was more nuanced in the ‘90s, less calculated and more guttural. Or maybe I was just more guttural when I was younger. Maybe every generation feels that their look is more authentic than the one that follows.

So I sent the overalls back the next day. I don't know if I'll ever find a pair that fits. And maybe I don't care so much. Not because I'm afraid of embracing a style that defined my youth, but because maybe overalls aren't right for who I am now. That's the beauty of being a mom in her early 40s—I don't have to search anymore. I already know what looks good on me.

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