How not to dress like a middle-aged woman desperately clinging to her lost youth

Good friends can help. Also a nice structured tote.

I don’t know about the rest of you, but Thanksgiving took it out of me this year. I’m tired and grumpy and feeling not even remotely festive. Two days ago, the guy in front of me said “excellentemundo!” to the barista who took his order and I wanted to pinch him. I want to spend the rest of December dressing in black from head to toe, like a Victorian woman in mourning or Masha in The Seagull, and if anyone asks me why I’m wearing all black, I’ll say, “I’m in mourning for my life” in a tragic Russian accent.

But because I’m pretty sure no one wants to read an entire Substack post about my bad mood, I’m instead bringing you an essay about… overalls. Bet you didn’t see THAT coming! (Also, I don’t actually have any leads on a nice structured tote as promised in the title but if you have any favorites, let me know in the comments.)

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My friend Tracy and I are searching for overalls. Not just any overalls; the ones we both owned in the late ’90s when the world was full of possibility and promise. The overalls were faded but not too faded, wide-legged, wide-cuffed, cropped to hit right at the ankle. I’m convinced mine came from Old Navy; Tracy thinks hers came from the Gap. Regardless, we both know exactly what we mean when we say those overalls: slouchy but not sloppy, light but not flimsy, tomboyish but low-key sexy. The ones that looked like the overalls Jennifer Aniston wore on Friends over a white tank. We were no Jen Aniston, but we were reasonably attractive and young—so impossibly young—and why, why did we give them away? We shake our heads. Could we have been any more stupid?

Not me, and also not the overalls, but you get the idea

Tracy and I met when our children were in elementary school. She saw me jogging in the neighborhood, pushing my toddler daughter in a jog stroller, and asked me if I ran. We were standing around near the school playground, waiting for our older kids to finish playing on the play structure, and I nodded and made air quotes around the word “run” because I had taken up running only a year earlier, mostly to get rid of the baby weight I couldn’t seem to shed after three pregnancies in seven years.

Although Tracy was a more experienced runner, she was injury-prone, so our pace was the same: slow. Slow enough to talk while we ran to trade tips on sports bras that didn’t chafe and to debate the least objectionable flavors of Gu, a thick, revolting nutrition supplement that could be sucked down during long runs. Slow enough to discuss the chasm separating before children from after children, when our lives were no longer entirely our own.

We stopped running after Tracy’s injuries got worse and I hurt my calf as a result of wearing Vibram FiveFingers, a minimalist shoe designed to approximate barefoot running. David dubbed them “gorilla shoes” because they were contoured to the foot and had visible individual sections for each toe and zero foot support and he said that I was going to get injured from running in them and I hated that he was right and that the Vibrams did not, as I believed they would, turn me into a fleet-footed gazelle.

By then, my friendship with Tracy was sealed. We started walking instead of running, meeting on Saturday mornings and making sure to include a stop for coffee. We walked past luxurious mansions in north Palo Alto and lamented that we were born beautiful instead of rich and dissected our childhoods and aired petty grudges and nodded at the truth of the saying “little kids, little problems, big kids, big problems.” Because walking, unlike running, did not precipitate heavy sweating, we dressed in everyday clothes and discovered that our styles were complementary, so much so that we occasionally copied each other. During the pandemic, when both of us worked from home, we walked together during every lunch break, keeping the prescribed six feet apart, the same three-mile loop—Louis to Charleston to Middlefield to Mayview to Ross to Colorado. Tracy was the first person outside my immediate family who knew that my daughter almost died after taking a fentanyl-laced pill two weeks into quarantine. The terror and grief of it made me numb, and when I told Tracy what happened she stopped and put her hands over her mouth and her eyes filled with tears and the knot in my chest loosened a little. Every day at noon, we met on Louis Road and walked and anguished about how awful everything was and when we weren’t anguishing, we discussed recipes we saw on Pinterest and houses we coveted on Zillow and Claire’s terrible haircut on Fleabag and Alexis’ outfits on Schitt’s Creek. We spent a lot of time on Poshmark, and that’s how the subject of overalls came up.

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Suddenly, urgently, we need those overalls. We scour Target, the Gap, Old Navy, the entire internet. I find a pair at Target, but the stiff denim bib sticks out awkwardly, and they make me look short and squat and have a slight Whatever Happened to Baby Jane vibe. Mutton dressed as lamb. Women aging ungracefully. We don’t want to be those women.

Then again, it’s possible that I’m no longer the woman I was when I had those overalls. Many years ago, I wore them on a beach trip with David and our oldest son, then a toddler, and we tried to get him interested in the fuchsia plastic bucket and yellow shovel we brought, but he was profoundly indifferent to scooping sand and digging holes and wanted only to run to the water, and we had to take turns getting up and chasing him. He ran in an all-out sprint, not looking back, not checking if we were following, not cowed by the huge waves, and David said that some toddlers had a short rubber band, that invisible elastic that pulls them back to their parents, and that Jordan clearly had a long one. Or maybe no rubber band at all. Jordan was blond and dimpled and chubby and wore a chunky gray knit sweater with a blue house and a red roof on the front, and everyone who saw him said, Awww, cute baby. I turned cartwheels where the sand was firm because my body still moved in ways unconstrained by fear or age. When we returned home and I took the overalls off before bed, sand poured out of the cuffs.

That day, David took a picture of me lying in the sand, propped up on an elbow, my skin golden, my hair tousled, smiling in that unguarded way you smile when you’re young and the world is full of possibility and promise. Less than a year later, Jordan will be diagnosed with autism, and we will have two more children, and I will give the overalls away. My smiles will become tighter, more guarded as the years pass.

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The overalls are our holy grail. The golden fleece. The one ring. The sorcerer’s stone. If we find them, we will be beautiful, powerful, immortal. But they elude us.

I tell Tracy that our quest for overalls reminds me of when I worked at summer camp in Palo Alto in the late ’80s with my friend Nanci. One of our campers was a smart, funny, snarky, skinny, utterly unselfconscious 10-year-old girl who lived in a T-shirt and a pair of shortalls. She was sassy and adorable and we wanted to be sassy and adorable and clearly the way to do that was to get shortalls like Amy had, so we headed to the mall.

We tried on every possible size and configuration of shortalls, only to find that we looked, best-case scenario, comical, and worst-case scenario, stupid. At last, it occurred to us that the shortalls didn’t work because we were in our 20s and had breasts and hips and fleshy knees. The truth of it stung, and we went to La Petite Boulangerie to console ourselves with chocolate chip cookies.

“Yeah,” says Tracy when I finish the story, “but the overalls we’re looking for aren’t shorts. They cover your legs.”

Our quest continues. We go to Savers, a second-hand store in Redwood City, and grab coffee nearby. The barista—tall, slim, her hair in a messy knot at the nape of her neck—is wearing a white undershirt and a pair of wide-legged, perfectly distressed slouchy overalls, because of course she is. They hang on her with careless, casual grace. “Where did you get them?” we ask, leaning across the counter. She shrugs and says, “Oh, a thrift store somewhere.”

Not Savers. Or Plato’s Closet. Or the Goodwill in San Mateo, or Menlo Park, or Palo Alto, or Sunnyvale.

One day, as we’re walking, Tracy says, “You know, I feel like it’s not really the overalls. It’s that we’re chasing our lost youth.”

Of course we’re chasing our lost youth. We’re two suburban middle-aged women who fret over the state of the world and lie awake at night worrying about our children and spend too much time on Poshmark and Zillow, imagining lives we can’t have. It’s not about the overalls at all. The overalls are not the holy grail. The holy grail is having a friend who will text you a link to a Poshmark listing that no longer fits who you’ve become, and you both know this, and you both understand why it’s sad and funny at the same time.

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