I Had a Mid-Life Fashion Crisis

When my daughter was 4, she had very clear ideas about what to wear—and they did not include anything that matched. Orange tights with a purple-and-green dress. Plaid with polka-dots. Stripes with, well, more stripes.

Not wanting to look as if I were aiding and abetting in what I deemed her fashion crimes, I pinned an “I dressed myself today!” button on her outfits in the hopes that I was building her self-esteem while preserving my own.

But as I leafed through Vogue at the dentist’s office, it hit me. My daughter’s outfits looked a lot like those on the models.

Mine, on the other hand, were just as my little fashionista claimed: “too matchy.” Maybe I was the one who shouldn’t be allowed to dress herself.

Looking back, I come by this love of color-coordination honestly. My mother, hospitalized for a hysterectomy, once sent me home to fetch a watchband to match her robe. As a child, I wore ribbons that matched my socks which matched my gloves, which matched everything else—all courtesy of my mother’s fashion mandate.

A recent University of North Carolina study made it official: Their conclusion was that “matchy-matchy” (their words!) was as big a fashion faux pas as combining patterns or colors that clash. Kurt Gray, lead researcher of the study published in the scientific journal PLOS One, found his inspiration over a few drinks with friends. “We study things that matter to people,” he says. “How about fashion?” Far from being superficial, fashion “matters in whether you get a date or whether you get the job.”

I need neither date nor a job. But as mother to three kids, including two teens, I could use some fresh street cred. As a menopausal woman whose formerly fit body has been hijacked by hormones, I could also use some self-esteem. As a woman whose jackets match her pants, whose eyeshadow matches her blouse, whose socks (hidden inside boots selected to match her handbag) match her pants, I could perhaps use a full-blown intervention.

Two weeks later, I met a friend at a store she loves and, she assured me, is owned by a woman who would guide me toward this fashion sweet spot, whereby my clothes would match … but not too much. Eyes cast to the ground, I made my confession. “I need a new dress,” I told the shop owner. “And”—I swallowed hard—“I tend to be too matchy-matchy.”

The owner sighed. She’s met women like me before: Middle-aged. Tired, literally and fashionably. I imagine that she sees my mother.

An hour later, I left with a black dress, with which I planned to wear black pumps. I mentally patted myself on the back when I noticed that they had a taupe-and-black snakeskin heel. This was going to be harder than I thought.

I went online and downloaded Stylebook for $3.99 and committed to photographing all my clothes with my phone, uploading the photos and then letting the app unleash its fashion magic. I was told that my photos are crap—either my background was the wrong color or my lighting was poor. Though both Stylebook and iCloset (another popular app) regularly receive accolades on social media and in the press from more tech-savvy dressers than me, I was growing impatient. It seemed like way too much work to invite an algorithm into my closet to tell me what to wear. I decided to enlist my teen to do the photographing (I did, after all, spend almost four bucks on this) and tracked down a flesh-and-blood fashion mentor.

I found Layla Katz, lead stylist with Stitch Fix, a San Francisco–based company that provides clothing and fashion advice to its clients by compiling a core wardrobe, boxing and shipping it. Though Katz understood my dilemma, matchy-matchy had never been a problem for her. “I have always steered away from it,” she said. “To me it didn’t feel chic or fashionable to have my handbag match my shoes match the trim of my dress.” I was thankful this was a phone interview so she couldn’t see my face blush with shame. But, she said, “I don’t think we live in a fashion world where the rules are hard and fast.” Take Japan, she said, where matchy-matchy is “very chic and cutting edge.”

I wonder, briefly, if she’s suggesting I move there.

Next I enlisted Jennifer Slay and Rita Perepelitsky (it takes a village!), a stylist team that has seen plenty like me. They’re two of the four founders of DailyGlam, an online styling program that provides fashion advice and wardrobe suggestions to those who pay the $25 subscription. They also provide in-home consultations but I arranged to meet them in a coffee shop. Agonizing over what to wear, I finally selected black leggings, black boots, and a gray cashmere turtleneck. My purse was, you guessed it, black.

The pair taught me about “creating illusions” by placing color strategically (black recedes, light colors draw the eye). They told me that confidence was the “main ingredient to a good outfit”. They talked about pears and apples and hourglasses and diamonds—insisting that the first step was for women to know their body shape so they can dress it properly. They told me that you could even mix leopard print and polka dots—“It just depends how you wear it”—which confused me. And then Perepelitsky told me something that blew my match-loving mind.

“Use a color wheel,” she said.

“When you think it doesn’t match,” said Slay, “it actually does because it’s based on the wheel. What you want is to complement—it’s the opposite color that complements that shade. So in fact it does match.”

Layla Katz agreed. “If you can figure out tones and shades that work together within a family that aren’t completely matched, it lends an air of cohesiveness to your look.” To help with this, Stitch Fix posted a color wheel on its site.

I wondered how I made it through life without knowing about this magical wheel. What’s more, Jen advised me to just go into my closet and put things together without worrying about whether they match. “Just see,” she said.

It felt revolutionary but something in me shifted.

The next day I looked in my closet. I ignored the black leggings in favor of a pair of cream cords I bought on a whim. I added a camel-black-cream-striped turtleneck that has long been overlooked. And then—wait for it—I added a pair of leopard flats. When I left the house, I put on a black leather jacket but still. Leopard and stripes.

I felt ridiculously excited. I felt … young.

I sent Jen and Rita a selfie, though it took me a solid ten minutes to realize I needed to find a full-length mirror in order to photograph the whole outfit. I received a “very nice”—all caps and three exclamation points, followed by the suggestion that I wear a brown leather jacket and red purse. Red purse? That wouldn’t match, I thought. Perfect.