How I Dressed to Heal My Heartbreak

In fall 2013, I was crying to a friend on a Brooklyn-bound train when a perky stranger reached out and waved in my direction a tiny red copy of “Awakening Loving-Kindness.” “I think you need this more than I do,” he said. I took the book, thanked him and examined the photo of its author, Buddhist nun Pema Chödrön, on the cover. Someday, I’ll read this, I thought.

Then in June 2017, “someday” came. It was two days after I turned 29; 10 days after a devastating breakup (I was wearing a vintage Comme des Garçons dress that still hurts to look at); and three years and six months after I made the difficult decision to cut ties with my mother. The inescapable weight of my grief told me this was the time — now, not later — to finally pick up the book.

I spent the end of that summer studying an ancient technique called metta — or lovingkindness, as it’s translated in English. This type of meditation involves the repetition of mental mantras: May I be safe. May I be happy. May I be healthy. May I live with ease.

It is said that the Buddha taught metta as an antidote to fear, which appealed to me as a newly single woman struggling to unpack a lifetime of toxic internalized messages and knee-jerk self-destructive behaviors. Knowing it was going to take more than a brief, daily practice to heal my heart, I went home and entered an online lottery for a weeklong retreat the following spring, which was to be held at a New England meditation center. Participants were to observe noble silence — meaning no reading, writing, speaking, or eye contact. By the end of fall, 100 names had been drawn. Mine was one of them.

Up until recently, one of my only productive strategies for working with fear was dressing with intention — draping myself in loosefitting clothing that tempered my body’s sexuality; procuring status-symbol items to signal I belonged; and peppering my wardrobe with kooky statement pieces to attract kindred spirits. I learned at an early age that clothing could shape how people see you, but now it was time to take a closer look at how I saw myself. I never imagined life would lead me to a silent retreat, and I wasn’t prepared for what it might have in store. So I did what I always do when life feels out of my control: I planned a week of outfits.

When I arrived in rural Massachusetts after traveling by train, bus and car from my apartment in Bedford-Stuyvesant, Brooklyn, I was wearing black linen pants that I had thrifted in Arizona, where I’m from; a boxy long-sleeve tee I bought on sale at COS; and a heavily discounted pair of magenta-and-gold Asics sneakers I’d purchased online two years earlier with my ex-partner, who owned a lime green pair. The shoes were part of a loving nudge to get me to take up running, which he thought could help my anxiety. What he didn’t realize was that I had anxiety about running, too. My mom was a runner. It felt like a slippery slope. More than a year had passed since our weekend jogs around Greenpoint, but even after all this time, the Asics still made me feel safe. I finished my outfit with a comfy pair of alpaca-blend socks that felt appropriate for this phase of my life. They said, simply, “OK.” I stepped through the door of the retreat center. There was no turning back now.

As I was settling into my dorm room that afternoon, hanging my clothes and making the bed, it occurred to me that I should save my favorite shirt, which I’d acquired on a beautiful trip to Mexico despite being told not to go there, for safety’s sake, as a pick-me-up should I need it, or a celebration should I succeed. The shirt was hand-embroidered with happy-hued flowers, and was the crème de la crème of a wide textile collection I’d amassed over the years — each piece a reminder of home.

But like anything else, “home” was complicated. It was desert walks, Instagrammable sunsets and time with loved ones; it was also feelings of unworthiness, troubling memories and immense sadness. It was lucky thrift store finds, adobe blocks in Barrio Viejo and the joy of Arizona sunshine on my skin; it was also shame for not speaking Spanish, guilt for leaving and “don’t get too dark,” a warning I’d hear every summer as a kid. This is what I was working with. This is why I was on retreat.

On the first full day of sitting, I wore a pajamalike J. Jill linen pant set, scooped up in an eBay auction. It was loungewear at its best: loose, breathable, and the color of Sedona’s majestic red rocks. Something about the hue felt warm and right.

By lunchtime, it was clear to me that a watch, shawl and slippers are the accessories that best serve someone who attends a silent retreat. Luckily, I had packed all three, taking the advice of the retreat center’s website, which urged participants to 1) be prepared and 2) be comfortable. In addition to ample outfit options for the unpredictable spring weather, I’d also brought an assortment of functional and decorative extras, which I wore intermittently throughout the week: Adam Selman x Le Specs mirrored sunnies that I bought myself for Christmas; a Patagonia fanny pack worn unironically around my waist; two cotton bandannas; a brand-new tube of bright red Mac lipstick; a headlamp purchased at Paragon Sports; tiny hand-me-down hoop earrings from a former colleague I admire; a baseball cap I bought after a hike with my little sister; an oversized black cashmere sweater I got for $2 in a Southern Arizona retirement community, and a loose quartz crystal charged at Joshua Tree’s Integratron, for good measure.

Sartorially speaking, Days 2 through 4 are all out of order in my memory, but I can tell you this: There was a red bandanna worn as a neckerchief, along with a white linen shirt from Uniqlo, brown linen pants from eBay and my sage Barbour coat, which I bought new with tags from a fashion blogger on DePop. I remember that outfit was still early in the retreat, and how, looking in the mirror after a particularly difficult sit, I found stability in the fact that I was wearing a hankie. Unlike my Barbour coat, which retailed for a price so high that wearing it felt like living in a fancy new condo with waterfront views, my bandanna had nothing to prove. It was a cheap and cheerful pop of flair that served no purpose other than self-expression. And what it expressed was happy.

Then there was the day I threw on my favorite indigo vest, which featured interesting arm hole shapes and bright bands of embroidery. What I especially loved about this vest was that I had found it on Etsy — and it fit. The whole thing seemed to me a stroke of great luck, like when I was hired to work at their Brooklyn headquarters fresh off my move from Arizona. Walking into the shrine room at retreat that morning, I noticed that one of the teachers — the British one, whose accent sounded like my ex’s — was wearing a vest, too. Though these first few days were grueling, it was kind of wonderful to be here, so many of us connected by metta. And vests.

Another day, a cloudy day, I decided to go for a run. I was filled with so much anger and grief — at myself, at my situation, at the world. As I slipped on my Nike sports bra, I thought about the story behind it: how my ex-partner had taken me to the company’s store on 57th Street and offered to treat me to some new gear. We had just returned from celebrating Christmas with his family in England. It was too much. I didn’t deserve it, or so I told myself. I insisted that we leave and look for cheaper athletic wear at T.J. Maxx or Marshalls — the places I’d shopped with my mother growing up. Looking back, that was the beginning of the end.

Then I remembered the practice. May I be safe. May I be happy. May I be healthy. May I live with ease. I repeated the phrases silently while I finished putting on my clothes, and during my entire sprint up the road and back. Every time I passed a house, a car, even a critter, I extended the wish toward it, too.

For my afternoon walk on the fifth day, I dressed in white so I could easily spot ticks. My ensemble included a pair of white linen capri pants I bid on before I understood how eBay works and a white linen Uniqlo button-down. I topped off the look with my faded green butterfly cap, which I had come to regard as an emblem of transformation — a badge of honor for spending the last few days tapping into a genuine wish to be happy. I had never wished this for myself before. I never thought it was possible. As I headed out, I tucked a trail map into my black Patagonia fanny pack, along with a Kodak Fun Saver to remember the woods by. I brought the camera in case there was something I needed to document, and this walk felt like the right occasion. By this time tomorrow, we’d be gearing up to speak again; in two days’ time, I’d be on a Peter Pan bus headed to back Port Authority. But for now, I practiced metta for all beings, even the ticks, and stopped for a second to snap a photo of the road unfolding in front of me.

On the evening of the sixth day, we started using our voices again; I had just the outfit. I slipped on my Mexican embroidered shirt. I had made it through somehow, and this shirt was my celebration. Though I’ve worn it dozens of times before, this one was different.