I got dumped in a dress. Can I still wear it?

Once upon a time, a few mistakes ago, there was this dress.

It was built by Olivier Theyskens, the Belgian fabric warlock with way better hair than mine. Magically, I found it on the Outnet and could afford to hit the buy button. It was a strapless column sheath in sheen linen, with woven streams of rainbow thread snaking down the fabric. You could also wear it as a maxi skirt, at least if—like me—your shoulders and stomach were around the same width. This rare win for round-bellied girls made the piece feel like even more of a find.

“The Theyskens,” as it came to be known, was one of those fashion scores that made me trust my own body when I wore it. I knew I looked good, and everyone else seemed to agree. “Whoa,” said my editor when I floated by her desk. “Damn,” muttered a doorman under his breath as I wafted through TriBeCa. “Meoooow!” wailed the bodega tabby after I reached for a bottle of kombucha, marking the only time I have been catcalled by an actual cat.

What was exciting, at the time, was that I finally had someone to dress for. He worked for a famous architect and built staircases for designer boutiques. One rainy Sunday, as we played Grand Theft Auto, he paused the game to show me that the boutique we were looting was, in fact, his literal blueprint. Dating civilians as a fashion girl can be a little daunting: We love explosive style, but not if it scares someone off before we can have explosive sex. And though I don’t believe anyone should change their taste for another person’s approval, I do think that dressing for someone else’s comfort and joy can be a fun act of generosity. (This is not my idea, sadly. Rachel Comey turned me onto it.)

Before, my date-night clothes had hewn closely to Penny Lane’s tour looks: black leather miniskirts from Chloé, denim button-ups from Uniqlo, Rebecca Minkoff boots I’d scrape against a dive bar floorboard if I got nervous (often) or bored (also often). Finally, coupled with someone who knew KidSuper was a fashion label and not a Pixar cartoon, I pulled out the Theyskens for our first date.

“That’s cool,” he nodded when I floated up to our dinner reservation. We spent the rest of the night comparing the most outrageous asks from our demanding bosses, trading stories about camping disasters, and debating how much our parents actually needed to know about our lives. It was the first time I didn’t have to explain the split between my job and myself to a guy. I felt understood without feeling exposed. This was new to me, and it made me feel braver when saying basic words like boyfriend and commitment.

It made me braver with my clothes, too. Out came the Stella McCartney bubble-hem skirt with a Vlone hoodie and plastic Melissa heels. Hello, tiny tweed shorts from Louis Vuitton, vintage cowboy boots, and a Blair Waldorf blazer. I think there were some Alice + Olivia painted bell-bottoms with Heron Preston rugby shirts and old black Prada heels in there, too.

It’s the first time I remember dressing as my most creative self, instead of the usual “sexy, but, you know, chill about it” avatar that so many of us have chiseled into existence somewhere between our third and zillionth “nice to meet you” cocktail. I thought because I felt brave aesthetically, it must mean that I felt secure emotionally. “If I can show my true style with this guy,” I reasoned, “that means I can be my true self. And he loves me anyway. That’s a really good sign … right?”

Well, yes. Sure. But also: Hopefully, the older you get, the more often your inner voice and your outer self hold hands. You don’t need a relationship to prove that. (You don’t even need a pair of Miu Miu clogs, although it’s okay to pretend you do while gently letting go of your credit rating.) What’s actually important in adulthood is to practice saying stuff to other people.

Things like: “Thanks, potential client. Do you have any flexibility on budget, because my fee is normally higher?” and “Family member, I love you, but my body is not a topic of conversation,” and “Friend, maybe your wedding reception doesn’t need to include a mandatory sweat-lodge cleanse.” Or, in my case, it would have been saying to this particular man, “Boyfriend, I love you, but we haven’t really talked about our separate goals as humans. Maybe we should do that before things get too far.”

Things, of course, got too far.

The day he dumped me, I was feeling unstoppable. In part, that’s because I was wearing the Theyskens—this time as a skirt, with a David Bowie tee on top. When I skipped down my apartment steps to meet him, I felt like a tiny wind machine was puffing at my hem, turning the fabric into something like sea-foam. Could I be a vintage T-shirt Venus? Hell yes, I thought, and of course, I was wrong. We were on an East Village coffee bench when I asked where we should go for Labor Day. I remember his smile went flat, like a paper airplane snatched and smooshed by a stern teacher. “I don’t know,” he said. “I’ll probably just stay home. Actually, I’ve been meaning to mention …” He’d been feeling lost in his own routine. Maybe he’d move somewhere else. Maybe he’d be someone else. Maybe he just needed time, or therapy, or cocaine. He didn’t know what he wanted, but he definitely did not want me.

That’s how I heard it, anyway, and I noticed for the first time how my tears slid down my neck in the same streaky lines as the Theyskens’ rainbow seams. Meanwhile, my mind raced from confusion to shame. Hadn’t things been fine? What clues had I missed? How did I not realize? Why was I so dumb? How could I think he wanted me? Nobody ever wanted me. I was broken. Also, ugly. Also, ugh, this fucking dress. I wanted to crawl out of my life, and definitely my outfit. I felt like someone had pulled a trapdoor from underneath the sidewalk, without telling me I was about to fall. It was the first time the word dumped made corporeal sense to me: I had been emotionally thrown overboard.

I ran home, unzipped myself, and climbed into bed in my underwear. The Theyskens stayed crumpled on my floor for weeks. At the time, I couldn’t tell you why I refused to touch it—maybe I would have said something like, “It’s carrying bad energy.” Looking back, I think the feelings behind the fabric go something like this: The Breakup Dress, as it was rechristened in my head, seemed to symbolise an ultimate delusion. I had kidded myself into thinking I was beautiful, cool, wanted. The con was my confidence, and I had taken it way too far.

Months after the breakup, I continued second-guessing everything around me. If that relationship hadn’t been as real as I thought, was anything? Obviously, I was also kidding myself about that perfect dress. Probably also about my competence at work. About the strength of my friendships. About my worth. I let myself unravel to the point where anything good I’d achieved felt like it might be a lie. The empress had no clothes … and no right to think she was a lovable human, either. I truly believed I’d gaslighted myself into believing I was wanted, or capable of a real relationship, or capable of looking good in a designer dress. For a variety of reasons—the primary one being, I’m human—it was a tough belief to shake.

But I am not a Buccaneers heroine, and without an invisible pillow of wealth propping me up, I had to get out of bed eventually. It even meant cleaning my room, though the Breakup Dress stayed balled up and kicked into a corner. Trashing it felt silly and immature. Reselling it seemed insane—I love the RealReal, but let’s be real: I’d barely get enough from it to buy myself a martini. Did I want to tell one of my friends to wear it? No … but I couldn’t bring myself to, either. Instead, I zipped it into a garment bag where I didn’t have to see it, and shoved it behind some winter coats.

It stayed there for another few months, until a little voice in my brain said, Hey, don’t you miss your favorite thing? I wish I could say it was because I found a great therapist, or started a gratitude journal, or came to terms with the fact that boys are dumb and I am fine. But I think it was the opposite: I still felt shaky in myself. I needed proof that I could walk in a straight line anyway.

Tentatively, I began wearing the Theyskens again. First, it was just to the deli, where the bodega cat gave me some approving purrs as I scoured for Oreos. Next, I threw it over a tie-dyed Grateful Dead tee for brunch. I felt a little hyped up as the rainbow threads of the hem hit my knees, and my friend Shiloh told me it was the first time I’d seemed like myself in weeks. “Really? In the Breakup Dress?” I asked. “What’s that? I thought it was your Theyskens!” she said. It felt like a reset button going off in my guts. Or maybe that was the beet puree on my breakfast plate. Who knows.

Ready for the fast-forward? It’s been about six years since that breakup. I have a new partner, a new apartment, a new job, and (yes) a new therapist. But I still have the Theyskens. I wear it often, though every time, it feels like a dare—will somebody tell me, again, that I’ve vastly misjudged my own belonging in their life? Have I overshot how big my piece of the world should be? Will today be the day that every door slams shut? And then, no. It’s just another day. Sometimes it’s good. Sometimes it’s bad. The dress stays the same.

A few months ago, I was commuting from work on a packed subway car and wearing the Theyskens as a skirt with a beat-up Burberry peacoat, a fisherman sweater, and cowboy boots. As we pulled into the next station, the train jammed with more people, and my ex’s unmistakable face came into view across the aisle. We both did a minor double-take. He had gray hair and a beard; my hair—corkscrew-curly and red while we dated—was ice blonde and straight. Then he glanced down and saw the fabric of my skirt, and his jaw tightened. It was me. Same skirt. Same girl. I looked away and walked out at the next stop.

As the subway pulled away, the hem of the Theyskens fluttered from the whoosh of hot air. I took a few steps forward and the skirt swished around me. Then I took a couple more. And a couple more.

This article first appeared in harpersbazaar.com in August 2024. 

Lead Image: FARAN KRENTCIL

Also read: We need to stop seeing a break-up as a failure