What to Wear to Your Break-Up

What I wore to my last major break-up, in 2014
What I wore to my last major break-up

Break-ups are hard. That’s true for anyone, and it’s true for me. I have an anxiety disorder. That means my brain’s fear-o-meter is out of whack. And that means I often worry about things that no neurotypical person would ever worry about as deeply as anxious folks do. For example: what to wear to break up with someone.

There is such a delicate balance to be struck in this sartorial decision. You want to wear something that makes you feel strong and brave, shoring up your resolve so you don’t chicken out. You want to look good, but not so attractive that your babeliness is a slap in the face to the person you’re dumping. You want to be prepared incase your soon-to-be-ex bursts into tears (or you do) and needs to wipe their snotty face on something. You want to dress appropriately for the temperature and tone of your break-up’s setting, whether that’s your beau’s apartment, a classy bistro patio, or a bustling street corner. You want your choice of footwear to enable a quick getaway, whether that’s needed because of emotional awkwardness or (god forbid) actual threats or violence from your scorned would-be ex. And you don’t want to wear anything that could be interpreted as a sign of lingering feelings for your dumpee, like a T-shirt you inherited from them or a necklace they bought you.

The last time I broke up with a serious partner, it was the sticky height of summer in 2014. I tucked a white tank top into a pink skirt, and put my hair in a ponytail with a pink scrunchie. Hot pink is one of my “power colors,” a shade that makes me feel strong and put-together, which I knew I’d need – because emotionally, I was a mess.

I slipped on some plain black leather flats and departed toward where I’d agreed to meet my boyfriend. About ten minutes into my walk to the subway station, I realized that in my frazzled trance, I’d forgotten my wallet at home. It was too late for me to run back and get it if I was going to meet my partner on time, so instead I just power-walked all the way to my destination. I arrived dripping sweat and out of breath.

When I actually delivered my little break-up speech, I broke down crying. I’d been with this man for three and a half years, and he was my best friend; saying goodbye to him was no easy task, though I knew it was necessary. He asked me if it would be weird if he hugged me, and I said no. He squeezed me tight, one last time, until my breathing slowed. And then we said our teary-but-amicable goodbyes and went our separate ways.

I wished I’d brought a scarf, so I could’ve wiped my wet face on that instead of on my beau’s shirt. I wished I’d brought sunglasses, so I could’ve hid my eyes as I wept all the way home. I wished I’d remembered my damn wallet. But hey, at least my clothes looked cute.


Here are some outfits and the fictional babes who wore them to their break-ups… (Idea reverently pilfered from Gala Darling, who’s written similar posts about first dates, New Year’s Eve, and dream girls!)

get it done

Nora wasn’t going to take any of his shit anymore. She showed up at James’ house with a box of his stuff slung under her arm, and kicked his door a few times with her steel-reinforced boot toe instead of knocking. She’d probably scuffed the paint. Fuck him, he deserved it.

When he opened the door wearing his plaid flannel PJ pants and nothing else, she rolled her eyes and thrust the box into his torso, knocking the wind out of his dumb face. “We’re done,” she barked, and turned on her heel.

“Why?” James sputtered. A Ninja Turtles action figure had fallen out of the box and he bent down to pick it up. “What did I do?”

“You know perfectly well what you did,” Nora snapped without turning around.

When she got back to her car, she caught sight of herself in the rearview mirror, all smudged eyeliner and mussed-up hair. She looked pissed, but she looked foxy. She dug her favorite lipstick out of her bag and reapplied it, slowly, carefully, with the precision of a woman who wants to look hot for the next chapter of her life. Once her lips were perfect, she revved up the car and embarked on a new adventure, joyfully Jamesless and unencumbered.

get it done 2

“I’ve always hated you in those glasses,” Jackson said when Audrey sat down at the desk next to his. “Don’t you have contacts or something?”

Audrey could feel their classmates watching her. Granted, lecture hadn’t started yet, so there was nothing else to watch, but the mini-drama of Jackson and Audrey’s Tumultuous Romance had been a key source of entertainment these past six weeks in Existentialism 101.

“I like them,” she said simply, beginning to unpack her notebooks and pens.

Jackson made a noise somewhere between a scoff and a snort, and that was the final straw.

“I don’t think I want to see you anymore,” Audrey muttered. And then, a little louder: “We’re just not a good match in so many ways. We disagree on the feminist significance of Simone de Beauvoir, for example.” She cleared her throat. “And I’m tired of writing your essays for you. You should do your own work; the rest of us do.” By this time, the other students were full-on staring. The professor had arrived, and seemed interested in this choice piece of information too. “Oh, and you’re an asshole,” she added with finality.

Gaping at her and leaning way back in his chair, Jackson lost his balance for a moment and spilled onto the floor with a clatter. Audrey wordlessly gathered up her notebooks and pens and moved to a desk at the front of the room. The lecture today was going to be about Dostoevsky and she wanted to absorb every word.

get it done 5

“I just don’t think I’m ready for this,” Jenny said with a sniffle. They shouldn’t have met in a park; the hillside was covered in grass and Jenny was allergic to grass. That was the only reasonable explanation for her watery eyes and nose. Right?

“It’s okay, princess,” Evelyn murmured, clutching her little one against her chest. “We probably rushed into this. I should have taken things more slowly. I’m sorry.”

Jenny shook her head and pressed her face against the older woman’s clavicle. She felt safe there, but it was a conflicted sort of safe. “No, it’s not your fault,” she stammered. “I’m just… not as ready as I thought I was. I’m still not over Mel. I should have been more real with you about that.”

Evelyn kissed the top of her princess’s head and held her tighter. “I understand,” she said. “I’ve been there before.”

They sat in silence for several long moments, Jenny’s wet breaths the only sound in the air. Then she said: “Can I keep my collar?” Her hand traveled to it reflexively, fingers hooking on the heart-shaped steel clasp.

Evelyn laughed softly. “Of course, baby. It’s yours. You can keep it even if you don’t think we should see each other anymore.”

Jenny exhaled deeply against Evelyn’s neck, her breathing starting to return to normal. “I might need it again someday,” she whispered. “You know, when I get over Mel and I’m ready to give this another shot.”

Evelyn smiled. The sun had started to set.

get it done 3

Alex had never hyperventilated in an airport before. Lots of other places, sure, but never an airport.

Sleepy passengers piled out of the arrivals door, fresh off a flight from Lisbon. Fuck, this is gonna be bad, Alex thought, but then, she always thought that. That was just how her brain worked.

She spotted Matt, weary-eyed with suitcase in hand, and a bolt of panic shot through her belly. Fuck, fuck, fuck. She had to do it. She had to. It was scary but she had to do it.

“Matt!” she called weakly, in a voice that was barely hers. He met her eyes, nodded, waved, and meandered through a crowd of chatty Portuguese tourists toward his girlfriend. She didn’t hug him immediately when he got close enough, and then it felt too weird to do it after that. Alex stuffed her hands in her pockets and mumbled, “Um, did you have a good trip?”

Matt started to answer her, but her jittery mouth cut him off. “Listen,” she rasped. “I gotta own up to something. When you were out of the country, I slept with someone else. And I’m really sorry. And that was really shitty of me. And you deserve better than that. It’s just, you were away for so long, and I got lonely, and I also started to think that maybe we’re just not – ”

“Just not meant to stay together,” Matt finished. “Yeah, I was thinking the same thing.” She looked up at him with those wide, blue eyes of hers. “And I slept with someone else, too,” he admitted sheepishly.

There was a silence before Alex let out a sharp bark of laughter. “Well! We really fucked this up, huh?” she declared with a grin. And then, taking his suitcase from him: “My car’s outside; let’s get you home and we can figure this out on the road.”

They were halfway to the parking lot when Matt threw his arm around her and ruffled her hair. “Missed you, pal,” he said, and it felt like a preview of what they could be to each other, someday, once the dust had settled.

  • I really liked the mini stories, even if they were about break ups.