The skirt I can't seem to say goodbye to

And so I am writing about it.

It’s September or October of 2009. I’m in my first semester of college in Baltimore, MD.

My friends and I take a shuttle¹ — one that serves the colleges in the area — from our campus to the stop that serves the art school. We’re on a mission.

We’re going to a thrift store.

It’s shocking to me, in the moment I’m writing this, that this took place almost sixteen years ago. College doesn’t feel like it was that long ago. I still think it’s within my reach, but the reality is I’ve lived a lot since then.

But, almost sixteen years ago, I took a shuttle into the city with a group of friends. There were somewhere between eight and twelve of us, though I can’t remember exact numbers. I don’t remember much else — I know we perused a thrift store that, sixteen years later, is no longer standing. I know there were multiple windbreakers and flannel shirts and a few pairs of boots purchased by a few people in our group.

And I know I walked away with a bag of treasures — one of them was a red, floral skirt. I paid $3 for it.

I didn’t think much of the skirt when I bought it. It’s a calf-length, Coldwater Creek skirt from the 90s. I wasn’t really into long skirts then, but I figured I could belt it and wear it as a dress. I was more excited about the flannels, boots, and t-shirts I bought that day.

While some of the clothes I bought that day became early closet staples, the skirt lived in the back of my closet for a few years. Sometimes worn as a dress, but other than that not seeing much light amongst other competing articles of clothing.

Still, I held on to it. When I would donate and give clothes away to friends, I always held onto that skirt. I loved the idea of it, even if I couldn’t figure out how it fit into my wardrobe.

At some point between my junior and senior year, I started wearing that skirt more — first, as a dress, but then experimenting with it as a skirt. I had thought it was cool ever since I bought it, but I also finally enjoyed wearing it. I had started adding more and more florals to my wardrobe, and it seemed like that’s what was needed for the skirt to cement its place in my life.

I wore it on the first day of classes my senior year. Midday, I got an email about a job at the Apple Store that I’d applied for. The store was in the mall next to campus, and they were hosting a group interview later that day. I looked at my outfit: my $3 thrifted skirt, a pair of Birkenstocks, a sleeveless white button-down that I tied at the waist, and the pen-and-coffee-stained teal JanSport I’d had since my senior year of high school.

“This doesn’t feel like appropriate attire for an interview,” I said to my friends, panicking. We had just gotten out of class and the interview was in an hour. “I don’t have time to change. Should I tell them I can’t go?”

My friends told me I looked fine and convinced me to go anyway. “Maybe you can tuck the shirt instead,” one of them offered.

I initially agreed and tucked the shirt in, but on my walk over I tied it back the way it was. The outfit didn’t feel natural with a tuck.

Long story short, I got the job and ended up working at that store for four years — that is a story for another day, though. This one is just about a skirt.

That was the first moment I really remember that skirt becoming a staple. At my Apple Store job, I found pants and skirts to be a fun way² to express myself while wearing the famous blue t-shirt.

For a while, the outfit was the same: red skirt, Birkenstocks, and a sleeveless button-down. As the weather got cooler, I added a cardigan. And then as the weather got even colder, a pair of boots, tights, a circle scarf, and a big jacket.

Not the skirt, but a similar outfit you might find me in.

I found a similar skirt in blue that I bought and wore a lot that year too. And at this same time, floral started to become more and more ‘in vogue’ (at least amongst a certain type of person). I found myself embracing florals more and more, until I became a ‘floral dress’ person. There are a lot of memes and jokes about the era where people were dressing in business casual to the club (and bar), but I was among the group that would throw on a floral dress and call it a day. We don’t get a lot of coverage on TikTok, but we existed.

my floral collection, circa 2013

My style evolved, but that skirt became a constant. I wore it a lot my senior year, and in the years that followed. It was perfectly light and breezy, especially when the heat in Baltimore made it difficult to exist, but I could also wear it year-round with a pair of tights. I wore it with a variety of shirts and brought it out for most occasions.

I wore it to work, to hang out at the park, to go food shopping, and to my favorite bars — whether I was just sitting around with friends, dancing to Bell Biv Devoe’s Poison at ‘Two for Tuesday,’ or enjoying a victory with my trivia team, the Picklebacks.

When we moved to the Bay Area in 2016, I got rid of a lot to prepare for that move. Furniture, books, crockpots, and larger items, but I sold and donated a lot of clothes, too. But the skirt never even made it to the ‘Shop my Closet’ Instagram account I made. It found its way into my suitcase and settled into a new life on the West Coast.

I still wore it, but the floral trend had passed, and while I still held on a bit, I found myself gravitating to simpler patterns and the allure of Everlane.

One day, in 2018, I’m packing for a trip back to New York. I see the skirt in the back of my closet and toss it in my bag. The weather looks hot while I’ll be there.

I end up surprising myself and wear it three times during that trip. Is it the humidity that draws me to it? Or the fact that I was spending time with people I went to college with, and therefore found myself nostalgic for those times and who I was during that period, and the skirt made me feel like I was back in college again?

After that trip, I found myself grabbing the skirt more often than I had been. I was even photographed for a brand campaign at my old company wearing it.

the trip that renewed my love of the skirt & the brand campaign

When I moved back to the East Coast a year later, I had another opportunity to purge my closet and ended up donating a few bags’ worth of clothes — a few pairs of Allbirds I didn’t wear anymore, some leggings I didn’t like, some sweatshirts, t-shirts, etc.

And still, the skirt found its way back to Brooklyn.

In the summer of 2020, it had its resurgence. Being back in a more humid climate, coupled with a desire for effortless styles during a time when I wasn’t doing much (except sitting outside), and again living near friends from college, made for a perfect formula for its comeback. And so for the next few years, it became another summer staple.

In the summer of 2023, when I was pregnant, I tried to throw it on, but it didn’t sit right — it looked strange sitting below my belly, and was too tight to sit above it. So it was stashed again.

I tried it on postpartum, at the end of the same summer, but even that felt too restrictive.

And since then, I just haven’t been feeling it. I don’t know if the style feels too young or if it belongs to a different version of myself, but every time I’ve put it on recently, I’ve been itching to get out of it. It’s not physically itchy — still comfortable, still breathable, and still technically fits my body. It just doesn’t feel like it fits who I am today.

Just last week, on a day that hit 97º (which I ordinarily would’ve jumped at the chance to put this on), I tried to wear it to drop off my son at daycare but found myself annoyed to be wearing it; adjusting and pulling on it as I walked those eight short blocks (round-trip). I changed immediately when I got back home and stashed it in my closet.

A few days later, I went through my clothes again to donate (and perhaps sell a few, if I find the energy). I was able to gather five trash bags of clothes to donate and three FreshDirect bags of clothes I might try to sell, but might end up keeping too. Even with the memory of how quickly I needed to take it off last time, I still wasn’t able to make a decision about the fate of the red skirt.

Live footage of me asking myself, “does this bring me JOY?”

At the top of one of the FreshDirect bags sits the skirt. I haven’t made up my mind yet — part of me thinks it might be time for us to part, but another part of me can’t bear the thought. It would be admitting that my 20s really are behind me, that it was closer to twenty years than ten that I started college, that while I’m still the same person, there’s a lot that has changed. And I find that hard to admit.

I find it hard to admit that my ‘formative years’ are perhaps behind me, and that they have been for a while. I find it hard to think of a time when, next summer, I reach for that red skirt and it’s no longer in my closet because of a decision I made in haste.

This skirt has seen me go through friend shifts, career changes, romantic partners, hobbies. It has lived with me in three different dorm rooms and eight different apartments (nine, if we count the apartment my parents lived in when I was in college). It has traveled to over a dozen cities, many of which are abroad. It feels integral to me growing into myself as an ‘adult’, and yet I find it has no place in my wardrobe now, arguably the most adult I’ve ever been.

the skirt, throughout the years

It doesn’t take up much room, and I think that’s why I’ve held onto it until this point. It can sit neatly on a hanger, sandwiched between other articles of clothing, waiting to be worn again.

I find it difficult to even follow the advice of Marie Kondo³ and find myself coming up blank when I ask the question: Does this skirt bring me joy?

I no longer feel joy wearing it, at least not recently, and not in the moment. But I feel joy looking at it, touching it, remembering. I feel joy trying it on, but just not in wearing it for long periods of time. So what’s one to do with that?

From what I know about Marie Kondo, she’d probably tell me to thank the skirt for the joy it did bring me and send it packing.

I’ve done this exercise multiple times — I first learned about Marie Kondo and her ways when I was living in Baltimore, gearing up to move to the opposite coast, and it served me well. Usually, I find the answer to whether or not something brings me joy to be quite obvious. And each time I’ve held up the red skirt before, the answer was a resounding yes.

But now, the skirt is caught in a bit of limbo, and I have trouble discerning whether the joy it brings me is only rooted in memories, or if the tactile relationship I have with this object still holds significance (spoiler: I think it might). It’s causing no harm in the back of my closet, or sitting at the top of a bag, right?

I’ll go through the exercise of combing through the FreshDirect bags, trying to dig into whether each of these items brings me joy. And I expect to get rid of a lot of what’s in them. And I expect to take that skirt and put it in a ‘donate’ bag, only to pull it out a few minutes later (which happened three times last week, mind you).

I expect my husband to see me doing all of this and ask if I’m finally getting rid of “that ugly skirt” (he’s never been shy about his feelings about it, but I guess neither have I).

But I don’t expect I’ll get rid of it this time around. Maybe I’ll quietly list it on my Depop, but at a price that’s so unreasonably high, it’s basically a dare. But even that feels too risky. What if someone does buy it? Am I ready to say goodbye forever?

I’m not going to sit here and say that a skirt taught me huge lessons about the human experience, but I figured I’d write it a love letter instead. To thank it for everything it brought me: the memories, the style choices, and for being a great use of $3. Part of me expected this to bring a surge of closure, but at this exact moment, I still am uncertain of its fate.

1. Shout out to the Baltimore Collegetown Shuttle

2. And fun collars, too! Although the rules have since changed, you can no longer have a fun collar popping out of your shirt.

3. If you have been living under a rock for the last decade, Marie Kondo is a home organizer. Her famous method helps people get rid of what no longer sparks joy. https://konmari.com/