Packing as snapshot of self

The concept that haunts me, rigidity, and letting go

This week’s newsletter is inspired by a question from writer and DRESSED reader,

Heather

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What should I pack for a three-week long trip? Should I bring more neutral pieces (like my white sneakers) versus pieces that are more fun and still functional, but that go with slightly fewer thing (like my green sneakers)?

I once read that you should be able to pack your entire wardrobe into a suitcase and it all go together. The idea being that everything you own is cohesive. I don’t remember who said it, where I got it, and I’ve probably altered the quote, but it stuck with me; a filter for curating your closet—and yourself.

A decade later, I still think of this concept when I’m deciding whether to add something to my wardrobe, but less rigidly than Robyn of years past. I see this progression in the suitcases I’ve packed, the outfits I’ve worn, for trips in my early twenties, to those in recent years. Packing being a snapshot for a specific moment in time; who I was, how I was feeling, who I wanted to be.

I packed for my first big adult trip when I was 23. My then-boyfriend’s parents invited us on a two-week vacation throughout Southeast Asia. I was a year-and-a-half out of college, living in New York City, and very much concerned with “getting it right” in all aspects of my life, including my wardrobe.

I was reading a lot about style, seeking advice from women in their thirties on how to spend the $20 an hour I was making as an assistant for a few execs at the now defunct Time Inc., one tidbit in particular standing out to me: a woman buying a pair of fancy pants each year so that by the end of the decade, she had a wardrobe full of staples. I liked this. It was like saving for retirement, but with clothes. I’d never heard of the brand before, Joseph (now, whenever I hear or see the name, I think of baby Robyn), and I couldn’t afford to purchase their pants anyways, but I used the story as inspiration.

I became fixated on acquiring wardrobe essentials—which were pieces other women had deemed essential—identified through their having lived some life and allowing their tastes to develop. The perfectionist in me thinking I could skip what I perceived as the awkward stage of self-exploration, and get straight to the chicness, if I tried to emulate the women I admired.

There were lots of “perfect” tees, a couple camel coats, the leather pencil skirt, and the leather pants, the knockoff Celine Luggage Phantom bag—pieces that I still stand by, but were like playing dress-up because they were an idea of who I thought I should be, instead of who I was, where I was going.

I see it in the photos of me from this trip. Like the outfit I wore to climb the Great Wall of China, a decade ago tomorrow; those black leather pants, tan strappy sandals, gray t-shirt, tan trench coat, and vintage Fendi sunglasses.

All but the coat are gone. I don’t really like it, but I keep it because it was something I asked for on my 21st birthday. I wish I still had the sandals, they bit the dust years ago, and I loved the sunglasses, but I lost them on a trip to Austin in May 2022.

It wasn’t the most practical outfit—I had no idea how steep the steps would be in some sections—but I’d worn it, I’d packed it, because I wanted to look chic. I wanted to look back on those photos and think, “wow! 23-year-old Robyn had style.”

Instead, I look at the me there tenderly. She’s trying so damn hard. If only she would try a little less. Trust that if she let’s go, the magic will happen. It’ll take some time, but I’ll get there.

There are moments when I wish I’d started relinquishing this control sooner, thoughts of “where would I be now?…,” but then I’m reminded of something my friend Mel recently said in our group chat:

“…we think all humans live on this templated timeline…but we are souls on their own journeys and some of us just have more meandering paths or longer paths for various reasons and that’s perfect for us and what we’re here to learn/heal.”

Well world, here I am, on this meandering path ~

I started taking photos of what packed after I turned 30. This wasn’t a conscious decision, but I now see it tied to documenting my exploration of self; I was starting to pull back the layers of shoulds, thinking about what I wanted, who I wanted to be, instead accepting the predominant script as fact. You see it in the clothes I wear on my later trips. I’m letting go of the rigidness and allowing myself to follow the breadcrumbs, as my friend Antoinette would say.

There are the colorful clothes I rented from my friend Jo’s business OpenClosit for a trip to New Orleans in May 2021, the first solo vacation I’d ever taken.

For this trip I wanted to feel both myself, and outside of myself, going to New Orleans, a city I knew well from college, but staying in a neighborhood that I’d never explored because it was a pain to get to in those pre-Uber days, and wearing bright, patterned dresses and sets that juxtaposed with my usual staples of button-ups and jeans. I threw in a pair of lace gloves at the last minute and wore them to dinner with my friend Danger, and later, walking along the Mississippi River, feeling magical.

Then the things I packed for a three-week trip to Mexico City in August 2022, featuring the last-minute additions of my sister’s long white dress, which she’d later give to me, and my white Labucq boots that I bought at a consignment shop in 2019, that my brother now lives next to, five years later.

I didn’t wear the red vintage Emanuel Ungaro jacket that I had made into a dress, and had a hunch going into the trip that I wouldn’t, but I packed it anyways because I like how it looked hanging with my other things, and also—you just never know.

More recently, the luscious fabrics and form-fitting pieces for a trip to Riviera Maya, Mexico for my friend’s bachelorette in August 2023.

I look at these photos and they make me happy because they represent different parts of my being. It’s not this one definitive style, one dimensional self, that I had previously packaged up. The clothes decidedly more “fun and still functional,” and that’s what makes them such a delight. Even the black, white, and browns of the Riviera trip—they’re all neutrals, but there ain’t nothing basic about them. We’ve got sequins! and satin! and leather! oh my! (plus some spandex, cotton, crochet, silk, straw, and linen).

and so Heather, pack those green shoes. They may not go with everything, you may just wear them once (or not at all), but that’s not the point. They add that pizzazz, that little something-something, that reminds you your you—the woman who bought the fun sneakers in the first place, because they made you feel something, and that’s what we want when we’re traveling—heck, in our everyday life too. I look forward to seeing where they take you.

Xx,

Robyn