The Practical Magic of Getting Dressed
A New York meditation on functional dressing, fashion week outfits and finding my personal style flow state.
As I sat and sulked in a restaurant in upper Manhattan, I did the only thing that made sense; people watch. Or more specifically, outfit watch.
I was in a funk partly due to a migraine pounding my head, but also because of FOMO — a feeling I’ve refused to engage in for many years. But I planned this year’s trip around fashion month, and it was hard not to feel like certain events, experiences were just out of reach while I was in the same zipcode. Along with that, I felt like I planned a lot of great outfits — perfect, even — for events, but none of them got worn to their potential.
But even with this rancid mood, the Upper West Side, nudged me awake. And as I took a painkiller and walked towards a breakfast spot, I thought about how there’s a beauty in being in a part of town where there aren’t really any NYFW events happening. As I glanced around, I realized there was an equal — if not bigger — excitement to see people’s outfits when they think no one is looking; when their number one priority is picking up their kids from school or running errands at the grocery store. It’s in those in-between moments where you start to see true style (and stories!) pop out.
So I sat down, gulped down some orange juice and a cold brew and watched.
Especially in New York, you can see such an abundance of stories within outfits. The line between practicality and performance become blurred into one. And yet, there’s this effervescent style that you can see emulate throughout people. Here, you can see style that is not only good but also cemented in, after years of movement and back and forth.
I also realized; there’s a big difference between New York fashion and New York Fashion Week fashion. And while I didn’t see much of the latter, I am coming home inspired by what I saw.
I think we often see the concept of practicality as something you need to adapt around when getting dressed instead of centering from the start. Or at least, that’s how it’s usually marketed to us from a “how to be stylish” perspective. But I think in fact, it should be something we lean into as a rule, not an exception. Because therein lies the intuitiveness of dressing.
Thinking about Allison Bornstein’s “wrong shoe” theory proves this — how our outfits can thrive through a comfortable sneakers or sturdy sandal, even if they don’t completely “go with” the main outfit. And I think it’s more than it creating contrast, it’s about the level of comfort that a “wrong shoe” may give you; allowing you flow into your outfit naturally.
As I watched people walk by, it was almost like I could see the friction of time passed, how everyone’s style is a result of so many steps taken, trains missed and errands finished. Life has been left behind on these sun dresses, velcro sandals and soft T- shirts. And the combinations feel fresh yet their own.
I especially liked noticing the style of older women — around my mother’s age or older. These are often women with the best style because they have the greatest gift — time. Wisdom has painted their outfits from top to bottom. I watched a woman in all black walk into the restaurant I was at. She wore a cowboy-style sun hat, a linen two piece set, black sunglasses and a bright pink, Vera Bradley-esque crossbody bag breaking up the darkness against her chest. And I couldn’t decipher if the decision behind that bag was stylistic or practical. But I’ll never know, and that’s the best part.
I think that’s why there’s always been such an adoration for photographing street style. The subjects’ personalities and who they are reveal themselves in small glimpses. The full motivation behind the outfit is unseen, only hinted at slightly, and it’s up to you — the outfit watcher — to play the guessing game. Not for any rewards at the end of cracking a code or dissecting a reference; but just for a chance to know a stranger a little more.
A big part of fashion week is knowing. Or at least, it’s about finding out. Analyzing. Decoding. Every group of looks is often reacted with a set of questions: Why did they pick this fabric? Why did they stitch it like this? Why did they use this cut? Fashion critics sometimes are at odds about finding out the true theme of the designer’s art — you see this in the literary, art and food world as well. But sometimes it’s just as simple as it feels good — it tastes good, it reads good. It scratches a human itch that is comfortable and easy. Sometimes, if you don’t have to convince yourself it’s good, it probably is.
People are also shocked when designers give a simplistic answer to these questions. Sometimes there’s a story in their head that they poured into the garment, other times there’s room for interpretation — a narrative that may be written by the wearer. And maybe it’s because designers, like many artists, feel like they make their best art when they’re in that flow state; moving forward with each thread, each stitch and hem.
I’ve always wondered why the last couple years I’ve come to New York, I felt so comfortable and at ease with my style. You would think because of imposter syndrome and the silly pedestal some of us non-New Yorkers put on this city, it would be the opposite.
But I think it’s because the city forces me to embrace my intuition. It’s because I always prepare with practicality in mind; what makes me comfortable, what makes me feel at ease, what will make me flow through this city without worry. It’s the biggest fashion city in the U.S. so of COURSE I want to look stylish, but even still, that comes second to practicality.
And this often translates well when I get home because I always strive for my style to looked lived in. Even if I just bought a brand new outfit and wore it out of the store, I want to wear it with enough ease and confidence that suggests I’ve owned it for years.
And now, I come home with these items having new life — partially because I repeated them so much! This has happened with other clothing I had brought to NYC in past trips. They have become worn in and storied in a new way. For example, from the last two Octobers: a Vince Camuto sweater, my mothers black ‘90s scort and embroidered suit vest. This last trip my trusty side kicks consisted of my Everlane tank tops (in three colors; navy, brown and white), my Wilfred Aritzia shorts and my black and white Onitskuka Tiger Asics.
These items now make my future outfits with them injected with more magic. Look what i’ve done so far in them! Look at what they’re holding onto!
Being able to write a story into your garments is the biggest key to personal style.
I watched as two girls in flowing sun dresses walked by, flared in the right places and covered in florals reflecting a church courtyard garden. Paired with easy, white sneakers and no purses (probably for a specific reason), they walked with ease, focusing on each others conversation — relaxed posture and leaning their heads back to laugh. No fuss, no adjustments, not even one hand on the garments they wore. Instead, the dresses just hung there, while the they lived their lives.
And maybe this effervescent style secret sauce that I was seeing on the streets in front of me had more to do with the attitude, cadence and rythym in which we move our bodies than the garments themselves.
A young girl, about 10, walked passed me with a backpack. She wore a pair of jean shorts, an easy T-shirt and black and white, slightly oversized striped sweater on top. Plus, a purple pair of glasses. And even though she has so much left to learn in life, in that moment, I think she had more confidence in her outfit than I did in mine. Another girl — in her ‘20s — walked by with a clean, slicked back bun, sneakers, white socks, a sports bra to combat the heat and a nearly comoically loose pair of shorts. I almost wanted to jump into her outfit then and there.
In my most recent post,
echoed this thought I had in response to my question: “What is your outfit building process like?” She said:“…One of my rules of thumb is to never wear an outfit that you have to adjust. I essentially wear outfits that are like, the outfit version of a slicked-back bun. I do not want to feel like I'm constantly adjusting anything.”
So maybe whatever I’m referring to — this practical magic — of dressing is about simplicity. Maybe it’s about ease. But I don’t think it’s about effortlessness. Or about is minimalism — at least in the way the concept has been sold and delivered to us.
Maybe this ties into not only intuitive dressing — something that TikTok creators Sydney Greene and Tiana Gidley have talked about a lot — but also mindful dressing. I think it can be argued that your outfit serves you best when you don’t notice it — just like going into a flow state with your favorite hobby serves you best when you aren’t overthinking it. It’s when you’re able to move through life with enough confidence that it doesn’t distract or contradict you from your sense of being.
As my own style becomes more cemented in, I’m realizing that the most stylish people I look up to aren’t the ones who have closets, accessories or even outfit formulas I want. No, instead I want their sense of self-assuredness. I think about this with the one-and-only,
Hurst (@pigmami) who puts a lot of effort, thought and planning into her wardrobe and clothing purchases (case and point: this isn’t about effortlessness!) But the way she rewears, moves and expresses herself in her clothes — makes it so desirable. It feels (at least to me) like with all the process she puts into her wardrobe, when she’s out in the world, it all melts away and she’s able to exist.
And I think we need to admire that more in the street style we see — both on the streets in front of us and online. As much as I love a good outfit formula, we should make sure we’re not becoming too formulaic with our dressing — where we become lost and frusterated when the right equation isn’t able to be copy and pasted.
So often, I see a creator sharing their outfit online and someone in the comments is asking — begging! — to give them a step-by-step tutorial on how they too, can style a T-shirt and jeans. And I don’t mean that to come off snarky because this isn’t the commentator’s fault! It’s the fault of the hyper-consuming world we live in, the paradox of choice, the over reliance on fashion influencers and so many other factors.
Of course I admit, a lot of the NYFW, PFW and CPFW outfits that come out every year are some of my favorites to reference and find inspiration from. But taking note, I always feel more inspired by people re-wearing pieces from their closet or styling vintage pieces in a new way. If it feels less performative and more like they’re leaning into a new version of their style, instead of relying on brands or trends.
To me, it’s about more than just being (and looking) comfortable, it’s about allowing enough life to come through the seams.
I think we’re sometimes afraid to lead with practicality in our outfits because we’re afraid we won’t be showing our personal style enough. Which I think in itself, is the wrong way to think about it. In fact, maybe it shouldn’t be something you’re thinking about too much at all. Because this makes it a set of rules that keeps you caged in a way where you can’t explore, and more importantly, can’t move.
And I think what we forget is that leaning into practicality allows you to feel your personal style more. The soft silk of a simple slip skirt against your legs as you walk four blocks, a jacket that fits perfectly on top of a slightly chunky sweater (can you tell I’m salivating about fall outfits already?), or a pair of worn-in sneakers that feel like melted butter on toast as you slip them on.
One of the most stylish people on TikTok, Evan Smith, said it best: “Not every day needs to be a slay.” Because I promise you, even if you don’t think it is, you may walk by a sad girl eating her breakfast who becomes suddenly inspired not just by your clothes, but how you’re wearing them.
This was such a great read, I love how you interpret personal style!
❤️ ❤️