My Relationship With Clothes Is Changing in an Unexpected Way

I have cared deeply about what I wear for as long as I can remember. At around the age of whatever age it is where you’re able to dress yourself but still required to wear a diaper, I — according to family folklore — stood at the top of the stairs one morning, late for a much anticipated playdate, and screamed at the top of my lungs that I couldn’t leave the house because my outfit did not match.

I remember again, at age six or seven, that I felt wholy unroyal during a game of Pretty Pretty Princess because I didn’t like what I was wearing. The next time I went over to the game owner’s house, I made sure to dress for the occasion (in biker shorts and frilly lace socks), just in case another opportunity presented itself.

There was the family trip to Disneyland when, on day one, I didn’t feel put together — odd thing for a kid to consider, I suppose. But either way, as a result, I thought carefully about my day two outfit so that I could enjoy myself without distraction going forward.

There was the fifth grade Halloween dance, when I showed up as Groucho Marx because I thought it would be funny. It was and it wasn’t; I realized upon arrival that all the other girls had gone “sexy,” so I ripped the mustache off and tied my shirt at the waist to try and salvage it.

Once, in my early twenties, I brought two pairs of shoes to a party because I couldn’t decide how I’d feel about my outfit upon arrival.

I could keep going. My list of these anecdotes is long. I could write a graduate-level dissertation on all the times I wanted to go home and change because I didn’t feel “dressed enough,” and another of all the times I did, to much relief. But it was always less about the style, or the fashion, than it was about quieting the part of my brain that gets noisy when it senses a visual misalignment between myself and the event at hand. (I’d call myself “aesthetically sensitive” if I didn’t fear a kick in the shins, though the underlying sentiment is probably true; I am in no way versed in interior design, but I’ve left restaurants because they looked a certain way that made me feel unsettled.)

It was always less about the style, or the fashion, than it was about quieting the part of my brain that gets noisy when it senses a visual misalignment between myself and the event at hand

What’s strange is that, recently, I’ve been deliberately eschewing the whole business. I’ve almost become resistant to caring so much about what I wear, as though to prove a point to myself, and I don’t know where it came from.

I’m not including weddings or work in this, but at the start of summer, around high “going out” season, I could not bring myself to get dressed up like my friends. They wore cute new tops, pretty shoes, skirts and dresses. They added earrings and baubles and bangles and all sorts of fun things — the things I’ve always loved, that don’t just decorate me but used to help decorate my overall experience of an evening. During the day, around water, I watched as surrounding women wore big brimmed hats and cat-eye sunglasses and adjusted charm bracelets around their ankles. Their swimsuits, frilled and colorful and statement-making in their own rights, were just half the outfits when you looked at the sandals, the bags, the towels, the coordinating cell phone cases.

In various versions of both situations, I wore denim cutoffs and a white tee, with dirty espadrilles at night and Birkenstocks in the morning.

Same thing back in the city. If I was meeting friends on the weekend for a late breakfast, no matter how “cute the spot,” no matter how dressed I knew my friends would be, I’d wear gym shorts and a sweatshirt. It wasn’t “effortless,” it was borderline sloppy. The opposite of my previous obsession with looking put-together.

There’s nothing wrong with Birkenstocks and sweatshirts — wear what you want, I always say. But I guess the rub for me is that in these instances, I wasn’t in love with what I had on. None of it made me feel like a better version of myself. Some nights I felt like I’d shorted myself. Some days I felt embarrassed upon arrival, suddenly aware of how lazy I must seem. But mostly I was neutral, indifferent. Happy to have nothing to document for Instagram. Not there to hide against the wall, but certainly not there to impress anyone either. And this, for the first time in…maybe ever…felt more comfortable than my former alternative.

In a story we recently published on the psychology of overdressing, I said that instead of leaning toward dressing under- or over-, my preference is always to feel “appropriate,” a comfortable nestling space that allows me to harmonize with my surroundings and those around around me. It’s why, though I like to feel special, I’ve historically fallen in-step with my friends where pants versus skirts at night are concerned. It’s why I will hound you for deliberate instructions on your holiday party’s dress code — so I can make sure that, once my personal taste is accounted for and satiated, I’m not stepping on anyone’s toes. It’s always been less about standing out or fitting in for me as it’s been about centering my equilibrium in the world at that moment. Where you may get anxious in a messy room (though I do too), part of what helps to anchor me is just the right combination of jeans and blouse. Or the right T-shirt at Disneyland. Perhaps this is why I’m even noticing my recent lean toward dressing down amid the status quo.

Am I just feeling lazy? Am I subconsciously protesting the tap-for-credits culture in which I’m immersed and partake, the social media swimsuits that I too buy, the constant (self-inflicted) pressure to be camera ready just in case my friends want to take a photo?

Or am I putting myself in neutral in anticipation of some sort of larger change?

They say you’re supposed to dress for the job you want; I get the psychology. A sartorial self-fulfilling prophecy. So maybe without realizing it, whatever the impetus, I’m dressing for the state of mind I need. Maybe I’m craving simplification in an over-maxed, hyper-stimulating world of pings and dings and Fashion-with-a-capital-F and “for Instagram” outfits and pom poms. Maybe I just need one less thing to do, and getting dressed is an easy thing to cross off. Or maybe I’m entering a new phase of my personal style, of my personal self. Maybe this is all a part of my favorite topic: growing up and getting older. Is this the final stage before I fully come into my own? Do I even need these questions answered?

Should I just put my shoes on and come downstairs already?

Amelia Diamond

Amelia Diamond

Amelia Diamond is a writer, creative consultant, and Man Repeller alumnus living in New York City.

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