Does being fashionable mean being fashionable allllllll the time? I’ve been pondering this question since August, when I was visiting Copenhagen for fashion week. After four days of curating what I would consider thoughtful outfits  — ones that demonstrably expressed the nuances of my personal style and communicated that I am a woman who cares deeply about clothes and their potential as creative fodder — I got dressed for the airport. I put on black leggings, a white tank top, a patterned sweatshirt I didn’t particularly like, thick white socks and grimy running sneakers. I then skulked down to the lobby of my hotel, intending to spend a quiet couple of hours exploring the city on my own before heading out to catch my flight home.

As fate would have it, though, I ran into another person from my press group — the editor-in-chief of a prominent online fashion publication — who, knowing we both had time to kill (her flight had been canceled and mine wasn’t until later that evening), asked if I wanted to go get lunch with her nearby. I did! I really, really did. Except I also wanted to crawl into a hole, sleep for 700 years and emerge reincarnated as someone wearing an entirely different outfit.

We ate lunch and spent the afternoon walking around, popping in stores and soaking in the unseasonably warm Copenhagen weather. It was perfect and lovely and exactly what I wanted to be doing on my last day, and yet, I couldn’t stop thinking about what I was wearing. I gnawed on my shame like a bone, suppressing the urge to assure my companion that I knew my outfit was bad, that I was only wearing it because I was about to sit on a plane for eight hours, that I normally dressed much better. (I was simultaneously aware of how silly I was being, and how little her interest in having avocado toast with me had to do with whether or not I was wearing a spectacular outfit, but that rationale did nothing to ease the spiral).

Physically comfortable but emotionally tender, I spent the plane ride mulling the aforementioned philosophical inquiry: Does being fashionable mean being fashionable all the time? In theory, I firmly believe the answer is no. There are no constraints on what it “means” to be fashionable, because defining it is such an innately personal undertaking. In practice, however, I’ve always been mesmerized by people whose personal style is consistently, outwardly evident (even when they’re at the airport, even when they’re taking out the garbage, even when they’re sitting on a park bench reading a book). I want to be one of them. I want to be the kind of person who crafts a casually appealing ensemble before heading out to get coffee on a Saturday morning. I want to be the kind of person who goes to pick up a prescription at CVS dressed in an outfit I would be proud to run into Chloë Sevigny while wearing. In my heart of hearts, though, I know I am not. I’m inherently too lazy, too devoted to comfort, too rebellious against my own self.

I’m working on building a relationship with myself that is less dependent on what other people think.

A few weeks ago, I woke up before my alarm on a Friday and decided to take advantage of the extra time with a grocery store run. I changed out of my pajamas and threw on what I call my “house dress” (basically a T-shirt that reaches my knees), an oversized jean jacket I stole from my mom and rubber sandals. I didn’t like the ensemble that resulted (at all), but that wasn’t the point. I reached for these particular items because they were easy and comfortable. The possibility of running into someone I knew didn’t even occur to me, but once again, the universe interfered. I encountered not one but two industry friends when I stopped by Cha Cha Matcha for a pre-grocery store caffeine jolt. Before I could catch myself, I apologized to both of them for having the nerve to dress so abysmally in public, and then immediately regretted drawing further attention to it. The very apparent reality that neither of them cared was besides the point. As much as I am fulfilled by my relationship with style, it was devastatingly clear to me, in that moment, that I am also minimized by it.

If you sliced me in half like an apple, you would see two distinct sides: the side that cares so much about how others perceive my sense of style that I feel like a less worthwhile person when I’m not engaging with it in an obvious way (particularly around people who don’t know me that well), and the side that shouts, “WHO GIVES A FLYING FIG?” into my stack of sweatpants. The latter shows no signs of dissipating, nor do I think it should, so I’m trying to examine the former more critically. When I spend time putting together an outfit I love, I’m doing it for the occasion, and for the people I want to see me in it. Is that taboo to admit? That even though I enjoy getting dressed up, I don’t really do it for myself? Whether it is or isn’t, I’ll willingly acknowledge that the bulk of enjoyment I get out of wearing an outfit I love is predicated on it being seen and appreciated, but I don’t think it’s healthy that my self-esteem takes a hit every time someone glimpses my proclivity for off-duty non-outfits.

Being fashionable does not mean being fashionable all the time. I know that logically in my head, but I’m still working on knowing it intrinsically in my guts. I’m working on building a relationship with myself that is less dependent on what other people think, that holds my fashion sense and my intelligence and my interestingness as fixed points instead of variables that increase or decrease based on my experiences on any given day, because ultimately, choosing to opt out of the effort it takes to put together a Look with a capital L on occasion doesn’t revoke my personal style card. It just makes me human.

Photos and collage by Edith Young.

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