Dress Your Family in Chelsea Boots and Introspection

On the importance of not being who you think you are.

I’ve spent the last 45 minutes figuring out what I’m going to wear today.

“Going to” is a key phrase, because it’s already 3:15 pm, which in the murky-gray winter of the Pacific Northwest counts as dusk, and the furthest I’ve moved is to the front porch to pick up my mom’s FedEx package. But now here I am, Googling things like “what to wear with light wash jeans” and “t-shirt under v-neck sweater?” for the first time in my life (re: the latter, Ashley Weston says absolutely not).

This is my third day at home, and getting dressed has taken at least this long every morning since I got back. I’ve been leaping onto bathtub ledges for full-body views, prying open long-sealed boxes of old cardigans, furiously buffing out scratches on shoes I stopped wearing when I was 17. Yesterday, I forced my parents to let me open a pair of chelsea boots I knew they bought me for Christmas because I couldn’t figure out what to wear with my pink chinos.

My last boyfriend used to do a streamlined version of this on weekdays, asking a half-asleep me to decide between the white Keds or the brown boots, whether he needed a scarf, if the ripped jeans would be too much since he might run into that one English professor he really liked on the way to French class.

I was dismissive of his anxieties in what I thought was a loving way: “It all looks good,” I’d grumble, glasses still on the nightstand, and I wasn’t lying — he knew how to dress far better than I did. There was something else going on though, too; I thought that by telling him he looked good no matter what, I was committing a revolutionary act against the very notion of negative body image. I was on a mission from God to deliver him from consumer-driven beauty standards and to plant rapidly-growing seeds of self-love that would follow him into the next life.

Mostly, he just found it annoying, which it was. He was asking me a question, he wanted an answer, and my virtue-signaling was both self-serving and kind of invalidating. He cared about how he looked, and caring about how you look is not always tethered to a crisis of self-image. I cared about how I looked, too, but I never asked these kinds of detail-oriented questions, which is why if you dig far enough back in my tagged photos on Facebook, you’ll see a lot of bright-red denim and more novelty Elvis jewelry than you’re likely to find in a strip mall pawn shop.

I entered that relationship with a lot of underdeveloped but etched-in-stone notions about the kind of person I was at 20. In my head, I was admirably unburdened by the way I looked. I was always kind. I may, in hindsight, have been depressed in high school, but I decided that putting 3,000 miles between me and that version of myself was an effective reset button. Above all, I was ready to let someone else in.

My therapist and I like talk about how I try to leap over mistakes before I’m allowed to make them — how I assume I’m at the end of a process before I’ve had enough substantial life experience to help me reach a conclusion. I want to Know How It’s Done and pull it off before I even know what the wrong version of whatever I’m trying to do might look or feel like. This, as you can imagine, makes it really tough to learn anything.

Over the course of the relationship, I was met time and time again with evidence that I needed to reconsider, to adapt, to understand that I was holding fast to these pillars of identity to make up for a lack of experience. Instead, I proudly dug in my heels and insisted that I Was The Kind Of Person Who Had Figured This Out Already.

After a lot of hemming and hawing that isn’t very interesting or productive to rehash, we broke up. Again, I decided what kind of person I was based on a nonexistent dataset: the kind who stays friends with his ex. Dan Savage said it was a good idea on his podcast and I was obviously a patient, understanding person. Bridge-burning was for people who didn’t Get It like I did.

It didn’t work out. It’s been months and I still don’t have the emotional energy to conjure up imagery that might describe what it felt like when I realized there was no friendship left. A million Tumblr users have done it before me, and I used to ridicule them for it, but now I understand that clichés are clichés because there’s nothing clever to be said about undiluted emotional pain. Subversion is an intellectual luxury afforded to those whose minutes aren’t being devoured by heartbreak.

The important lesson was this: I had experienced a real failing of my expectations that cut against the portrait I’d painted of myself, and at this point, there was no denying it. I wasn’t going to stay friends with him. I wasn’t as measured as I thought I was. “Letting someone in,” it turns out, is the cumulative effect of a million other tiny successes rather than an action unto itself, and turning a throwaway question like “what do I wear” into a moment for proselytizing about the dangers of vanity is pretty counterproductive to the process.

So finally, I started to consider whether my convictions were actual traits. It’s a scary thing to do, and I don’t blame myself for taking until now to press play. Interrogating deeply-held beliefs is hard because most of the time, it feels like a yarn ball that might never stop unraveling. You have nearly unlimited permission to second-guess yourself once you admit you were off the mark the first time. If you were wrong about the kind of person you are in relationships, then are you wrong about the fact that you really like Joni Mitchell, and why did you feel the need to be so vocal about that in the first place, and oh my God, wait, did you even need to move so far away or have you accidentally isolated yourself to avoid dealing with your problems???

Eventually, though, you find solid-enough footing, even if the process of doing so forces you to acknowledge that the ground will probably shift again.

I’m trying on a lot more new hats than I was a year ago. I’ve found myself less ready to speak in conversations because I’m more aware of why I’m saying what I’m saying, and it’s disorienting, but it feels right. Ultimately, I know I haven’t put my sense of self through an office shredder; there are certain constants to my personality that a sizable blow to the head couldn’t shake at this stage in the game. Instead, I’m in a careful recalibration process that might mean I stop pretending to like writers I’ve never heard of and don’t Snapchat every IPA I drink.

It also might mean that for the next several days, my room will look like it does now: clothes strewn everywhere, torn shoes from 2011 stuffed in whatever cubby of empty space is left in my overflowing closet. I might put on and take off my light-wash jeans six more times before going to my friend’s improv show, even though I know that no one will comment on them. It’s an overcorrection, but for me, that’s growth — the sort of conscious, deliberate mistake I would’ve been way too proud to make a year ago.

I live in Portland and write for a magazine. Nice!

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