How I Dressed for Anonymity on a Road Trip to Maine - Pretend Vacation

How I Dressed for Anonymity on a Road Trip to Maine

Fashion-wise, one of my favorite moods to be in is “Please Do Not Perceive Me.” In the past, it has driven me to track down very specific secondhand zip-up hoodies and very loose overalls. It’s the look of the masc girl from a John Hughes movie who works in an auto shop and places comfort over all else. Her clothes are functional, boxy, and (most importantly) easy to skateboard in.

On the spectrum of loose clothing, the 90s unbothered look is at one end and divorceé linens are on the other. You know, the linens that flow in the ocean breeze as a woman of a certain age starts her life over again. You usually see them in movies marketed towards women who are of a certain age and have just started their lives over again.

I may not be much of a skateboarder (as in, I can’t even stand up on one- but that’s a discussion for later), and will sprint away from loose linen bag dresses with all of my strength, but I gravitate to a certain strain of the loose, unbothered clothing look. I like the anonymity of it. Especially as a Lady with a Lady Body, it is massively relaxing to wear something cut in a way that radically de-emphasizes any curvy bits. Sometimes, we are tired of being noticed. Sometimes we want to dress like we’re about to paint some houses.

The thing is that anonymity shifts depending on one’s environment. Because, as comfortingly masculine and casual as a big pair of overalls can be, they aren’t entirely nondescript. They are, generally, a Look. So, what to do when we just want to blend? When external perception is our enemy? I constructed a few anonymity recipes on a recent drive up to Maine, where I was camping alone (except for my dog) and wanted to draw as little attention to myself as possible. So-

Night 1 — Blending on Cape Cod

I was lucky enough to get to visit a sweet friend of mine on the way up to Maine and stayed with her family on Cape Cod overnight. Summery layers feel like an East Coast look for July, especially in a cute coastal town. I popped on my navy platform sneakers from Everlane- canvas, and in a shape that feels sailboat-friendly- some blue jeans, a tank top, and garnished the whole look with an oversized white button-down. 

The palette was a summery neutral, with the navy sneakers and white button-down adding a posh element that felt appropriate to the setting. It felt very one-of-Logan’s-friends-from-Gilmore-Girls. I wore the same look for Night 2 when I stayed at an inn near Bar Harbor.

Nights 3–6 — Blending in the Woods

Leading up to the camping piece of my trip, I was on alert for any sketchy energy since I was camping alone. Happily, the campground was fairly populated with entirely friendly people who were just as pleased as I was to be sleeping in nature for a few nights. 

Still, it was important to me that I appear nonchalant and Not Lost, i.e., I don’t need any help putting up my tent thank you. 

My go-to outfit in the woods involved hiking boots (see? I’m prepared! I have special boots!), hiking shorts with lots of pockets, and a cozy big fleece that brought the whole look to the lowest possible register of effort. I even used a carabiner to attach Elmer’s leash to my belt loop. Don’t be intimidated, you can say hi to us. Expert outdoorsmen are people too.

Night 7 — Blending in the CITY

Looping back down the coast, I was near giddy to be staying in Boston for a night before getting back to New York City. I stayed at a hotel where I got to shower and everything! It was glorious. Weirdly, being in the woods for a few days did wonders for my self-image. I started the trip feeling meh to neutral about the whole corporeal form thing, but I finished it feeling SEXY. I’m awaiting further analysis on what exactly made that happen, but it was a welcome shift. 

That said, I didn’t really have any outfits to express this, let alone to go out on the town in. Luckily, I was able to match a pair of black leggings and a black athletic top, and thus disguised myself as one of the many women on Newbury Street going to or coming from spin class. I even wore sunglasses and my HOKA sneakers. It was fun to costume myself into an image of the everyday, even if it doesn’t necessarily reflect Myself. Or maybe it does? Again, further analysis is needed.

Clothing is a bizarre personal project to take on. I’m definitely still navigating the gap between what I think I like and what I like to be physically on me. But filtering changing environments through my Self has been an educational way to play with my appearance and experiment with what is actually comfortable or exciting. Remember, you’re so cute! Go have fun!

- Helen



 

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