020 - Outfit Repeater in Portland, Maine
May 13, 2025
I recently went on a solo trip to Portland, Maine for four days and three nights. Well technically I was in Portland for 2 nights and my grandpas house in New York for 1 night. I had just moved out of my Brooklyn apartment and was staying at Maggie’s house in Rockaway while she was out of town until my flight in early May. I had signed up for a NYRR race to qualify for the 2026 NYC Marathon, so I needed to stay in town for that before moving back to LA for the summer. (Yes, I will be running 2025 & 2026 NYC Marathon XD)
Maggie had driven her car from LA to NYC, and I was graced with the keys while she was away traveling. However, her friends were supposed to borrow the car over the weekend for a climbing trip. Lucky for me, it was raining and they canceled their plans, because, well, there’s not much rock climbing you can do in the rain. I found out late Friday night that they weren’t going, and I was happy knowing I’d have the car, mostly just to get around the city. I wasn’t even thinking I’d go on a road trip.
But I woke up Saturday morning and the first thought that hit me was: I have a car. I should go to Portland, Maine. It was one of those epiphany moments when your brain clearly worked something out while you were asleep. The best time that ever happened to me was in Brussels during the summer of 2021: I woke up and realized I finally understood exchange rates. (This makes me laugh, but it’s honestly true. It’s wonderful what a good nights sleep can do for you.)
As I always do naturally, I woke up quite early on Saturday, had the thought, and jumped out of bed to finish packing. I needed to finesse all of my bags before flying to LA. Basically, I was checking three bags to LA and needed to make sure they were all under 50 pounds. Whatever didn’t fit was staying with my grandpa. This took the better part of my morning, and honestly, the hardest part was packing for Portland. I didn’t want to take clothes out of my suitcases because I needed to know what I was checking vs. what I was leaving. I had a pile of folded laundry on Maggie’s desk and decided anything I packed to Maine would come from that pile.
I pulled a pair of pajamas: my velvet pants and my NY Liberty t-shirt. I grabbed my favorite pair of comfortable jeans—@COS denim. I grabbed my pink @Salomon shoes aka my self proclaimed travel shoes. I packed some (too much) workout clothes in case I wanted to go for a run and explore the town (which I never did). I added a white long-sleeve shirt, a grey t-shirt, my leather jacket, and my Carhartt rain jacket. To me, a perfect collection of clothes.
Historically, I’ve done a horrible job packing for short trips. I always bring the most ridiculous outfits thinking, Oh, I’ll wear something of my friend’s, or, I’ll wear my high school shorts that fit a 9-year-old, or, I’ll buy something. But this time, I thought: What outfit will make me happy and comfortable? I was feeling bittersweet about leaving New York and living in Rockaway, so I knew I was going to need little pick-me-ups to lift my spirits on this spontaneous vacation. I figured my cutest, most comfortable jeans, a classic white long sleeve, and a classic grey t-shirt would do the trick — honestly nothing feels more like me than this.
On the drive to Portland—which ended up taking me 7 hours because getting out of NYC took 2 (traffic + a wrong turn)—I wore my blue jeans and grey t-shirt. It was that spring/summer humid warmth in NYC, so I couldn’t wear more than a t-shirt. By the time I hit the Connecticut-Massachusetts border, it started to summer rain.
I got to Portland around 8 p.m. and asked the hostel worker where to go for dinner. He told me about a local bar across the street where I went, met a hammered group of locals, had a burger, some interesting conversations, and then I quickly left to go to sleep.
The next morning, it was much colder in Portland than NYC. It had dropped 20 degrees, so I definitely needed my long-sleeve shirt. I hadn’t even thought about this when I left, but I layered it under my short-sleeve t-shirt and served the best effortlessly cool girl outfit.
I got amazing baked goods, took the ferry to a nearby island, had a lobster roll, went secondhand shopping, and had the most amazing haul: Japanese denim jeans, a Rudy Jude top, and a Reformation shirt.
Here’s a lil dance of me in the lovely jeans.
I got back to the hostel around 5 p.m. and ran into my hostel friend. She was getting ready to go out to a concert and heal from a recent breakup. She was getting dressed and mentioned she didn’t feel like herself in her outfit—which is always the struggle when traveling. I completely agreed… except not really on this trip. I started to create an emotional attachment to my outfit. Granted, it was only my second day wearing it— I knew there would be a third, because I had severely underpacked and had nothing else. I did have my new secondhand clothes, but I weirdly compartmentalize clothes in my brain and I hadn’t washed them yet. I’m not sure if that makes sense to anyone else, but that’s just how it goes for me.
I went to dinner and had the most amazing gochujang bouillabaisse. It was kind of like Eric Kim’s gochujang stew, but with mussels and cod. It was incredible—I will definitely be making it at home. After that, I went back to the hostel, watched a movie, and went to sleep.
The next morning (Monday), similar to Friday, I woke up and immediately thought: I want to cut the drive back to NYC in half—so I’m going to Newport, Rhode Island. Dream location. I needed to see the Gilded Age “cottages” aka mansions. I got up at 8 a.m., put on my now-iconic outfit—Salomon sneakers, COS jeans, white long sleeve, grey t-shirt, Carhartt coat—hopped in the car, and drove three hours south to Newport. I visited the Vanderbilt mansion and walked the cliff trail. It started pouring and my jeans got soaked. I made it back to the car, changed my pants and shoes, got lobster pasta for dinner, and drove the rest of the way to my grandpa’s.
The next morning, I drove back to New York City—you guessed it—in my white long sleeve and grey t-shirt combo, but this time with grey leggings and green REI camping slippers. Going on my fourth day in this outfit, I never wanted to take it off. Unfortunately, I’m a stinky queen, and after four days of wearing the same thing, the pits started to reek of BO. I guess this was my sign: it was time to go home and change outfits.