A Week in the Life of a Boarding School Student: OOTD

Boarding school life has taught me a lot about myself and the world around me. Being an only child, I’ve always valued the privacy of my bedroom, my place of comfort. But I’m not someone who likes to stay comfortable for too long; I live for adventure and embrace change. That’s why I chose to attend school all the way across the country in Connecticut: I wanted to try something new.

After spending four years at boarding school, I often forget how unique my experience living on campus for high school really is. In my home state, California, there’s often the misconception that boarding school is just another name for rehab, and I’ve frequently been asked what I did to get in (my freshmen year, a few well-meaning friends from home accidentally started a trending hashtag of FreeSkylar when they thought I was being shipped to a juvenile prison). Despite my initial nervousness to learn how to share my space, dorm life quickly became my favorite part of boarding school. Being able to live with people from all over the world— quite literally, as I’ve had roommates from Kenya, Saudi Arabia, and Hong Kong— is incredible.


Today was an extremely busy day— I had a quest in biology on photosynthesis processes and a quiz in Calculus. I felt really good about both assessments as I had prepared heavily during the past few days. On days that I have tests or quizzes, I always like to dress up a little extra because I believe when you dress well, you perform well. My life motto is “look good, feel good, do good.” There’s definitely some truth to that statement: when you look good, you feel confident, and therefore do better! Plus, there is no better feeling than getting compliments on your outfit.

Despite the business of the day, I had a relaxing evening. I’m the president of the Relive Your Childhood Club, which is an unofficial club dedicated to watching childhood movies. Tonight we watched Mulan, which is obviously one of the best movies of all time. Our meeting ended around 9:15 PM, which is fifteen minutes before weekday curfew. I spent the rest of the night studying for my Spanish quiz and FaceTimed a friend from home.


Today was a pretty chill day. My only assessment was in Spanish, and I felt pretty confident about the quiz (which was more like a handwritten in-class essay). After school I went to the gym with my friend. I’ve been hitting the gym way more often lately and it’s made a huge difference in my life. I’ve included a picture of my gym fit for today; I’m a fan of leggings and sports bras. Deliberately choosing fun gym outfits has really helped me gain confidence in all aspects of my workout routine: lifting in the weight room, running on the treadmill, doing ab circuits in the indoor track.

I went out to dinner with my friend at our favorite restaurant, Tavern on Main. We got sliders to celebrate her acceptance into college, which was really exciting. It’s kind of crazy to think that my friends and I will be leaving school so soon! Afterwards we exchanged our belated Christmas gifts for each other. As all you readers know by now, I am obsessed with Botticelli (just look at my header!) so her gift was especially perfect: a huge Birth of Venus tapestry. I rearranged my wall decorations so that it hangs right above my bed.

My bed’s made? Wow!


I had to wake up early today to give a tour of the school at 9:30 AM. As a part of Gold Key Society, the leadership organization in charge of giving tours of Choate, I am expected to promote my school by giving an amazing tour. When I first started touring, I could barely speak. I think it took me two months of constant practice and memorization to feel wholly comfortable giving tours— what I didn’t expect was to fall in love with them! Now I’m a Gold Key Leader, which means I teach other tour guides how to properly sell the school. I find this work really rewarding; it’s fun to mentor people who find this job just as exciting as I do.

After a late brunch at The Luncheonette, my friends and I went to Starbucks to grind out some work. Later, I went out to dinner at a local Italian restaurant with a different group of friends before seeing Little Women. It was such an entertaining and empowering movie! I loved it. We capped off the night with a fro-yo run.


Today was unusually warm: I spent most of the day in a T-shirt and sweatpants (which unfortunately I don’t have any great OOTD photos of). It was a pretty typical Sunday: I slept in, did homework for most of the day with a friend, and went out to a Mexican restaurant for dinner. During study hours, I gave two dorm presentations about sustainability initiatives on campus. As a Conservation Proctor, I often have to give dorm presentations to educate the student body on ways we can be more sustainable, whether it be reducing energy or knowing how to properly recycle.


Ah, Monday! I love this outfit because the purple of my jeans matches the purple lining of the heart on my sweater perfectly. It’s interesting how such a small detail can boost one’s confidence (and it certainly pays off– people notice the little details!)

Today was pretty mellow. I had a late basketball practice from 7-8:30 PM, which was intense. As a manager of Boys Varsity Basketball, I’m expected to set up the court and keep track of the clock. After practice I met with my math teacher to review the materials for my upcoming test. The rest of the night was spent studying in the common room with my fellow prefects.


Started off the day with a dining hall class where we discussed the decolonization of South America in Spanish over omelettes and iced coffee. While I’ve struggled with speaking Spanish in the past, this year I’ve found it’s easier for me to speak in another language when we’re discussing topics I’m passionate about. The rest of the day was quite busy: I had an art history paper due, a biology quiz, and a math test. I rewarded myself with a nap and SNL binge session after school.

For dinner I went up to our second campus, the Kohler Environmental Center. The food at the KEC is delicious, and it was nice to take a mini break off campus. Starting at 8:00, I began duty in the dorm. This year, I’m a prefect (similar to a residential adviser, we’re like the “older sisters” of the dorm) in the largest freshmen girls dorm. I’m on duty biweekly, checking in with every girl on two of the four floors, listening to their struggles and helping with homework. When I’m on duty, I bring candy to each room and ask to hear each girl’s “rose” (a highlight), “bud” (something they’re looking forward to), and “thorn” (a low). I adapt to each room accordingly, reading the room to see how engaged each girl is feeling on a particular day. I’ve learned how to support prefectees struggling with mental health issues, suicidal thoughts, family problems, and academic concerns. These moments can be hard and uncomfortable, but I’m so grateful I can be there for my prefectees, who trust and confide in me. 


Pretty simple outfit today. My favorite part of this outfit is definitely my hair tie; the ribbon feels so sophisticated!


Again, I’m back with the matchy-matchy! This time I went for a strong e-girl vibe, and I feel like the purple definitely added to my edginess. I’m a huge fan of the shirt over turtleneck look, and this striped turtleneck is perfect for layering with oversized shirts.

Bonus: Friday and Saturday!

This cardigan is extremely special to me because 1) it’s a gift from my mom and 2) I am a strong believer of manifestation. This cardigan reminds me of the power I have to connect with the Universe and manifest the life I want to have. Today I paired the cardigan with a white bodysuit and leggings; but don’t be fooled, it was freezing!

For my final look, I decided to go RED. I was inspired by my new shoes that had arrived the day before: a Fiorucci x Adidas collaboration. For color coordination, I always try to choose three pieces that match from the top to the bottom. For example, in this outfit, I match my jacket/sweater with my nails and the soles of my shoes. So when you look at the overall outfit, your eye travels from the top of my outfit to the bottom. As I’ve mentioned before, color coordination is really important because most people acknowledge it subconsciously.

On that note…

Thanks for joining me this week as I explored my experiences at boarding school! I hope you enjoyed reading this as much as I documenting my outfits and life. I’m also going to attach some random outfit photos I’ve taken in the past year so you can get a sense of Choate style over the seasons. But for now, I’m heading out, so I’ll see you at the next post! ❤️


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