I Lived Like Instagram Trainwreck Caroline Calloway for a Week

A week in the life of the infamous Instagram blogger and former NYU student is full of spin classes, leggings and oversharing.

Caroline Calloway has become an internet sensation over the past few years, known for documenting her life on Instagram. (Via Wikimedia)

Caroline Calloway is a lot of things. Instagram personality. Former NYU student. Prone to oversharing. Self-proclaimed “manic pixie nightmare.” With over 700,000 Instagram followers, multiple profiles in reputable publications and a loyal band of Reddit trolls, it might not be too far of a reach to call her a social media celebrity.

After reading about her in her former friend and ghostwriter Natalie Beach’s much anticipated expose in The Cut this summer, I went down a Calloway-shaped rabbit hole. I became obsessed with how her life could be so chaotic yet simultaneously charmed. Her Instagram is a trainwreck you can’t seem to look away from, with captions the length of short stories. Her West Village apartment is littered with burning candles on a rug that looks like it could go up in flames at any moment.

She is so self-obsessed that it’s almost endearing. Calloway is unhinged and deluded and yet I would still trade my own life for hers. And so, I did what any New Yorker with access to spin class would do: I emulated Calloway for a week.

I’m already a spin class regular, so that part was easy to nail. Sadly, I don’t have easy access to pilates or therapy, but I was sure to post every spin class on my Instagram story, as one Calloway always does.

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As this happened to be Thanksgiving week, I went home for the holidays (which, coincidentally, Calloway posted about a lot this week). My airport look was premeditated to emulate Calloway’s athleisure vibe. I decided to go with an Outdoor Voices workout set and a Pretties baby tee only because I was fairly certain she had worn that exact outfit to the airport on her way home from a vacation in Florida this summer. And, if not, she had definitely worn the combo to some sort of spin/pilates/therapy/sauna outing.

It should be noted that I am strictly a no leggings girl unless I’m working out. If Gossip Girl taught me anything, it’s that tights are not pants, so this was probably the hardest part of my experiment. That being said, I did notice a lot of people stopping to look at me (hopefully not for the wrong reasons), so maybe Calloway is onto something.

Besides daily spin posts and outfit pictures that I deemed worthy of my story, I was sure to include some thought-provoking and quirky posts. If Calloway has taught me anything it’s that personal brand is of the utmost importance, so I did tweak a few of my normal posts to fit the Calloway-esque agenda. My faux-deep posts ranged from art to social issues. On the other hand, my funny content mainly consisted of cringe-worthy text messages that I felt people would appreciate on some level.

But here’s the thing. To truly live like Calloway, you need to let go of all inhibitions and disregard reality. You post what you want to post because you think your opinion is important. You overshare because you think that using your regular Instagram as a diary is some new wave of quirky feminism that the rest of us plebeians have yet to achieve. And perhaps my favorite Calloway trademark of all: you create elementary school level watercolor paintings with boobs drawn on them and sell them from $120-$320 because yes, you believe your art is that important. To live like Calloway is to simply lose all sense of reality, and have a great time doing so.

Unfortunately, I was not graced with the confidence nor comfortable financial situation of my favorite Instagram trainwreck, but living sort of like her for one week was one of the most freeing experiences of my life thus far. Please never stop posting, Caroline. Your stories make me feel like I have my life together — even when I so obviously don’t — and what could be more rewarding than that?

A version of this article appears in the Monday, Dec. 2, 2019, print edition. Email Daniela Ortiz at [email protected] 

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