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Fashion / Fashion & Grooming

How to Dress Like Caroline Calloway This Halloween


The year 2019 has blessed us with an abundance of memes, sensational scammers, and viral celeb moments—all ripe for the picking this #SpookySzn. is here to help you win Hallowmeme with our complete guide to costumes for people who love the Internet.

Who is Caroline Calloway?

Caroline Calloway

Noam GalaiGetty Images

Where to begin in the twisty tale that is the Caroline Calloway saga? The 27-year-old is one of Instagram’s original influencers and has since become, in the words of The New York Times, “a fixture in the digital daily tours of some young, literary, edgy people, particularly women.” She’s also, some people allege, a world class con artist. In 2015, she sold a book for an advance of $375,000, which she never wrote. She’s also organized “creativity workshops” that turned out to be total messes. In September, her Instagram caption ghostwriter (and brief maid) Natalie Beach penned a juicy exposé for The Cut about their lapsed friendship.

You should wear this costume if…

You can’t keep away from Calloway’s infamous Instagram account.

How to get it:

Flower Crown



Paint Set

US Art Supply


Selfie Stick



Blue Plates

Williams Sonoma


This costume is pretty easy: It’s all about the flower crown. At one of Calloway’s events advertised as a “seminar,” her online followers were invited to meet their idol IRL at a Brooklyn loft. The cost was $156. Originally, Calloway guaranteed that all attendees would receive a flower crown to—bear with me—learn “the secret to flower crowns.” However, according to Buzzfeed, Calloway had other plans.

She decided to use the flower money to pay for professional photographers instead (after initially asking for volunteers to do free photography, she faced fans’ blowback and agreed that paying them was the right thing to do). Instead of giving everyone a flower crown as a favor, she clipped a few flowers into their hair as they posed for a photo, then reused them for the next guest. Andrea Park, who wrote about attending the event half-ironically on W Magazine’s website, said that when Calloway clipped the flower to Park’s hair, she whispered, “The secret to flower crowns is there is no secret.”

Pair your phony flower crown with a piece of art (Calloway is now making money as a visual artist), a selfie stick, and some blue plates.

Staff Writer
Rose is a Staff Writer at covering culture, news, and women’s issues.

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