The Upper West Side’s ‘Masked Hatter’ Makes Fashion Statements, and Public Health Ones Too

By Amelia Roth-Dishy

With nearly nine months of mask-wearing under our belts, most of us have experimented with the style, fabric, or pattern of this newly mandatory face accessory in some way.

But one Upper West Sider has turned the art of masking up into just that: a genuinely artistic enterprise.

Elizabeth Sobieski, who goes by @themaskedhatter on Instagram, began posting selfies of herself wearing assorted masks back in early May. She coordinates each unique mask with a fabulous hat and a pair of sunglasses. Effusive captions detailing the mask and other garments being modeled accompany each image. To date, she has shared 140 looks on her page, all taken by hand— the account has a self-imposed “no selfie sticks allowed” rule. The Rag caught up with Sobieski to discuss the project and its origins.

“When the pandemic began, I started to find myself all alone and isolated and I started to entertain myself by shooting these selfies,” she said. “It’s kind of grown and grown into a big project.”

Sobieski, an arts writer and novelist, has an extensive vintage hat collection that includes pieces from designers such as Phil Tracy, Eric Javits, and Marie Marcié. She also had a drawer full of sunglasses on hand, but once she began the account in earnest, she noted, “I admit I began to acquire more.” Flying Tiger was a favored spot for cheap, fanciful glasses until it closed last month. 

And in terms of the all-important masks? “I’ve gotten them from all over the place,” she said. “I get a lot from Etsy, and I’ve got some from New York designers like Dizzy Lizzy, Michael Kay, and Batsheva Hay, who’s an Upper West Sider. And I just put them together in various combinations.”

She purchased her first face coverings in January. “Even though our government didn’t understand that we were going to need them, for some reason or another, I knew we were going to need them,” she said. But they were more or less gas masks and generated some strange looks when she would go shopping at Barzini’s. Since then, her masked stylings, and unexpected accessory pairings, have flourished, catching the attention of admirers both on and offline.

“Usually people say very nice things, like oh, what a great look, or that’s cool,” she added. The Masked Hatter has only gotten one negative reaction on the street, in Riverside Park: “This man walks by me and says ‘rat lady.’ I was wearing a nice hat and a nice mask with a pattern on it that was not a rat,” she chuckled, “but maybe he was just a mad rat himself.”

The masks run the gamut from cheetah prints to sequins, Groucho Marx moustaches to textured blue feathers and more sculptural pieces.

 

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A post shared by Elizabeth Sobieski (@themaskedhatter)

She’s currently awaiting a mask from St. Petersburg that allegedly glows with black light.

One of her favorites, though she struggles to isolate just one, is a simple number with an important message: “DR Fauci said so.”

 

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A post shared by Elizabeth Sobieski (@themaskedhatter)

“It’s written in bold letters,” she said. “And people will ask ‘what did he say?’ Wear a mask.” Sobieski is pleased with the masking diligence on the Upper West Side, which has increased since the start of the pandemic, but she has her concerns. “Little kids are great and keep their masks on really well, and adults are terrific,” she said, “but teenagers I find are problematic mask-wearers.” She takes care to actively promote masks as public health guidance on her account, imploring her readers to follow her lead.

But the Masked Hatter is more than just a clever PSA or an Instagram handle— it’s a persona, a fashionable and mysterious pandemic-era figure with a truly killer hat collection on standby.

“It’s basically this character I’ve created, this kind of secret identity,” Sobieski said, adding with a laugh, “I think I read too many comic books when I was growing up.

“But it gave me a certain freedom, with this invisibility— because you couldn’t see my face, it was just a hat, a mask, and sunglasses— I felt very comfortable walking around taking these selfies.”

You may have seen Sobieski traversing the Upper West Side in her glamorous looks over the past few months. Of the roughly 140 selfies on her account, all but one were taken in the neighborhood, between Lincoln Center and Straus Park on 107th Street. (The outlier is in a swimming pool, from a two-day trip out of the city in July— the caption reads, “For the first time in 4 and a half months, the Masked Hatter has emerged from the Upper West Side.”)  Sobieski often dispatches from local landmarks and gives some corresponding history in the caption. Among her many photos, she’s posed in front of Zabars, Harry’s Shoes, the Shade Store, Riverside Park tennis courts, and the Dakota; and with (the statues of) Frederick Douglass, Abraham Lincoln, and Elizabeth Cady Stanton.

“It’s very much about the Upper West Side,” Sobieski said, “and very much about these COVID-19 times in which we live.”

Indeed, the conceptual, time-capsule potential of The Masked Hatter has not gone unnoticed. The account was recently featured in a digital gallery show at the University of Massachusetts, in a gallery in Denver, and in the International Center of Photography on Essex Street.

“What I’m hoping to do eventually is to turn it into a little book,” Sobieski said. “ I do describe what’s going on, like last week I had one up where I’m under one of the outside restaurant structures on Amsterdam Avenue. I think it would be an interesting gift book and also a kind of a memory of this very strange time we’re living in.”