Nell Diamond on Designing the Nap Dress

You might be forgiven, if you are one of the people who have seen a company called Hill House Home selling a nostalgic-looking smocked nightgown called “The Nap Dress,” in thinking this was another attempt to capitalize on a crisis. Perhaps it entered the peripheral vision of your targeted ads, alongside one of the many new brands that are trying to sell you on a need you wouldn’t have had before you realized you were living through a world-historic reshaping of every part of human life. Like sourdough starter and standing desks, the products of early quarantine have taken on an aura of historical archive: today in your living room, tomorrow an illustration on an educational infographic.

Yet the Nap Dress is not exactly new, and certainly not intended for a pandemic. The ways in which its success has been turned into a story says more about the people telling it than the item, the company that produced it, or the woman who is the face of both: Nell Diamond, the 32-year-old CEO and founder of Hill House Home, a direct-to-consumer line of bedding, bath, and apparel that launched in 2016.

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When I spoke with Diamond, it was February and she was Zooming from her West Village townhouse. She told me her home office has moved to different locations throughout the pandemic, all of which correspond to different phases of mood: there was a period, she shared, of working in the basement with no windows, the better to focus on the most intense work. On the days we talked she was in her bedroom window phase, and behind her shoulder there was a glimpse of a canopied bed and soft beige chaise lounge. This is the getting-some-sunlight stage, with views onto her neighbor’s comings and goings—an approximation for what counts as co-working during a time of necessary isolation. Her long, dark auburn hair was held back by the brand’s Halo headband, a pink moiré crown that curved behind her ears; she was wearing the Nesli Nap Dress in a light blue glitter check as well as a collection of necklaces and earrings.

Before we launched the Nap Dress, I remember getting really nervous… I was like, this could totally be what everybody calls a Nell thing.

“The prevailing message has been to paint any growth as a pandemic story,” said Diamond. “And certainly, our products work well when you’re at home. At the same time, we saw real, meaningful growth before the pandemic, and not one of our products was designed during it. Everything existed, and I would say had cult-level followings, before this year.”

Diamond wants to stress that Hill House Home, as a business, was built to withstand almost anything: she has deliberately kept a low overhead, scaling the business in a way that minimizes waste and risk. “Before we launched the Nap Dress, I remember getting really nervous,” Diamond recalled. “I was like, this could totally be what everybody calls a Nell thing, and I worried about that. But it became clear to us the day that we launched that this product was special.”

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What is a Nell thing? A cat eye is a Nell thing—liquid eyeliner worn everywhere from the earliest Zoom meetings to, as she detailed in a post for Into the Gloss, the birth of her twin babies (it never smudged). Heart-shaped sunglasses. High, high heels. Long, long, long hair, sometimes tied with a monogrammed grosgrain bow. Characteristics that are pointedly and archetypically feminine in their intentions. Diamond has kept a catalog of the moments when her Nell things were called into question, and told me stories she’s also shared in Instagram captions before: the middle school teacher who yelled at her for wearing glitter eye shadow, another teacher who berated her for being afraid to climb a mountain. “I’m really sad for the version of myself that felt I needed to prove why I wanted to present myself this way,” she reflected, “and the internalized misogyny.”

I’m really sad for the version of myself that felt I needed to prove why I wanted to present myself this way…and the internalized misogyny.

Another Nell thing is being really, really good at Instagram—as of this writing, she has over 56,100 followers. “She has such a strong voice, aesthetic, authenticity. If you look at her profile, you’re like, ok, I get what this brand means immediately,” said Eva Chen, the head of fashion partnerships at Instagram. “She innately lives and breathes Instagram.” On Diamond’s profile, a follower will see babies, beaches, the behind-the-scenes of a day in the life that the platform has become known for—the chosen visual expressions of a personality. Diamond is so convincing, Chen said, that her colleagues block out time on their work calendars to get the latest Nap Dress style when it drops.

The fashion designer Prabal Gurung considers Diamond, whom he’s known for a decade, as a cross between family and muse. “When I do a runway show, and I come to take my last bow, I always look for Nell’s face to see her beaming with pride,” Gurung said. He designed one of Diamond’s two wedding dresses (the other was designed by Olivier Theyskens) for her weekend-long celebration at the Hôtel du Cap-Eden-Roc on the French Riviera, a location that most often appears in reports about Cannes Film Festival parties and F. Scott Fitzgerald novels.

From L-R: The Ellie Nap Dress in blue botanical, the Nesli Nap Dress in black

COURTESY

Diamond was always, as she often says, “a dress girl.” Dresses are another Nell thing; an item of clothing that is prettiest to the kind of person who considers it practical. Diamond found out she was pregnant just a week after officially opening Hill House Home, and as somebody who considers herself highly structured and intensely organized, this was certainly above and beyond what anyone could expect while expecting. Diamond’s pregnancies have so far all coincided with moments of extreme change: along with her first child Henry being born in her first year of business, she found out she was pregnant with twins Willow and Sebastian, who were born in October, right before New York prepared to go into lockdown. (Her husband, Teddy Wasserman, works in private equity; he is the namesake of the Teddy Suit, a matching sweater and sweatpants.) “I wanted to design something that allowed me to feel like myself during a 3:00 am feeding, when I’m so bone-tired and have four thousand emails and I’m thinking about taxes and my laundry and my to-do list,” she recalled, “and the Nap Dress came to be as a solution to a problem inherent in my own life.”

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The product development was, in her words, “relentless”—an exacting process of making sure that it could be the highest possible quality at the lowest possible price point. The name, Diamond pointed out, is something of a misnomer; everyone I speak to who owns a Nap Dress quickly extols its virtues not for snoozing but as an above-the-waist look for on-camera work meetings. The price ranges between $75 and $150: still a substantial investment, but a not entirely unreasonable amount for the customer who really loves them, which is, as it turns out, a lot of people. In February 2021, the same month that a long-awaited black Nap Dress was released, Hill House Home sold $1 million worth of inventory in 12 minutes. Fifty percent of all Hill House Homes sales are Nap Dresses—not least because the typical Nap Dress customer owns, on average, three of them.

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Sleepwear in women’s fashion has often had the feeling of being commes des garçons—in borrowing from the boys, there is the vision of a pair of boxer shorts and a baggy t-shirt, or as preferred in romantic comedies, a man’s button-down shirt adorably large on a small, shapely frame. Pajamas first took on high fashion status when Coco Chanel, in the 1920s, stole the concept from a common kind of sleeping garment for Indian men—the word itself comes from the Hindi “payjama,” loosely translated into “leg covering,” and centuries of British colonialists had already stolen the nighttime matching shirt-and-trousers look and made it their own.

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From L-R: A still from The Virgin Suicides, Claudette Colbert in The Palm Beach Story

Alamy,Getty Images

Hill House Home and the Nap Dress, in particular, are not exactly following in that model of nighttime attire. Diamond’s aesthetic, rather, rests on a miscellany of references, some of which converge and most that contradict. The Nap Dress could be worn by both a less sanctimonious Jane Eyre and a better-understood Bertha Mason. It could be for Audrey Hepburn’s princess-in-disguise in Roman Holiday, or for a Lux Lisbon who meets a different fate than the ending of The Virgin Suicides. It could be the cherished centerpiece of a haunted doll’s wardrobe, or the sweetly wrinkled ensemble of a cherub who overslept. When Marie Antoinette began spending time at Versailles in the 1770s, she asked her dressmakers to create something light for reading Descartes in the grass—the Nap Dress could certainly be for a queen who wants to play milkmaid.

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Audrey Hepburn in Roman Holiday and Breakfast at Tiffanys

EverettGetty Images

As a fellow designer, Gurung recognized that Diamond’s Nap Dress is something rare. “She’s been able to breathe the zeitgeist and the culture into an inanimate object,” he explained, “which is the most difficult thing to do. This particular moment in history will be forever remembered for the emotions we felt, the social awakenings that we saw, the global reckonings—everything changed. I do think people will remember the Nap Dress with nostalgia, and with nostalgia comes conflict; this item is more than a comfort. It will be a memory of how, in a pandemic, there was hope. I think it will stand the test of time, and what I really love about it is that in a world with headlines like “Sweatpants Forever,” here was an option that it doesn’t always have to be. And what a beautiful option.”

Gurung is referring to Irina Aleksander’s essay for The New York Times Magazine, “Sweatpants Forever,” a profile of Scott Sternberg, the founder of Entireworld, a line of direct-to-consumer sweatsuits. Early in the pandemic, he wrote an honest newsletter to customers expressing his anxieties and uncertainties about what the pandemic would do to his business. On an average day before the pandemic, Aleksander reported, Entireworld—which, like Hill House Home, also offers well-priced and distinctly designed comfortable basics—sold 46 sweatpants in a day. The day of Sternberg’s email they sold 1,000 pairs. Within a month, sales across the brand were up 622 percent from the previous year.

“She’s been able to breathe the zeitgeist and the culture into an inanimate object,” he explained, “which is the most difficult thing to do.”

It would be too simple to say that this astounding economic growth was the result of being in the right place at the right time—yes, in a moment when some people are orbiting between different kinds of horizontal positions on various soft surfaces, it makes sense that loungewear and sleepwear would become favored outfits. But Diamond and Sternberg are more accurately understood as business owners who have seen the long history of ready-to-wear clothing and direct-to-consumer operations systemically devalued by weakening labor rights, unsustainable production schedules, and unforgivable environmental destruction, and decided not to repeat history’s mistakes.

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Diamond, a graduate of Princeton with an MBA from Yale, describes herself as an apt and active student. Gurung said he often teases her by asking if she was always the first kid in class to raise her hand, which she readily admits she was. In second grade, she told me, she received an award for perfect attendance and could not be convinced it wasn’t an honor on par with a Nobel Peace Prize.

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Allie Holloway

nell diamond

Allie Holloway

In those formative years, the Diamond family moved from the United States to Japan to England, rarely spending more than a few years in the same school. “I remember being very quick to figure out their codes,” she said. “It was really like a street map, figuring out the anthropology of a school so I could make my way. It wasn’t because I wanted to fit in—I knew that was a futile exercise. From a very early age, I was forced to figure out what felt good to me, what made me really happy, and then relentlessly pursue it. The alternative would be to change myself every couple of years, or be unhappy.”

I was forced to figure out what felt good to me, what made me really happy, and then relentlessly pursue it.

One of Diamond’s favorite works of literary criticism, she told me, is The Madwoman in the Attic, one of the definitive texts for rereading and rethinking the role first wives and other hysterics have played in romantic, gothic, and otherwise canonical tropes. Her Princeton thesis, “The Cultural Myth of Female Hair in the Victorian Imagination,” traced references to women’s hair from the Old Testament to the New, from Greek mythology to Disney movies, from the pre-Raphaelites to flappers. I wondered if Diamond has any personal aspirations to be a writer herself, and she replied that she’s never met an English major who didn’t aspire to be a writer. “I would say that personal, kind of confessional writing on Instagram has helped me get through really intense moments in my life in the past five to ten years, and I think especially around motherhood it’s been such an amazing outlet.” She briefly showed me her nightstand, which could be an immaculately curated table at the front of an independent bookstore: it is piled high with recently released novels by Brandon Taylor, Brit Bennett, Bryan Washington, Raven Leilani, and Torrey Peters, among many others.

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In June of last year, as protests against police brutality and institutionalized anti-Black racism spread across America and throughout the entire world, a slew of overdue reckonings came for people loosely in Diamond’s same cohort—millennial women who sold ideas, products, or services under the guise of feminism, and whose workers collectively came forward in the past year to share stories of the way they ran exploitative, oppressive workplaces. When asked if she’d paid attention to it, Diamond relayed the following story: “Early in my career, my parents told me to keep my blinders on as much as possible, and put my head down and do my own work. It relates to doing your homework when you’re young, and it relates to your work later—when you’re looking over your desk to the next table, I think it really pushes you off your direction.”

I really try to stay in my own lane and think about what we’re doing.

Diamond’s parents are an influential presence for her: she speaks about her close relationship with her mother, and has often shared stories on Instagram about how much she admires her mother’s grace and fortitude in raising three children far away from her own home, and more recently, overcoming breast cancer. Her father is a banking executive, who resigned as the president and chief executive at Barclay’s bank in 2012 as a result of a lending rates scandal. At the time, the then-23-year-old Diamond tweeted and then quickly deleted that UK politicians George Osborne and Ed Miliband, who called on her father to step down, could “go ahead and #HMD,” the hash-tagged acronym for “hold my dick” presumably for brevity as well as effect. As Bim Adewunmi wrote in an op-ed for The Guardian, this was a moment in which Diamond failed to read the room. Now, in thinking about her own company, she said, “I really try to stay in my own lane and think about what we’re doing.”

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Diamond brought on Dr. Akilah Cadet, an anti-racism consultant and advisor, in June of 2020 to create their Diversity and Inclusion Board. Dr. Cadet consults on everyday business needs, such as hiring practices, as well as managing and advising the disbursement of the brand’s $100,000 pledge to different organizations focused on racial justice and equity.

I spoke with Dr. Cadet from her home in Oakland, where she was wearing her own Nap Dress (though not the one named after herself, which was launched on the site shortly after she was brought on). Her business, Change Cadet, offers organizational development consulting for active, measurable strategies to ensure diverse, equitable workplaces. Dr. Cadet told me that she hopes other brands and businesses learn from Diamond specifically: she believes that would result in more brands that are truly inclusive, inside and out. “Nell is the epitome of what a leader should be for a company, but primarily for a white person with privilege and a white woman who is a leader,” she said. “What I help a lot of companies do is realize that their power is actually in role-modeling the behavior of learning and unlearning: not knowing, figuring it out, partnering with people in your team and companies like mine. And Nell does that with absolutely no problem. She looks at her systems and her structures as a true ally, making sure that they don’t uphold values of white supremacy.”

You can’t think about building an anti-racist company, or building a company that’s doing thoughtful things for the world if you don’t think about how your supply chain affects people at each stage.

When Diamond describes what she means when she calls herself a feminist, she speaks immediately of race and class. As a student of literature and art history, she is quick to point out that her perspective has been warped by a white Western canon; as the founder of a rapidly growing company, she talks about how anti-racism is a foundational principle of all their business decisions. This applies to casting the models on the site and in the Instagram posts, but more importantly, it also means that Hill House Home reports a fair process for every worker in their company—transparent hiring practices, clear paths to promotion, and good compensation. Last June, Diamond posted a breakdown of the current demographics for all paid influencers and employees and instituted a yearly public review to ensure that they remain accountable to their stated goals of parity and representation in all levels of the company.

Along the supply chain, as well, there are extensive vetting requirements from independent experts to ensure that their production is equally safe. (One of those experts, a consultant for the Angora Group that provides research and sourcing for fashion production, is the namesake of the Nesli Nap Dress.) “You can’t think about building an anti-racist company, or building a company that’s doing thoughtful things for the world if you don’t think about how your supply chain affects people at each stage,” Diamond said.

“I feel a tremendous amount of responsibility towards the people that I work with,” Diamond added, admitting that she often feels nervous about how difficult it is to speak clearly in conversations about power and capital. “When I say that I’m the CEO, I mean I’m actually doing the work of a CEO in a business; I don’t want to be the empty face of a brand. I don’t take any of this lightly. My team deserves honesty and respect.”

I promise, if you put this on, you will like it.

For many years, the model of the impressively young CEO was of a man who ran his tech monopoly as a force to destabilize democracy while wearing the clothes of a middle schooler allowed to pick his own outfit for the first day back at school. It was hardly a success when the girlbosses, as the cohort of pretty white brunettes who made themselves into the faces of their products came to be known, defined success as the same brutal abuses of power, only this time with blowouts and Cartier bracelets.

When I asked if there are any companies that Diamond believes represent an ethical way of doing business, she cites Yvon Chouinard from Patagonia and Ben & Jerry’s as role models, though she also wants to be clear that no business, under capitalism, can be perfect—rather, she believes that ethical business practices are not diametrically opposed to having a profitable company. “We believe that these products provide value in your life,” she explained, “but we’re not trying to hide behind any flowery language: if someone is handing over their hard-earned dollars I want to make this product the absolute best I can make it for them. This is an English teacher thing, too,” Diamond said, “but I am like: show, don’t tell. I want to prove this concept—to show the people who are wearing Nap Dresses every day on their Zooms, or to sleep on their sheets, and they’re happy.”

Diamond’s dreams for the near future are small. “I want to bring my babies outside,” she said—to introduce her children to her friends, to stroll on the West Side Highway. She is still thinking about how to continue to grow her business without sacrificing the principles that have made it stand strong so far; a line of Nap Dresses for “littles” launched mid-April, and bridal will follow in May. Diamond has, like her name, a bright, hard certainty: what she’s doing might not be for you, and that’s ok, but she will take any chance she gets to prove you wrong. “I’ve seen people get a little snarky about the Nap Dress,” Diamond admitted, “and the only thing I want to ask is: what’s your address? It’s like, I promise, if you put this on, you will like it.”

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Photographs by Allie Holloway; Stylist Carrie Goldberg; Hair by Clay Nielsen; Makeup by Dana Rae; Production by Ignacio Murillo.