In ELLE.com’s monthly series Office Hours, we ask people in powerful positions to take us through their first jobs, worst jobs, and everything in between. This month, we spoke to self-proclaimed nap enthusiast Nell Diamond, founder and CEO of Hill House, and the brains behind the viral Nap Dress® (yes, she trademarked it). “It was aligned with my whole idea that I’m like a Victorian ghost who can nap anywhere—like, I need a fainting couch,” she tells ELLE.com of the brand’s unexpected hero piece. “I wanted a dress that, at any moment, I could take just lay down and take a nap in, because I’m that comfortable. I never thought the name would catch on like it did.” Diamond recalls the first time her brand sold out of its tartan Nap Dresses in December 2019. “We thought it was a mistake. We didn’t know what was happening. We were stressed, then we realized it was a good thing.” Ahead of Hill House’s pre-fall collection launch today, Diamond discusses everything from her first job at Abercrombie to giving up on the idea of perfection.
My first job
I worked at the first Abercrombie ever on Savile Row in England. At the time, I was so deeply, darkly obsessed with Abercrombie. For context, I grew up in the U.K., but with an American accent and American parents. This was in the era of movies like Bring It On and Americana—Abercrombie was this completely foreign, amazing thing to me. And nobody at that point did brand identity quite like them, with the perfume as you walked into the store. They recruited at my school, the American School in London, because they wanted people with American accents. It was very short-lived, because I was still in high school, but you could not have told me I didn’t win the Nobel Prize when they gave me that job offer—I took it very seriously. For me, working in retail is an absolute must. I literally will not allow my kids to not work in retail.
My worst job
I don’t want to name and shame them, because one of my biggest red flags in interviews is when people like, talk smack about their previous employer, but what I didn’t like about [the job] was there was very much a culture of quizzing people. There was an older person in my group who would try and stump me all the time, and I was so nervous that I would come into work sweating. The role was very math-focused, and it gave me anxiety at night to the point where I could barely come into work the next morning. There was very much a fail hard, fail fast mentality, which has never been my vibe.
How I foster a positive workplace culture
It’s all about having perspective. Getting accidentally pregnant in 2016 turned out to be one of the best things that ever happened to me. It happened six weeks after I launched Hill House, and I was raising my first son, Henry, at the same time as I was building a business. The same day I found out, my one employee quit, so for the first four months, I was doing it completely on my own. I thought, what have I gotten myself into? I’m usually such a planner. But I’m so glad it happened that way. I took myself a little too seriously before that. The experience forced me to be a lot more humble than I would have been otherwise. I realized that I couldn’t do everything at once, and what we are doing every day is not the most important thing in the world, especially in fashion.
Why I launched Hill House
I’ve always loved brands, and historically, I’ve had a real emotional attachment to the great brands of my youth: Topshop in its heyday in England was so formative to what I wore and how I thought about myself; I remember buying my first lipstick at MAC on King’s Road and it being such a huge moment for me. I’ve always expressed my identity through clothes and makeup and how I costume myself—it’s been a real creative outlet for me—but I never realized it could be a career. I went into finance right after college, and most of my internships were more analytical and quantitative; I had always envisioned using that side of my brain and the other, creative side just being for fun.
When I worked in finance, I was in a rotational program and spent some time watching a new generation of retail brands come up and exist, and I could not get the idea out of my head that I wanted to reimagine what a next-generation lifestyle brand would look like. So, I applied to business school with the very loose idea for Hill House, and while I was there, I interned for Louis Vuitton in its retail performance group, basically to convince myself to not start Hill House, because I think of myself as a very risk averse person. I thought, I don’t want to start a business; it’s so risky, it’s so scary; I love structure, it’s so unstructured; I love people, and I’ll be alone. But working at one of the most iconic brands in the world got me excited to figure it out for myself.
Why I started with bedding
I wanted to create what people wanted, and I didn’t want to put that in a box. I have a very specific passion for bedding, because I think that sleep and mental health are so closely linked, and waking up in a space that you really love can have such a meaningful effect on your psyche. And I feel the same way about clothing. Feeling like you look great—whatever that means to you—can have such a profound effect on how you go about your day. I straight up loved those old-school monograms on vintage printed linens and wanted to make them at a more accessible price in some really cool colors, so we started there. But I think from the very beginning, I wanted to figure out what products are going to make people feel happy and joyful and make their lives easier and make them feel great about themselves. With fashion, at first I thought I didn’t know enough—I never studied it, or I don’t have good enough taste, all those insecurities—but in the end, I’m so happy where we are, and I wouldn’t change a thing.
The origin of The Nap Dress
If I had gone into it thinking, this is going to be the hero product that’s going to change our brand, then I probably wouldn’t have named it The Nap Dress, because people might think it’s a nightgown. But in the moment, it was a name that was so personal to me and really made me giggle. It was aligned with my whole idea that I’m like a Victorian ghost who can nap anywhere—like, I need a fainting couch. I wanted a dress that, at any moment, I could take just lay down and take a nap in, because I’m that comfortable. I never thought the name would catch on like it did, but one thing that business school taught me is that regardless of whether you think something is going to resonate or not, if you come up with something, you trademark it. There’s this blind confidence that you have to have with everything you do as an entrepreneur that almost makes the hits indistinguishable from the misses. Every time we launch something, I’m proud to introduce it to the world, because it feels really special and has the opportunity to become something entirely different once people actually live in it. For example, the first round of Nap Dresses didn’t have pockets, and pockets very quickly became essential to the product and something people can’t live without.
My best advice for growing a business
Compare and despair. It can be so easy to start out, especially as an entrepreneur, and just compare yourself to all the other businesses that either started at the same time as you were in the same category as you. My best advice is that whenever somebody tells me they’re starting a business is to mentally hit mute. Your energy and your time is so precious; wasting energy on focusing on what other people are doing is not going to get you to the place where you deserve to be. It’s easier said than done; we all have our moments where we’re doomscrolling and just feeling that anxiety of comparison, but it’s so important. I think the mute feature on Instagram is the best thing ever for that feeling. If I feel a tinge of anxiety or comparison about a friend group or if somebody didn’t invite me to something, I hit mute.
On the importance of inclusivity
We created the design process from a place of genuine inclusion and truly wanting everybody to feel great, yet that’s not a talking point for us—it’s just something we do and we’ve always wanted to do and has continued to be really important to the depths of our product development. When that’s truly core to how you create the product, it then bleeds into how the customers react to it, and how the campaign is shot, and which models you use. I have friends who I want to wear this product; I want my 65-year-old mom to feel amazing in this product; I want my 15-year-old niece to feel great in the product…all of those things. I never got a great taste in my mouth from brands that make you feel like you have to like be a certain level of coolness to wear them. There’s a power in being uncool. I’ve been cringe since I was born.
My proudest career moment so far
Retaining our team. Everyone has been here since those dark first four months. To me, that’s the ultimate measure of success as a leader—being able to foster a team that builds with the business through all its different phases. It’s very humbling for me to have people come in and bring their own vision to it. Also, giving up the idea of perfection. Even with Instagram, there would be times where I would sit there, ready to post, but it would not feel like the most on-brand, amazingly captioned photo, and I would get stuck and then just not post anything. I’m proud of moving through that and no longer experiencing inertia and getting paralyzed by choice. I think we’ve done that in a way that’s very true to the brand, by evolving our identity and not getting bogged down by perfectionism.
What the future holds for Hill House
Retail has been working really well for us. We’re taking long-term leases in quite a few of the spaces that we first opened pop-ups in and are looking at new markets, too. I’m obsessed with Hill House’s location in Rockefeller Center. I’m a big theater girlie—I love that whole vibe. I’ll always be a tourist at heart. It’s also been an amazing opportunity for people to try on the product. I think whenever you have a viral product, people will just hate on it for no reason. I remember seeing a tweet where someone said something rude about The Nap Dress, and my genuine, earnest reaction was, I promise if I get that on your body, you’re going to feel good.
This interview has been edited and condensed.
Claire Stern is the Digital Director of ELLE.com. Previously, she was Deputy Editor of ELLE.com. Her interests include fashion, food, travel, music, Peloton, and The Hills—not necessarily in that order. She used to have a Harriet the Spy notebook and isn’t ashamed to admit it.