Succeeding As A Fashion Designer Is Nearly Impossible. Here's How Tanya Taylor Did It.

It began at Starbucks. The always-busy one at Spring and Mercer in Manhattan’s SoHo neighborhood, a half-block north of the back entrance to Bloomingdale’s.

Tanya Taylor was looking over her vanilla latte at Will McLeod, the one person whom she could hire to start her eponymous clothing line with investment she describes as “really small” from “just friends and family.” She had just quit her job as assistant designer at Mary-Kate and Ashley Olsen’s clothing line Elizabeth and James. Failure was likely, this being a clothing line. But Taylor, who is Canadian, quickly realized she had to succeed simply in order to stay in New York on a visa. She said she is “not a good planner,” but at no point during our conversations do I believe her, and neither did McLeod, who took the job “because it seemed like she had her shit together.”

“I just didn't give myself the option it couldn't work, and worked my ass off to make sure it did,” said Taylor, 35, whose 10-year-old line is headquartered in an airy, Pinterest-perfect office on 18th Street with sweeping views of downtown Manhattan. The entryway’s mid-century modern armchairs in a warm shade of millennial pink give way to a cornflower blue cart, used recently for the “flower pop-up” Taylor held in Washington Square Park after her September New York Fashion Week show, which involved handing out bouquets affixed with a code people could scan to see the collection.

Taylor’s clothes are like a bouquet, and not just because that’s what they resemble. They’re both special and accessible, not an everyday thing but a treat. Tanya Taylor dresses are the ones you’ll lease from Rent the Runway or splurge on for your sister’s bridal shower at a price point industry types call “contemporary,” ranging from around $350 to $550. There’s nothing severe about her flowy cuts or floral prints, many hand-painted by Taylor herself. If Rick Owens were at one end of a spectrum of edginess, Taylor would be at the opposite.

But it’s a vision that’s landed her clothes in more than 100 stores across the United States and speaks to a range of women from sizes 0 to 22, 20-something to 60-something, and who live everywhere from Oregon to Tennessee. Michelle Obama, Beyoncé, and Lady Gaga have all worn Tanya Taylor. She is the type of woman entrepreneur who in 2017 might have been condescendingly labeled a “girlboss,” but who has methodically done everything she had to do, however uncomfortable (cold calls) to pragmatically build a business in an industry synonymous with flights of fancy.

And now she occupies a certain coveted place in that industry. “Tanya Taylor” is a regular name on the New York Fashion Week calendar, and Tanya Taylor the person is expected in the city’s social scene. Just last week, she threw a book party in her apartment for her close friend, famous Hillary Clinton aide Huma Abedin. Attendees included Natalie Massenet, the founder of Net-A-Porter, and Sarah Hoover, an art dealer from Gagosian. The pictures, which appeared in Vogue and were splashed across Instagram, practically sound like high heels clacking through her cavernous, art-saturated living space. It's the kind of stuff you'd expect on the average pandemic-free weeknight of a New York fashion type.

Before the pandemic, business was good. Taylor doubled her staff to 28, and 2019 sales were up 120% year-over-year to $10 million. But then the pandemic hit, women stopped buying floral dresses, and she lost 60% of her business.

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Taylor has a distinct memory of when she was 8 years old. She was having dinner with her mom and grandfather when they asked her, “Why haven’t you started a company yet?”

“And I'm like, ‘What?’ And they're like, ‘Start a bracelet company. Start selling to your friends at school,’” said Taylor. It’s not like she was the sales-y type. “Reclusive” and “very, very quiet” is how she described herself. She was nervous to make friends with anyone but the four girls she considered close. Her mom and grandfather ran their own oil and gas company, Shawcor, which invented pipeline coatings for intensely hot and cold temperatures and did $1.2 billion in revenue over the last 12 months. Her mom’s sister founded the company that became Corus, a kid’s TV station in Canada. Entrepreneurship was in her DNA. “I would get entrepreneurial kits for Christmas that were how-tos of understanding your customer and cost of goods,” Taylor said. Besides that, she enjoyed painting, mainly Grease-inspired pin-ups on the walls of her mom’s basement in the Toronto suburbs. (Her parents divorced when she was 4, and she spent weekends with her dad, a professor, who lived on a farm with goats.)

Her first job, at age 16, was “window display girl” at a vintage store in Toronto called Paper Bag Princess. After people with glamorous wardrobes died, their clothes ended up in the shop, and Taylor would use them to “create stories in the window.”

“It was a summer job, unpaid, and I begged for it. I thought I was just killing it,” she said. She worked there for three summers, earning a promotion to alterations, which involved hand-stitching clothes, a skill she learned from her mom and grandmother.

She later attended McGill University in Montreal, where she majored in finance instead of anything to do with art. “I love math. I love accounting. I, like, love calculus,” she said. But she quickly decided a career in finance wasn’t for her. Nor was taking over the family business. “I saw my mom do that, and I know she always kind of wishes she had done something more creative,” she said.

While a student at McGill, Taylor took a summer fashion course at London’s prestigious Central St. Martins art school. Her first day, a teacher told her and her classmates to put on white paint suits and “express yourself with color.” Taylor loved it, and shortly after abandoned her preparation for the LSAT and applied to Parsons School of Design instead. She got in and soon landed an internship working for the Olsens on their nascent Elizabeth and James contemporary line.

At just 22 years old, she was about the same age as her famous bosses, and because of her finance background, she was tasked with everything from managing budgets for the design team to sketching and sourcing fabrics. The internship turned into a full-time job that she held for two-and-a-half years.

“They loved this tone of oxblood,” Taylor said of the twins, whom she describes as “very different” from one another. “When it came fall time, there would be a million swatches of Bordeaux and reds and burgundies, and Mary-Kate would always go to the exact same tone and be like, ‘This is rich, this is my favorite.’” The pair lived between New York and Los Angeles and collected vintage fashion, including printed silk John Galliano robes, which they brought to the office where they’d “play dress up.” She added, "They were identifying what was missing in fashion through a lens of socializing and being that age."

But Taylor noticed something else while she was working for the Olsens: “There wasn't a lot of competition for feminine [clothing].” Nor did she see any brands that incorporated an art sensibility at the contemporary price point — everything that did was much more expensive.

So she decided to quit her job and do it herself. She said, “I just had this itch one day without a lot of planning and thought that it was the right time to be gutsy.”

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In the spring of 2011, about a month after quitting Elizabeth and James, Taylor met with Shira Sue Carmi, a founding partner of Launch Collective, a company that helped fashion brands with everything from creating a website to launching a business plan. Carmi, now the CEO of Altuzarra, remains one of Taylor’s mentors. “I think a lot of designers prefer to stay on the creative side and leave [the business side] to other people,” said Carmi. “But she's not afraid of the business aspects. And in fact, she really jumps into them very fully. And she's fascinated by the challenges of building a business, of growing a business, of making a profitable business.”

For the first two years, she and McLeod put in 60- to 70-hour work weeks in their tiny office on lower Broadway, often finishing at 2 a.m. Taylor decided she wanted to have her first show in February 2012 at the Museum of Modern Art, which tied back to her line’s art theme. So she called the museum’s restaurant, The Modern. “I’d like to have an event at the museum,” she said. The person who answered the phone told her, “That’s really funny. But there's a corporate sponsor list on our site and each of these people do have the ability to host two events a year, and you could see if one of them wants to host yours."

So she started a campaign of cold-calling all the corporate sponsors. She had no collection to show, but also nothing to lose. Eventually, she convinced a man at J.P. Morgan to give her one of their slots. “He just said, ‘Make sure that the models have clothing,’ and I was like, ‘I promise they will and you're welcome to come. You can bring your whole family,’” she said. After her show, orders started coming in from stores, including Saks Fifth Avenue.

Her life was also changing in other ways. In 2013 she traveled to Little Rock, Arkansas, to see Oscar de la Renta open an exhibit at the Clinton Presidential Library, where she befriended Abedin and Chelsea Clinton. “We’re really close friends,” she said of Clinton, describing their children as “now inseparable.” Nevertheless, by 2014 she still felt as though she was on the fashion industry’s fringes, and so she applied for the CFDA/Vogue Fashion Fund.

Many designers enter for the cold hard $300,000 cash prize, but, Taylor said, “I wanted mentors.” She made it in — along with Wes Gordon, the creative director of Carolina Herrera, who put his own line on pause in 2017 — and was exposed to people like designer Diane von Furstenberg and Vogue’s Anna Wintour, who popped by her studio one late summer morning along with Jenna Lyons, then the lead designer at J. Crew.

Taylor wanted everything to be perfect, so she asked the operator of the building’s rickety old elevator to wear a button-up shirt that day (he turned up in a full suit) and found out Wintour’s coffee order from one of her assistants. Then she had one of the few people now on her team run to Starbucks three or four times to ensure the venti drink was hot when Wintour arrived.

“Either Anna got the wrong information or somebody got the wrong information to Anna, so she wasn’t where she needed to be when she wanted to be there, so Tanya had to get her in the right mood,” said McLeod, who sat terrified in the office during the meeting. “It takes a certain type of person to be able to navigate in front of a famous person like that.”

When Wintour stepped off the elevator, Taylor handed her the coffee. Wintour removed the splash stick and walked across the tiny office to throw it in the trash can. She then looked at Taylor’s rack and offered her advice about how to edit her collection. She didn’t end up winning the top prize, but Taylor, who said she “just didn’t know anybody” when she first moved to New York, was establishing herself in a certain milieu.

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When borders shut down, she was in Canada, pregnant with her second boy. (She married her husband, Michel Pratte, in 2013; the wedding took place in Barbados, where her mother has a home, with Taylor wearing Elie Saab haute couture selected on a “girls’ trip” to Paris.) She only had one pair of maternity jeans with her, so she went to the Gap and bought big white T-shirts to get her through.

Taylor tends to project an aura of cool, but she says she felt “paralysis” as the pandemic worsened, not only impacting sales but also her manufacturing in countries like India, China, and Portugal. “I felt like something I had put years and years of work into was just crashing in front of me,” she said. She calmed herself by having phone calls with Steven Kolb, the CEO of the CFDA, and Paula Sutter, the former CEO of Diane von Furstenberg, as well as her mom, who calls her “multiple times a day” to discuss fine details of the business. “No one ever feels like they're safe,” she said. “It's not like there's a moment where you're like, ‘OK, I'm successful now. I don't need to worry about my company.’”

She gave birth in Canada, and then returned to New York, where she has rebuilt while caring for her two children. “I make Saturdays so creative,” she said. She prepares rainbow waffles from scratch for her 4- and 1-year-old sons, dividing batter into five bowls and adding food coloring. (When I asked her how she has the energy to do such a thing, she said, “It’s actually so easy.”) She and her family then go to an art museum — the Whitney or Cooper Hewitt. When the boys nap from 1:30 to 3:30, she paints, and then posts a video of it to Instagram.

If it hadn’t been for the pandemic, Taylor would have been profitable by now. Outside investment is not out of the question. “I’m sure we’re going to hit a point where we might have to do that,” she said. “I’d love to find a strategic partner who can continue to teach me things.”

Amy Odell is a fashion and culture journalist and the author of the forthcoming ANNA: The Biography. You can read more from her by subscribing to her Substack newsletter, Back Row.

Photographs by Eric T White