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Taylor Tomasi-Hill Has Always Been One Step Ahead of the Fashion Industry's Evolution

Now Creative and Fashion Director of The Yes, she talks going from publishing to e-commerce start-ups and how her brief floral hiatus helped shape future job requirements.

In many ways, Taylor Tomasi-Hill's career has evolved with the fashion industry, her resume reflecting how the tides — and perhaps more consequentially, the power brokers — have shifted. 

She was a magazine editor at the time when it was peak-glamourized in the popular imagination, when names on mastheads were starting to become street-style favorites. (Tomasi-Hill, with her penchant for prints and bright red hair, has long been a favorite subject of photographers waiting outside the shows at fashion week.) She left publishing to work in e-commerce in 2012, for a then-barely-year-old company called Moda Operandi. She got brick-and-mortar and specialty experience at Forty Five Ten, before eventually landing at The Yes, an AI-driven shopping app that started getting headlines months before it even went live because of a cool $30 million investment from Forerunner Ventures, True Ventures, NEA and more.

Tomasi-Hill always had a connection to fashion, given that her parents owned a successful children's accessories showroom in Dallas. But she says the industry wasn't something she followed all that closely. "I went to art school and studied industrial design," Tomasi-Hill tells Fashionista over the phone. "By junior year, I thought I was going to graduate and become a furniture designer, but [the school] implemented a rule of having an internship in order to graduate, and I ended up going to work for W."

It was the early 2000s — "the height of the magazine," Tomasi-Hill remembers. And for the next decade, she'd have a front-row seat at the evolving job description of the fashion editor.

"When I started in 2002, it was very much so that editors were behind the scenes. Now, it's very different: Editors are very forward-facing and brand-representative; some are influencers, some are more influential for publications and for brands," she explains. Also, at the beginning of her career, "there wasn’t an advertiser checklist on [set]," she remembers — by the time she walked away from publishing, though, "[you were] basically being told what you have to put on the page."

Over the years, Tomasi-Hill worked at W, Teen Vogue and Marie Claire. And even as an editor, she found herself deviating from some of the established (or expected) parts of the job, largely because she didn't really see the point. For example, "I felt like it was a waste of time to sit at eight to ten shows a day — but I had heard of all of these trade shows that really only buyers went to," she says; so she asked her boss at Teen Vogue to let her go to those instead. That allowed her to identify emerging brands that she could feature in the magazine, and "it became my passion. I found what I really loved to do was help and mentor these young talents."

It was around this time that Tomasi-Hill began noticing other incongruences in the fashion system. She recalls having conversations with fellow senior staff at the end of fashion month, where they would discuss what stories they wanted to execute and products they wanted to shoot based on everything they’d seen on the runway in New York, London, Milan and Paris — but seeing a disconnect between what pieces the editors highlighted and those the retail buyers actually placed orders for. Many times, she says, they'd try to call things in only to learn that they hadn't been purchased at all. It's no surprise that her next move was to go to Moda Operandi, in 2011.

Tomasi-Hill's role as Creative Director at Moda Operandi was meant to be a solve for the issue of having both a buyer and a creative liaison, where "the buyer goes and buys, then they dump [their buys] on the creative and say to do something cool with it, without any context." It was also an opportunity for her to get digital experience, something she hadn't really had in her decade in publishing but understood would be important in the changing fashion landscape, particularly when it came to retail.

"I knew I had something to learn, and I think a job is much more interesting when you have things to learn, as well as to contribute."

Moda Operandi was a crash-course in data and analytics, she says, which confirmed to her that she wanted to work in fashion roles that married the quantitative and the creative. But after a while, she got burnt out.

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"I was working at a startup. I was not only the creative director, I was overseeing all editorial and buying. I was traveling [many] months out of the year for shows and, on top of that, I was in Abu Dhabi and Dubai, Brazil — all over the globe, educating the customer on what pre-order was and what Moda was," she explains. "It got to the point where I didn't have clarity around what I was actually passionate about anymore. I felt like it was better for me to take a little time away and figure out what I really wanted to do."

This chapter is perhaps best known as TTH Blooms, Tomasi-Hill's flower business. Though it was a hiatus from a "traditional" fashion role, the plan was never to leave fashion, she's quick to clarify: "It wasn't supposed to be that I was leaving forever. It was really to help me reset and understand whatever I was going to do." However, it did shape the way she would pick jobs moving forward.

The origin story of the company, which Tomasi-Hill worked on for two years, goes like this: She was taking meetings with brands like Diane von Furstenberg and Tory Burch right after leaving Moda Operandi and would send her own floral arrangements as a thank-you — those caught the attention of the right people, and soon enough those very brands began commissioning her for events.

"It very quickly turned into a big business out of my kitchen," she says. "My husband did not love that I brought two floral refrigerators into my apartment."

Not long after, Tomasi-Hill learned she was pregnant, so she didn't necessarily want to be interviewing for full-time positions. And TTH Blooms provided steady creative work that kept her close to the fashion industry, so it didn't feel as pressing of a concern. More consequently, it solidified a set of non-negotiables she would need from any future employer.

"Every job that I have taken on, there has always been one thing that I'm very upfront about, and that is that I don't want to just be the face of a brand," Tomasi-Hill says. "I don't want to just be sitting at fashion shows all day. I don't want to spend my time just at dinners with the same people for 30 days four times a year. I don't want to be away from my family that long. I'm happy to travel, I'm happy to be involved in the industry, but there's a way to do it where you can do both." 

In addition to that, her role would need to have some involvement in the business side of the company, and it would need to play a role in promoting brands. That was true of Forty Five Ten, where she was VP Creative and Fashion Director from late 2015 to early 2018 (and the gig that moved her and her family to Dallas, where she still resides), and it's true of The Yes, where she's been since the summer of 2018. 

Tomasi-Hill met co-founder Julie Bornstein not long after she left the Texas-based specialty retailer. "It wasn't even an interview — somebody connected us and we were just talking about what she was doing," she says. "In our one-hour conversation, I knew she was a woman I wanted to work with."

Now, she's the shopping app's Creative and Fashion Director, where she says she's able to do what made her so passionate about her job as an editor years ago: Help brands grow. 

"We're going witness so much change in the next two years, next few months, next few days — everything is changing hourly, but I would say what's exciting right now [about fashion] is that I think this is the time we do get to reset," she explains. "We always talk about what needs to change and we all have ideas, but now it's up to the brands to implement them. I think we're gonna see a lot of brands struggle, but I do think that we will see a lot of brands taking control. We're giving brands back the power and truly partnering with them. We have technology to change the way we shop online, and that's why I'm with The Yes."

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