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Stylists have a reputation for extreme personalities, often kooky and impetuous or humorless and disciplined. But Rebecca Ramsey, 34, defies any traditional generalizations. Raised in Michigan, she is quick to laugh, humble and straightforward as she explains how she has exceeded expectations — both her own and the parameters of her job descriptions — throughout her career working at Condé Nast, Gap and now at New York magazine, as the newly promoted style director of The Cut. "I try to be really lighthearted and make people laugh," she said about her temperament on shoots with celebrities, models and regular New Yorkers. The positivity she naturally exudes is no doubt related to her success.

Despite her current title, becoming a stylist wasn't her goal when she started her career as a market assistant at W in 2005. In her five years there, she worked her way up to travel the world on high-profile shoots with the best photographers and stylists in the business. After a "Gap year," as she calls it, working for Patrick Robinson at the all-American retailer, she returned to magazines, eager to be on the front lines of fashion week newness again. I spoke to Ramsey before fashion month about how she got her start, the biggest lessons she's learned along the way and why The Cut sees fashion unlike anyone else.

In college, did you know you wanted to work in fashion or magazines? Did you do any internships?

I wanted to be a writer. I worked for the Michigan Daily, which was the student newspaper in college, and I was the arts editor. We did the first fashion shoot ever at the Michigan Daily, so when I was a junior I got an email from Meenal Mistry. Meenal is like my fashion godmother. She worked for Women's Wear Daily and they used to do this thing called the college issue and they would travel and talk to kids about style. Before senior year of college I lived in New York and was an intern at Fitness magazine. When I graduated I was supposed to have an interview at W and I was like, I’m graduating, I can't come! So that fell through. After college I went to the Columbia Publishing Course, which is a six week thing. For the magazine part I was the editor-in-chief of a fake magazine called Eye Candy. It was so funny — I still have it.

What did you do between the program and eventually landing a job at W?

I worked at Elle [as an editorial assistant] for seven months. It was my first job, and I got it through the Columbia Publishing Course. I assisted Miranda Purves, who used to be their living editor. I loved working with them on the home stuff, but I was 23 — I couldn't relate to thread count or silver. I still kept in touch with Meenal and she said, "There's a job at W open, you should interview for it," and so I did and I got it and I was there for five years.

At that point did you know you didn’t want to focus on writing?

I stressed myself out about writing, and I still really wanted to work in fashion. It would be so much more fun to help be a part of shoots, even like just finding things, not being on set. So I jumped at the chance. I started as the market assistant, [and] I managed Paris and Milan. I'd request from Dior and Prada for every shoot and report back to the stylist. I assisted Treena Lombardo, who was the market director at the time. I learned fast.

Alex White was the fashion director and Camilla Nickerson was the contributing fashion editor and Karl Templer — they are all so wonderful and talented and they all have their things they like. I'd learn if I'm looking at a show and something has bows on it, I'm like, Oh, that's great for Alex. We had to make sure brands got shot, and whoever shot the bigger stories or the first ones usually got to pick from the best stuff. At the end of season you made sure all the brands were getting the coverage they need. And I started going on shoots.

How did that happen?

I went on a whole season's worth of shoots with Camilla Nickerson and I went on a bunch with Alex. Even though she had assistants, she would often bring someone from accessories like Shiona Turini or Bei Mandelbaum and then someone from ready-to-wear, me. It was amazing, a lot of travel, a lot of shlepping. I remember packing in the dark in a canyon in Spain for the David Beckham shoot and thinking, I hope I got everything!

Being on set kind of woke up something in me, but I never thought I was going to style. I knew I wanted to do something with a visual contribution. But I never felt like I was going to move up there and I started hearing about these concept jobs — J.Crew had them, a lot of the big brands. And someone at Gap told me about [an opening].

Were you hesitant to leave the editorial world?

I missed it a lot when I was [at Gap]. Your first season when you're not at fashion week and you're seeing it from your computer… it's like total fashionFOMO.

What was your role at Gap?

We were building rooms, like styling rooms, in a sense mocking up collections. I worked for Patrick Robinson. He was a big champion of us being creative thinkers and sitting with the design team, but outside of them. It was helping the designers shape the collection, come up with the vision. We tried to be more open and less literal.

What did you learn there?

How people shopped around the world. That's when I started noticing street style blogs and street style photography, just looking at them over and over again and tearing magazine pictures out. We just ran around the world. We went to Copenhagen, Stockholm, Berlin, Paris a bunch of times, London. We had budgets to go buy things.

Did the program dismantle first or did you leave first?

Patrick left. He was our biggest champion and we were his team. He hired us all. And I just missed editorial, I missed the newness. There was an opportunity at Lucky [as a market editor]. I felt like it was a really great next step to blend what I learned at W and at Gap. Like, Oh, Balenciaga had not worked with Lucky before, we should try to work with them, but at the same time, here's an approachable commercial piece from them without being so fancy.

What was the biggest takeaway from Gap? Did you develop a styling identity?

I don't think I did until I was here [at New York]. I was [hired] to be the first hybrid role between print and online. I would be the fashion editor working with Amy Larocca [New York's fashion director] on our semi-regular series called “Fashionables” and I would work on the two fashion issues with her. I would also do stuff for The Cut — slideshows, fashion week write-ups, market driven stuff — and we had this series called "Out of the Box" and I met my friend [photographer] Erik Madigan Heck by styling one of those shoots. That's when it all really took off and I thought, Oh, I can do this.

I always could see that I could style something, but I didn't know if I had the confidence to do it, having worked for huge names in that world. But online was a new frontier and it was endless pages, too. We could shoot all the brands we needed to but we could also support younger designers because you have all this extra room.

Did you have more space to find your voice with the online shoots?

Yes, I think so and Stella Bugbee [editorial director of The Cut] is such a champion of letting us try things. My first big break in print was Elle Fanning. It was a whole Will Cotton story and it was our fashion issue, spring 2013. Jody Quon, our photo director, and I met Will Cotton and just hung out with Elle Fanning for two days and styled her. She's so cool and just having Jody there cheering me on was like, Okay, I do want to do this, I do like this.

How else did your job change over time?

I started going to Europe, which is something this job never really did. AndThe Cut was getting traction with original photography and street style and we wanted to contribute, we wanted to play the game and we were getting more respect in the journalism world.

I think it was a formalization, but my job did change a lot. I still work on the two [fashion] issues with Amy and in every single issue I work with Stella on The Cut pages. I think I just wanted to do more. I love working with Stella Bugbee, I love working with her team. We all sit together now which makes sense because we're all working on the same thing. Some people write for the site but later on they'll have a piece in the Daily Intel section of the magazine or The Cut pages.

How would you describe New York's fashion aesthetic?

I do think that we don't want to cover fashion in the way that everyone else does. Sometimes all the magazines shoot the same looks and that's okay as long there's a new way of showing it, because also we shoot later than everyone. I think we have a sense of humor at New York magazine. We just ran a story about men's hair and this gentleman Wataru [Shimosato] had butt-length hair and he posed nude with it. Just trying to have a sense of humor and never feel too commercial, but still pushing it.

Was there a particularly transformative shoot at some point in your career that still impacts you?

There's a shoot we did with Tilda Swinton when I was at W. It was Camilla Nickerson and Juergen Teller and [Swinton] played various characters of New York personalities — be it an Upper East Side doyenne, an art collector — all these characters. It was just amazing to help find stuff for that and think about all these different women and pouring endlessly over these characters rather than the clothes. Because I feel like sometimes it happens to me: I love this Gucci collection, I really want to shoot it, but sometimes you think, is it right for the character?

What goals are currently on your mind?

With the new job, I'm trying to bring in more stylists and more photographers to work with us because we can do it all. Now we have the capabilities — we positioned ourselves as a player and we have these relationships with these brands. And that's something that I've worked really hard to maintain with PR and designers. We are also doing more with menswear. And photographically speaking, I want to get more out of the studio. I've done so many studio shoots now, I want to incorporate environments more.

As the The Cut's coverage has extended past fashion, has that freed you up to be less comprehensive or more selective?

We still are comprehensive in that we have reviews and we cover everything from men's to Sydney Fashion Week. But we also cover style tribes, like really niche groups of women who may not resonate with the readers at large, but people would still be interested in seeing them. I feel like you can't do that at other places. I think it's just the spirit of The Cut; we foster creativity, we want to try something new. We won't not try something.Read more at:formal wear melbourne | formal dresses plus size