Rickie De Sole: Editor of Air Mail's Dress Code

Second Life

Rickie De Sole joins Hilary Kerr on Second Life to trace her unconventional yet highly successful trajectory through fashion media and retail. From starting as a

Key takeaways

• Rickie De Sole studied Italian and international business at Georgetown University before landing her first fashion assistant role at Vanity Fair through a mentorship connection.
• Her three-year stint in PR at Prada taught her solution-oriented problem solving and gave her a dual perspective on brand needs versus editorial demands.

Main topics

• Career transitions in fashion media and retail
• Editorial vs. brand/PR perspectives

Notable quotes

"The skillset that is the through line throughout my entire career is that ability to listen, find solutions and get creative."

Conclusion

De Sole's journey underscores the value of curiosity, adaptability, and

Transcript preview

Speaker 2 (0:05) Hi everyone, I'm Hilary Kerr, the co-founder and chief content officer of Who What Wear, and this is Second Life, a podcast spotlighting women who have truly inspiring careers. We're talking about their work journeys, what they've learned from the process of setting aside their doubts or fears, and what happens when they embark on their second life. Today on the show, I'm joined by airmail style and fashion editor, Rikki Desole. Before she joined Airmail, however, Rikki got her start as a fashion assistant at Vanity Fair. From there, she moved into public relations at Prada, where she worked from 2007 to 2010. She then transitioned back into the world of fashion media at Vogue as a market editor, climbing the ladder to the role of accessories director. Rikki later moved over to W Magazine, working her way up to the role of fashion director before transitioning back to Vogue, where she eventually gained the title of executive fashion director of Vogue.com. Although she loved working for publications, she became interested in the world of retail and decided to pivot to a job at Nordstrom, where she ultimately became the VP fashion director. Throughout her career, she also served on the board of companies such as Rent the Runway and Vestiaire Collective. In her most recent move, she left Nordstrom and joined Airmail as their style and fashion editor, where she edits their style publication, Dress Code. Rikki has found so many applications for her countless talents, and I can't wait for you to hear our conversation. Now, on Second Life, it's Rikki Desole. Speaker 1 (1:45) Okay, are you ready? I'm ready. Speaker 2 (1:47) Okay, excellent. So we like to start this podcast at the beginning. So what did you study in school? And much more importantly, Speaker 1 (1:55) what did you think you were going to be when you grew up? I was an international business minor and an Italian major at Georgetown University. I think I always knew I wanted to be in fashion. I had a father who wanted a doctor and a lawyer, and I ended up working in fashion. My sister works in beauty, so clearly that went sideways. But I never studied fashion. I never went to fashion school, but I would always spend my summers interning. And that's how I really found the direction that I wanted to take professionally. But in school, I studied Italian and international business. Do you speak fluent Italian? I do. It's getting a little rusty. We moved to Florence, Italy when I was nine years old, but I went to the American International School. So I speak it well. My grammar is atrocious, but I go back often enough that it comes back. Okay. That's amazing. Speaker 2 (2:40) So talk to me a little bit about your post-grad job hunt. Like what were you looking for as Speaker 1 (2:47) that first full-time professional job? I had interned quite a bit in PR departments. I had interned with Stella McCartney the year she started her business. I was sort of on the PR team, but when you're starting businesses, the PR intern does basically everything. It was a lot of boxing and unboxing samples. And I had also done the Condé Nast internship. And so I think that's where my love of magazines really started. I was Tani Goodman's intern. Amazing. I know, I know. I love Tani. You know, she is still to this day such a mentor and someone who... is so kind and gave me so much time and really, you know, brought me on shoes and I learned the ins and outs of magazine making. So I knew pretty soon after that internship experience that I wanted to get back into magazines. And there's a wonderful woman, Elizabeth Saltzman Walker. She was at Vanity Fair at the time. She was living in London, but she... helped me get my first job, which was at Vanity Fair as a fashion assistant. I worked in the fashion closet, no windows, surrounded by samples, but I wouldn't have traded for the world. But I really owe Elizabeth that first job. Speaker 2 (3:51) She is an amazing person and an excellent interview as well. Talk to me a little bit about that job. What is your day like? What are the skills that you're honing? Speaker 1 (4:00) I think in those roles, it is so much about building a Rolodex, right? And so I was communicating to other interns and other assistants and sort of calling in samples. So I was the assistant to Alexis Bryan, who was the fashion director, market director at the time at Vandy Fair. And so much about that. phase of being an assistant is absorbing what's happening around you. And so working with Alexis when she had market pulls, when we had stories, we worked with Sarah Jane Hoare, Michael Roberts was our fashion director at the time. He was living in Brazil, so we were always doing shoots in Brazil, which involved a lot of packing of samples. But I think just being exposed to the talent that was there and seeing how they navigated the industry, sort of understanding what brands mattered, what brands didn't matter, I think was where my interest was piqued. I also spent a lot of time on set in those days. So I would take the trunks and I would also go to set and get to unpack them. But being able to watch the magic unfold, we shot so many celebrities at Vanity Fair in those days. So it was just being around and being able to sort of observe as I'm steaming clothes and doing all the granular work that someone has to do. I Speaker 2 (5:06) do think Speaker 1 (5:06) there's something Speaker 2 (5:06) so important, though. I think back to my assistant days, and it's like, if you're not going to get the lunch order right, if you can't Xerox this correctly, if you can't drop this copy off on the appropriate person's desk, if you can't do the minutia, no one is going to trust you with doing more. I'd had so many internships by the time I got a full-time job. I felt like I was so overqualified for it. But building that trust within your organization and having people understand if they can hand you something, it gets done. That is such a foundational, important part of anyone's career. And I think that people sometimes poo-poo that side of it. And I was like, no, that is everything. And you will continue to find ways to do that. And like those skills of like that level of detail and follow Speaker 1 (5:52) through will serve you for the rest of your career. And I think also it's about how to build trust with the messenger center, right? Because inevitably, you know, they give you a cutoff time, but you haven't made the cutoff time. And I think learning how to build up a rapport that they know that you've tried your hardest to get there by whatever hour they've told you, but kind of being able to get in with them to say, you know what, just do me a favor, right? Like, help me help you. So I think learning a lot of how to navigate those situations and know when to push and when to pull. I think this industry is so built on relationships. And I really started building my Rolodex those early years at Vanity Fair. There were other assistants. You know, I sort of made these friends. We were in the closet together and we made these friendships that have sort of served our whole lifetime and our whole careers. We've kind of grown up together. I Speaker 2 (6:38) have some of those trauma bond relationships too. That's exactly the way to describe it. Speaker 1 (6:43) So how long did you stay? in the fashion closet? I was not there too long. I was at Vanity Fair about a year. If memory serves me correctly, I also did not have benefits at the time. And I think like all assistants, you sort of just get the first opportunity. You sort of use that time to prove yourself, but also wanting to have benefits felt like a priority at the time. And an opportunity came up to go to Prada to do public relations. And I had interned quite a bit in PR. So I understood what that world was like. And I moved to Prada, I was a PR manager, I believe, in the New York office. If you're going to do public relations, you have to love the brand that you're representing. And for me, Mrs. Prada is the greatest living designer of this era and getting to work within her orbit and with that product really felt like the right move for me at the time. Speaker 2 (7:33) So I remember back in the day, there were lots of theories about like, well, if you worked in features, you couldn't move to fashion. And if you worked on print, you couldn't move to digital or vice versa. And that if you worked in editorial, you didn't want to move to PR. It didn't feel as open back then. Were you worried at all, if I move from editorial to PR, I will now have set myself on a trajectory that will just be PR? in perpetuity? Or did you feel like this is just a step and I can flow back? I don't know if I was that strategic Speaker 1 (8:07) at the time, if I'm being honest. I think for me, I felt it was imperative to keep learning and keep growing and maybe to, I don't know, get a window. Speaker 2 (8:17) A window and benefits. Those are important things. Right. Speaker 1 (8:20) Gosh. So I think it was early enough that I felt that it was a step to see the other side, right? So actually what was interesting about my pivot from that fashion assistant role into a PR role was I was on the other side of it. So now I'm flip side and I understand what a brand wants out of a photo shoot, what a brand is looking for in a press release, what a brand is looking for from an event. And then I also understood what was happening on the magazine side that they were actually calling it. 20 brands and only one was going to get chosen. You know, really understanding sample management from both sides. If I had to sum up my time doing samples and working at Prada and working at Banny Ferret was finding solutions. You've one sample set that has to get to 15 September cover stories, and you have to figure out how you're going to share samples across all of those. So for me, it was getting me back to Italy, which I was really excited about. I think for a long time, and maybe it's changed now, but the Italian offices were sort of always like the Americans, you know, and I think I was quite successful at Prada because while I'm American, I understand Italian, my father's Italian. So I think they sort of felt like I was one of them. So I was able to cross the lines a little bit more. And really, I loved what I got to learn and spend time at Prada because we were doing projects and just getting to be a small part of that opened my eyes to how creative you can be on the brand side, in addition to being creative on an editorial side. So you were there for about Speaker 2 (9:44) three years. What do you think is the most important thing that you learned during your time? What was the biggest takeaway? Really that finding Speaker 1 (9:52) solutions mentality and being nimble and sort of trying to say yes as much as I possibly could because we were trying to maximize the collections and maximize the visibility. Also the networking piece. So suddenly now I'm talking with all the editors, whereas before when I was at Vanity Fair, I was talking to all of the brands. And then now I was on the brand side talking to all the editors. And that's where I really continue to build that Rolodex. And also it's funny, the number of people that worked at Prada in the years that I was there really built up my network in the industry. Yeah. And everyone's always like, how do you know so many people? I'm like, because I worked at Prada for almost four years and I got to meet the head of wholesale. I really understood the type of roles. exist within the brand beyond a PR role. Speaker 2 (10:34) Prada also attracts major talent. So even as those people move on and leave and go to other things in their career, they're not leaving to go and become regenerative farmers, generally speaking. They're staying within the industry. And now you have someone who's like excellent and now just somewhere else. And so then it's like the world is even more open because. all of the excellent people you work with are now working other places, which is Speaker 1 (11:00) useful. It's so valuable to me. And then because I was at Prada, I worked a lot with the Vogue team because they were constantly requesting Prada samples. And I remember very distinctly, there was one Thanksgiving when no one was available. I was still in the city. So I went back to the office, I got the lookout. And I think that was sort of the defining moment where they said that girl's willing to go the extra mile. Speaker 2 (11:21) So talk to me about your next step, which is you went to Vogue. How long had you been thinking about maybe my time at Prada is coming to an end or maybe I should start looking for something new? Or was it really just like this relationship was so incredible Speaker 1 (11:37) that you decided to take a leap? I was not looking to leave at all. I loved my time at Prada. I really loved doing PR and I thought that that was my path. Timing is everything in life. I am a true believer. I got the call from Vogue. I remember going in for the interview thinking Vogue wants me to work there. I think I should probably take this seriously. And I got to know Virginia Smith, who ultimately became my boss at the time and is a dear friend. And we'd worked together, like I said, on a lot of shoots when I was at Prada. And it was a really hard decision for me. I think part of me really wanted to stay at Prada. I was very close with the team there. A lot of them are still there and I'm still very close with. But I thought this was an opportunity that I couldn't pass up. And I have this philosophy whenever these opportunities come that if I'm going to regret it, I have to do it because I can't spend my life thinking, what if? And so I took a leap of faith and it was hard. And my mother would probably regale you with stories about how much I panicked about the decision or questioned my decision. And, you know, starting a new job in Vogue in those days, it took a bit of... adjusting and reacclimating when you come from a role that you really loved. But I had to sort of trust that I was going to keep growing and keep learning. And that was part of the process. When I joined, I joined as a market editor. And these were the glory days when we had so many market editors that we split the right of our market. There was a market editor named Jessica Saylor, still a dear friend. And she had contemporary brands A through M. And then I had contemporary brands. N through Z. And we'd be at a showroom and you'd be like, sorry, that's not my brand. And then I did the sustainability market. I did the bridal market and a few other random things. But I became an expert in those brands and in that field. And so I was out at market appointments all day, really familiarizing myself. And that got me working with Tani again, because Tani used to have a page in the magazine in Vogue that was dedicated to sustainability. How did Speaker 2 (13:35) you get up to speed? Because this feels like a little bit of a different beast and a different skill set. And also, I mean, bridal alone is its own massive specialized world. So how long do you feel like it took for you? to really get up to speed? And what were some of Speaker 1 (13:52) those learning curves in the early days? I probably ran around like a crazy person. I would take pictures of everything. I'm a very visual learner. So anytime I was at a market appointment, I'm sort of snapping photos, trying to remember everything. You sort of ask the right questions, you know, with PRs, really becoming friends and spending my time meeting for breakfast or meeting for drinks after work to build up that network so that people would call me to sort of say, we've got the new brand, you have to come see it and starting to trust. recommendations from certain people. I'll never forget in those days, fashion week would roll around and you would be given the grid, which the grid was where they would put all the editors at the top and they'd write down all the