She’s outfitted everyone from Oprah to Michelle Obama, with a lauded designer line and a successful affordable counterpart at Macy’s, but few founders have been as battle-tested, bold, and brave as Rachel Roy.
After bouncing around retail jobs at Neiman Marcus and BCBG before landing an internship at Rocawear, where she rose to the role of Creative Director for Women, it was in 2004 at age 30 that Roy decided to strike out on her own. A buyer at Bergdorf Goodman gave her her first order. “From there, it was self-funded,” says Roy. “I was still working; it was not a startup with me in my kitchen.” In 2007, with the help of her first financial backing, she expanded her designer Rachel Roy line to include a more affordable, RACHEL Rachel Roy label. Two years later, after a grueling divorce, she said goodbye to her corner office and 50 employees in New York to move to Los Angeles with her two daughters and their dog in tow. “I walked away from a lot,” Roy says of her decision to leave New York. “I knew it was the right thing to do…putting your kids first doesn’t mean you are not a good business person. It means you’re a good parent.”
Over the next six years, she worked remotely, leading her team from afar while learning to relinquish control—until 2015 brought a lengthy legal battle after business partners tried to sell her trademarks and liquidate her design assets. Roy prevailed, ultimately winning her name back based on a single, strategic line she placed in her contract. “I always knew that a group of men with money would assume the role of decision-making and power,” she admits, adding, “I observed mostly men starting businesses in my adult years, but I never thought for a second that a woman couldn’t do it, too.” Now, Roy is finally looking toward the future and what she wants to do next—post-pandemic, in charge of her own name, and free of limitations.
Financially, how were you able to branch out on your own and start your brand?
I launched officially in 2004 but had been working on it quietly for a few years, making samples where I worked, which saved me a lot of money. I only need several thousand of my own, and then I funneled as much of my earnings as I could into my own business. I had also been able to observe exactly how to start a business—because that’s what I had been around for the seven years prior at Rocawear. I learned the garment business, the licensing business, I learned the schlep of it all. It was my job to make sure licensing companies were not creating products that were not approved by the company, so I had to deal with men yelling at me, trying to scare me, hiding things from me [laughs]. Although it wasn’t my ideal position, I respected it. It got me used to what business on my own could be like.
When starting Rachel Roy, did you have experiences with a lot of men trying to muscle you or other forms of sexism?
Oh, always. I am a woman who likes femininity, likes beauty, has really good taste and knows that about myself. And yet, I never wanted to be judged or taken advantage of because I like red lipstick. I never apologized for liking to look very feminine, sometimes sexy, and expecting to be taken seriously. Some of that could be credited to observing men in my earlier professional years, but really the credit goes to having a very stubborn, very proud immigrant father.
Anyone reading this who has been raised by Indian immigrants will relate. My mother is Dutch, but my dad really ran the house. Indian immigrant parents just expect a certain level from their children, and it made no difference that I was his daughter versus his son. That pride you have from an immigrant, demanding a certain level of excellence at a very young age, is empowering. That’s where the “I am who I am and I don’t have to change for you” attitude came from. I observed mostly men starting businesses in my adult years, but I never thought for a second that a woman couldn’t do it, too.
Did you always know you’d prefer to go it alone, but needed partners to get your business off the ground? Or was that something you learned along the way.
It came to a point around 2007 that the only way I could keep the business afloat was to find some partners and I did. I got [the late] Marvin Traub, who started Bloomingdale’s and he was someone who had been in retail for so long, and I felt he really understood it. I had always been raised to have a lot of respect for my elders, and he was at that time. If I wanted to expand, I knew this was an opportunity I should probably take. So from there, we went to The Jones Group, which had Nine West; they wanted to be an American LVMH. They asked me to bring in some of my younger friends from the CFDA, which I did, and then they got taken over by another company that was lousy, that all dissipated, and I had to find a new partner. It was years of learning things I never wanted to learn at all, and wish I hadn’t had to. But it’s the cost of doing business. I could have worked for a larger company and been quite safe, but I took the route of independence that I probably learned from my father.
You’ve always been so centered around female empowerment, and I read that your company is heavily composed of women.
At one point, right before I left New York, there were about 50 employees in my office working on my brand, and 49 of them were women. It’s not that I was telling my management staff they could only hire women, but if they were available and they were qualified, I wanted them. That was the type of company I wanted to run and give to my daughters one day. And that 50th was gay, by the way [laughs].
Shop RACHEL Rachel Roy
You decided to move to California in 2012, after years thriving in New York. What was behind that decision?
I made a determined decision to leave New York and bring my daughters to California simply because there was more space for them and a better quality of life. I would have had to get quite far outside Manhattan to have provided for them what I am giving them in California. With that comes losses for the business, and yet gains for your children. How do you measure that in terms of what is ‘successful’? Do you say, “Okay, we didn’t open the stores because I wasn’t physically present in the offices in New York”? Or do you say, “I see lots of gains with my daughters”? I chose to take the standpoint of measuring it by what’s healthiest with my kids.
It took me about three years to really be firm in my decision and know, Okay, this is just what I’m going to do. I started a mood board in the same way I do when I start a collection. I noticed a recurring theme was homes with water and the ocean. I knew that if I was true to myself, and listened to myself, I would follow that. It was a gut instinct, listening to that inner voice. That is exactly what design is, too. That part of my job, both as a designer and as a mother, isn’t difficult. There are a lot of things I second guess about myself, but never that inner voice—it’s what guides me. I can always go back to New York and pursue business from a different, more ambitious standpoint once they’re in college. I’ve felt because many of my customers have children themselves, my decision might either provide comfort or reassurance that putting your kids first doesn’t mean you are not a good business person. It means you’re a good parent. The business is there to supplement life, not business being life. I had experienced years away from the office long before the pandemic happened. It’s not ideal, but it’s doable. And as my daughters’ situations switch, I may end up going back to the city.
We’ll touch on the pandemic soon, but first, how has it been living so far from where your main Rachel Roy offices are located?
It was extremely frustrating at first; things were not getting done the way I believed they should be. It was a lot of letting go, saying to myself, “Okay, I can’t do everything at the same time; I can only do one thing really well at a time.” So, whether that’s taking care of myself at that moment, taking care of my daughters, struggling to get orders in, working on management—whatever it is, I can only do one thing at a time; that took me a while to realize.
I learned from a Deepak Chopra lecture that no one is good at multitasking. It was mostly women in the audience during this particular talk, and you could hear a hush go over this very type-A crowd the moment he said it. For many of us, that’s how we’ve survived as adult women: working, taking care of families. But when I moved into that reality [that no one is good at multitasking], believed it, and felt pride from it, that’s when I felt a shift. Instead of always having that struggle mentality, where it was always a race to catch up, I felt almost a regalness in the pride of my decision to put my children before monetary value and the ego of success. Then, everything sort of fell into place. Yes, I had to give up a lot. Some things slid by that I didn’t agree with—styles, colors, fit, all of it, everything you can imagine not liking was disliked by me at one time or another after the move—and yet I was proud of myself. From that shift, a lot of people started coming into my life with like-minded values.
I put my children before monetary value and the ego of success.
I met Nobel Peace Prize winner Kailash Satyarthi, an Indian man who has saved more than 85,000 children from trafficking, mostly little boys in slavery working in factories. I traveled to New Delhi, India, and stayed at his center where he rehabilitates the boys he rescues to learn more about how I could help. I was so moved after learning about how these products are made that I wanted to make a shift. It is the part of fashion no one likes to think about: we like to design and create, but who wants to really think about where these patterns get made? Once my eyes were open to this, I really saw a huge shift in how I wanted to produce.
What changes did you make in response to that internal shift?
I was told by partners not to speak about it in public. But I have friends who work at Women’s Wear Daily and even in a friendly manner, I could say, “Hey, please write about this.” If it had something to do with fashion, like how clothes are made in these factories, they of course would. I just wanted awareness. It seemed silly and fearful and, quite honestly, unevolved to spend time pointing the finger or blaming. For example, Lorraine Powell Jobs produced a documentary about Kailash [Satyarthi] and his discovery that child slaves were making products for several big-name brands. Kailash could have gone on this shaming, finger-pointing campaign, but in his mind, he said, “I’d like to assume these companies don’t know,” and that is such a fair statement on his part. In the design world, we hire production. We trust them fully to execute. It’s not our area of expertise or even something we could cite facts about. There’s a long list of compliance rules we produce that these factories sign off on, and we think that’s the end of the story. It’s not the end of the story, because the agents we are hiring overseas to be the middleman [to represent us and the factories] are often paid by the factories and become double agents. Much of the work that is done by children, we don’t know about it and think it’s not happening. Kailash took that approach with these companies—and these are large companies, the two that are mentioned in the documentary. Like Maya Angelou says, “When you know better, you do better.”
The film initially wasn’t getting a lot of traction, and so I brought it to the MoMA where my brother is the chief film curator; I brought the film to Parson’s, I also brought the film to the White House, and I screened it in California. I chose Parson’s in particular because I wanted young people who were about to go into the fashion workforce to know what was happening on the other side. Many of them will be in the position to make better decisions in production.
What was it like disagreeing with your partners over something so important to the brand, like how clothes are made?
We did not have shared values. They did not want me to speak about Kailash or my work with him or what was going on in the factories. But as frustrated as I was when my partners were not agreeing with me, I had done enough Deepak retreats that I knew it wasn’t about me. It was about them, and the amount of information that they had encountered in their lives. I knew I had to make a shift. Of course, I choose to talk about it. I did a campaign and took [the film] to as many high-profile places as I could that I thought would write about it. It was not in defiance, it was following that inner voice of what was right.
I’ve been through many different legal battles over the years with partners, and it’s just something that comes up. You’re either okay walking through the fire to do what you believe in, or you choose that it’s too much for you. I have friends who have been at the same company with me, owned partially by the same owners, who have decided not to fight for their name. And that’s fine, too. Really, the customers never know who fully owns your company. With Rachel Roy, I ended up buying that back and own it fully now; I can do whatever I want with it. That’s the answer when someone doesn’t agree with you, it’s the Gandhi approach. You do what you can, within your own means. Don’t point the finger. Don’t shame them. They have their own journey. With whatever’s in my own means, I am an entrepreneur at heart, and my spirit is to not ask people for things. I don’t like borrowing money. I don’t like having partners if I don’t have to. So you just take loans out and do what you have to do.
You mentioned you first brought on partners in 2007. How did that help your approach to business in 2008 with the recession?
In 2007, I started looking for partners and in 2008 when the recession hit, I had already found a partner in The Jones Group. Ironically, they only wanted to sign if I was willing to make a line for Macy’s, and I agreed to that before we went into business; it was all in the contract that I would do a secondary line for the department store, and they would fund Rachel Roy, my designer line. The fortunate thing at that time is that The Jones Group had so much money, they did not care if my designer line made money. That is how much money this company was generating. So it was a very rare time in America, with very rare partners who said, “Do whatever you want with this amount of money for your designer line, all we care about is the secondary line and Macy’s”—because that was their partner with their other brands, like Nine West.
I was told by a stylist that if she put in as many brown girls as I was requesting, I would not be taken seriously by Vogue.
It worked at the time because the recession in 2008 was not as big as what I believe will happen now. Yeah, it was a recession. People needed to save money, but they didn’t need to save as much money as I believe they are going to have to save now. And so they very much appreciated a secondary line; in fact, a lot of people thought it was brilliant. Writers really supported the fact I was coming out with a more affordable line right at the time people needed to spend less on clothing. I had designer friends telling me, “Don’t do it; it will be the death of you.” Again, I trace it back to how I grew up. In my small town, Macy’s was the most expensive department store there was. I would have had to drive 90 minutes to hit a nicer department store in the San Jose or San Francisco area. So I didn’t have a problem with RACHEL Rachel Roy. I knew I would do well by it because I wouldn’t just phone it in. I would design it, I would want to wear it, I would try everything on. It was successful in the midst of a recession because I was making well-priced, inexpensive clothing, but putting my heart into it and respecting the customer. Cut to what’s happening now with the pandemic, and it’s a completely different story. I can’t do that now. People don’t have enough money for themselves and food, let alone inexpensive clothing.
Where is your head at now with the current pandemic situation?
I am re-looking at what I want to design with my designer line, Rachel Roy, which has been asleep for a while. The Jones Group dissolved, and my partners after The Jones Group didn’t want a thing to do with Rachel Roy, so it hasn’t been in existence for quite a while now—too long. Instead of focusing on clothing, which is the given, I want to focus on the other forces. It’s not going to be made by children. It’s not going to hurt the environment. My daughters and I stopped eating meat in 2017, so animal welfare is really important to me. It needs to check those boxes because that’s where my head and heart is at right now. But product-wise, I want to deliver a product that is needed and not stuffing something down someone’s throat at a time when the country cannot even afford it. You hear about slow reopenings with states? It will be a slow reopening with Rachel Roy.
My secondary line, RACHEL Rachel Roy, has stayed in existence since inception and is still doing well—knock on wood. But it is suffering business-wise with all the shutdowns. No one can predict what’s going to happen. What I can predict is my behavior with it. I want to be really respectful, even on social media with what I try to sell. How important is selling something right now, even? I try to pick a product, and put it on myself, and explain why it’s helpful; I sell optics with my secondary line. But it’s really important to me to watch my tone as we move through this [crisis] because I deeply respect my customer. Not only that, but I feel like I am my customer; I understand struggle and it’s heartbreaking. I want to be very careful with that, and I just have to wait it out. There’s no other way when so many people are in pain. I see this very differently than what I went through in 2007 and 2008.
It’s never easy to see business plans collapse, and employees worry about how they are going to make a living. There are really tough decisions going on right now. But since everyone in the world is going through this at the same time, I got into the mindset quite early on that this is a fire that needed to be walked through. For quite a while now, I have wanted to see sustainable changes in fashion in general, and in fast fashion in particular, so hopefully this will bring around those changes in a worldwide way instead of one brand at a time.
You’ve run your company through more than 15 years of ups and downs. Do you have any thoughts on leadership through this time of so many unknowns?
I don’t like being a leader. When I say that out loud, I don’t know if I’m hurting or helping my company and other women, but it’s not something I enjoy. Being a really good leader, I think, takes a bit of that Bill Clinton effect. Of course, you have to be intelligent. You have to be smart in what you are trying to lead. But you have to be charismatic. You have to be charming.
My father was a professor of sociology. He used to make my brother and I go and sit in the back of his classes. When a student couldn’t answer a question, we would have to stand up and answer the question. At a very young age, I learned that sociology is what you make it; if you can defend your answer it’s correct—there is no black and white. In running a company, you realize from the beginning that nothing is black and white, it’s all in how you arrange the argument or position you have. Then, can you get other people behind that and also do it without hurting feelings? It becomes very taxing to worry about how people feel, as someone who wears her heart on her sleeve and greatly cares. It can be so tiring. I would much rather someone else lead, but the times in my company where someone else led, I was not successful. So there’s this combined realization that I both have to lead and don’t like to lead, and part of the move to California eliminated some of that tension.
It’s important to watch my tone as we move through this [crisis], because I deeply respect my customer.
That was the sad part of starting a business; the amount of time I actually designed went from 100 percent to 20 percent, and, for a while, I resented it. I kept thinking, How can I get back to just designing? Well, you can’t. If you have a business, you have to run it. That’s partly why I’m okay with taking things slowly while I am raising children. To be a good leader, you have to bring 100 percent. You have to be inspiring. You have to be encouraging. You have to be a bit of a counselor. Again, going back to that Deepak statement, you can only do one thing at a time well. Am I going to counsel my children or am I going to counsel my employees? It’s a balance.
It’s so interesting to crave this autonomy to create the things you love, but with that autonomy comes a whole other set of baggage.
That’s right. And I’ve been navigating the baggage since 2004. I am doing an okay job at it [laughs]. But you know, the older I get, the more confident I get, and the more I realize what I need instead of what I thought I really wanted. Designing is my favorite thing to do; leading and running a company is my least favorite thing to do. If you talk to business owners who come out of Silicon Valley, it’s very different than talking to a designer who owns her own business. A lot of us never wanted to start a company, grow a huge unicorn that could be sold for however many times the initial investment. I never had ambitions to sell this and make a huge profit; I wanted to work in a field where I knew I could offer something to women who had lives like myself and had body shapes like myself. I’m so proud of being one of the first designers in the CFDA to start a plus-size line, which I called “Curvy” out of respect. I was very curvy with both my daughters, especially my second pregnancy, where I gained 80 pounds. I don’t think all female founders are the same. We are all quite different in our approach. But my end goal is to design beautiful products.
Any last advice for female founders looking to start or grow their own business right now, in this wild time in the world?
If you do need partners—and you probably will over the course of your career—put into the contract that you are “100 percent in creative control” of the company. With my partnership with The Jones Group, that one sentence got me my name back when the company that took over The Jones Group tried to take it away. I had friends who did not want to fight for their name, but I did and I went to court in Manhattan, fought them, and that one sentence gave me the right to decide what to do with my line. The judge said, “Creative control means you can pick who you want to sell your company to.” And now, forevermore, that judgment is in the books and I am really proud of that. It is something that is really important to have when you are working with partners that perhaps do not have shared values.
That gave me chills. I’m guessing a lot of founders, especially creative founders, don’t like dealing with contracts. The language can be so tricky.
Yep, “100 percent creative control.” I never asked for control of the money. I knew if I designed a good product, I would eventually make money. But I learned to add that one sentence in there because of all the time I spent working with the licensees in my previous job, walking up and down Seventh Avenue, trying to make sure these men designed products with signed-off approval. I just thought, you know what, let me put in there that I am the only one in control of creative—because “creative” ends up meaning fonts on a website, what models you choose in your shows. I was told by a stylist for one of my very first shows that if she put in as many brown girls as I was requesting, I would not be taken seriously by Vogue. I mean, this is how much of a dinosaur I am, because that’s obviously not the case now. But all those decisions, at the end of the day, the buck stopped with me creatively, and I always felt that was so much more important than the finances with a line with my name on it.
*This interview has been edited for length and clarity
Jenna Birch is a freelance journalist and author of The Love Gap. Her work has been published in The Washington Post, Vogue, Harper’s Bazaar, ELLE, InStyle, Fortune, Man Repeller, and more. Read more of her work here.