‘I only put her in things other people had worn’: Law Roach on his Zendaya styling strategy 

Celebrity stylist Law Roach is known for creating iconic red carpet looks, from dressing Zendaya as Cinderella in a Tommy Hilfiger dress that lit up with the wave of Roach’s wand to making Anya Taylor-Joy look like Eliza Doolittle in vintage Bob Mackie. In March 2023, he shocked the fashion world by announcing his retirement from day-to-day styling. Now the ‘image architect’ has reemerged with a new business, an online learning platform called School of Style, intended to help aspiring stylists navigate the exclusive and opaque fashion industry. Roach will serve as chief creative officer for the platform. He stopped by the Most Innovative Companies podcast to talk about what he hopes to accomplish through School of Style, how he helped Zendaya stand out, and what Kamala Harris could do to up her style game. 

How did you get your start as a stylist?

I opened a vintage store [in Chicago in 2009]. Kanye West came in, and [the store] just kind of exploded. We started to get calls from stylists around the world in London, Milan, New York, and L.A. asking for things. I just started saying I was a stylist. I don’t know if I knew a lot about fashion, but I knew about style, because style is what you’re born with. I did more and more research and a lot of diving into magazines and YouTube, trying to learn as much as possible.

How do you create a look?

For me it always starts with the emotion. I have to figure out who the client is, and then, as I start the process of pulling a look for a client, I have to [see] if the clothes make me feel something. I started to think of myself as a storyteller as well. I found that people enjoyed it when there was some type of reference point or narrative. [It’s great] when you have a client like Zendaya, who is one of the best at becoming whatever that character is. For example, at the 2018 Met Gala, Zendaya went as Joan of Arc wearing Versace. Her face, her stature. She knows how to embody the character from whatever story we build.

Your references come from all over the place, from the Beyoncé “Crazy in Love” music video to Joan of Arc to My Fair Lady. What kind of media do you consume?

Social media has made the world so much smaller. You’re able to find pages that feature references from the ’80s or ’70s or the Baroque period. Then you kind of dive into a rabbit hole and mentally bank some of the images.

Why did you want to revive School of Style?

My ultimate goal is to shrink the gap between dream and reality. There are people all around the world who aren’t in New York or L.A. or Paris or Milan where the industry is readily available. So people anywhere can sign up for coursework and become an active participant in the fashion community.

The School of Style curriculum includes classes on setting up a business. Why is it important for you to teach people how to handle their finances?

When you’re a freelancer, if you don’t come from a place of financial literacy, you make a lot of mistakes. My first year of styling I made $120,000 and I thought that was really good. I spent like I made $120,000. I was living in Chicago, but lying and telling people I lived in L.A. I was reinvesting the money in my business. But actually because I was a 1099 employee, it hadn’t been taxed. After a couple of years I slid in my ATM and the balance was zero. I went to the bank and said, “God, someone stole all my money!” and they were like, “No, that’s the IRS.” Stylists also need to know what type of company they should form: an LLC or an S Corp, for example.

Every graduate from the program gets an interview with the Only Agency, a talent agency that represents stylists, photographers, makeup artists, creative directors, and production designers. But how do freshly minted stylists attract clients?

You have to be proactive. Your social media is your portfolio, so are you posting photos of you and your friends vacationing or are you doing test shoots? Getting representation isn’t the end-all be-all, you’re still a business owner.

Being a stylist has high startup costs. How did you handle that?

A lot of times your success is dependent on your credit score. I used to borrow clothes for Zendaya to wear and then return them. Luckily she was a very responsible 14-year-old. When you’re starting out, if the [fashion] houses aren’t lending you clothes, you have to get clothes one way or another. I would thrift a lot. And even when you get more experience and you’re taking things out on consignment, you’re still financially responsible and you have to make those clothes come back the same way. You might have to pay [off] your Amex in 30 days, but you might not get paid for 60 days.

When did brands start reaching out to work with you?

It took a lot of hustle. When Zendaya and I first started working together, I had the vintage store, so a lot of what she wore came from there. I would only put her in things other people had worn because at that time the weekly [magazines] were really big and they had “Who Wore It Better?” pages. So whoever got the “best dressed” got the most press. I would go into showrooms and only take things other people had worn, and week after week she got featured in the weeklies—99% of the time she would win. Then brands started to pay attention and started to call and the world started to open up a little.

What was it like to work with Zendaya in those days?

Her parents trusted me and let me do anything, including making her wear Louboutins until her feet got blisters. They just trusted the process. Everything was more structured at the time. If you weren’t a singer, you didn’t go to the Grammys. But I would plead with her publicist and say “I’m building something.” So she would just pop up at the Grammys looking incredible. She wore a dress from Ungaro to the Grammys, and the next day Fausto Puglisi, who was creative director of Ungaro at the time, called me and said, “I want to take her to the Met Gala.” That became a huge moment in our careers.

How do you know when a partnership with someone isn’t going to work?

Some people come and they see Zendaya or Céline Dion and they want that instant magic. But sometimes magic takes time. I want to know who I’m working with to be able to dress them authentically. The biggest compliment I ever get from my clients is that none of them look like each other. That takes time. Some people would be upset that they weren’t on every best-dressed list after our first red carpet. Sometimes you have to make a business decision and say that it isn’t going to work.

What led you to announce your retirement on Instagram?

I just hit a brick wall. My career had got so big that there was nowhere for me to go other than do more work. I received all the accolades. I was the West Coast contributing editor for British Vogue. I did 32 magazine covers, and there are only 12 months in a year. I was managing a global team with four assistants in L.A., two in New York, one in London, and one in Paris. I had a family tragedy the year before. I felt like I had this burden of being the face of what styling could look like, being a Black man and all the things that meant. I was tired. At that moment I felt not appreciated. I had been invited to Miami to walk the [Hugo] Boss show. I was in the car with my publicist and I just started crying. I just went and found this generic photo and I posted it with the announcement. [Afterward] my phone was ringing and I just wanted to be left alone. I didn’t know if I wanted to retire, but I just wanted to be left alone, maybe even for just a couple of hours.

Did the reaction to the announcement surprise you?

I didn’t think anybody would care. The story was in the news cycle for a week. We’re still talking about it. Naomi Campbell called me and said, “You are not retiring. We need you! People look up to you!” Edward Enninful [former editor-in-chief of British Vogue] called and said, “You will not give up.” My phone notifications wouldn’t stop. I was like . . . what did I do? And then I felt like I had to stand in it.

You told me in another time that retiring allowed you to be happy. What’s the secret?

I believe happiness is a habit. You have to work on it the same way you work out at the gym. I learned that it is a process. You have to wake up every morning expecting that today is going to be a good day and you’re going to be happy. We can’t control everyone around us but we can control our emotions and the way we react to things. I feel more powerful and more in control of my choices for the first time in a decade.

In the past you’ve said that you kept up a persona or maintained a facade. Do you still do that?

LA. is a very dangerous place. When you start to gain notoriety, people start to treat you in a way that can be very tricky psychologically: You start to think that you are the celebrity or the star. There are a lot of things I did when I was much younger that I didn’t really care to do, like partying and being in a scene and out all the time. I came to L.A. with blinders on and I thought the easiest way for me to not experience peer pressure [was] to do things that make people not like me. Because if you don’t like me, then you won’t invite me, and if you won’t invite me, then I won’t feel bad about not coming. It was easier for me to create this persona where people just didn’t know who I was. It was a way to protect myself. I was like a snake that is not poisonous at all but has all the markings of a poisonous snake.

Do you still keep up a facade?

I don’t need it anymore. I want people to see the authentic me. I want them to see the nurturing, genuine, softer side of me.

We’re in election season. How would you style Kamala Harris?

I don’t know her and I don’t know what her personal style is. She’s 59 years old. She’s fit. I would lean more into that. I think that younger people would enjoy seeing it. I would have liked to see a little bit more of a waist. But I’m known as a risk-taker and a disrupter.

Whose style do you admire?

Prince. I wish I had gained notoriety early enough that he would have noticed me.

Do you always check people’s outfits?

I have this bad habit that I have to fight every day. When I see people, I automatically go, “How can I fix it?”

How would you fix my outfit?

So although you knew that you were going to interview me and I will be sitting next to you . . . you chose to wear . . . Vans. But if you were to wear something else, you would not be comfortable. If [an outfit] makes you feel comfortable, confident, and powerful then you have made the right choice.