Kelly Gray was the heart and soul of St. John for decades — designing the collections, running the business, and creative directing and modeling in the brand’s iconic ads. Then, in 2005, when the brand was at its height, the company came under new management and Gray and her family were pushed out. Now, 13 years later, Gray is finally ready to spill the tea about everything that went down before, during, and after that tumultuous time.
Let’s have a kiki.
When did you first start modeling for your mom’s brand, St. John?
I was 15, and my parents were looking to move the photoshoots from New York to California. They needed a body to test the photographer, and then the pictures ended up in Town & Country. My first shoot!
The St. John ads in the late ‘90s were so unusual and intriguing. What was the concept?
The ads were meant to be provocative. Our line was absolutely not. We were conservative, and we dressed lawyers and politician’s wives, but that isn’t very aspirational or fun to look at. So we created this fantasy; the idea was, if you wore St. John, you could be like me and have five men following you around the world.
How involved were you in producing these shoots?
Neil Kirk and I worked together; he was our photographer for probably 15 years or more. One of my last shoots, I got to work with Peter Lindbergh, and that was a real treat. But Neil was my creator and I was his muse. We would start with locations. I was chief merchant and creative director for the company, so I’d be midway through developing a collection, and we would start to think about where we were going to shoot. Then, I’d go back to designing, and we’d start sculpting the collection to make sure we had great clothing to photograph in these magnificent locations.
How much were you spending on these shoots?
Surprisingly, not very much. We used a lot of airline points. We weren’t known to be great payers, but everyone wanted to be on a St. John shoot. Neil and I would just pick a location, get there a day early to scout, and hope for the best.
Tell us about the male models. You were always surrounded by men in those ads.
Neil never liked for me to get too close or to talk to them. He always wanted to use them positionally and didn’t want a lot of interaction. On one shoot, I actually ended up dating one of the models. I remember seeing him on that first day and saying to Neil, “I don’t like him. You keep him away from me.” Sure enough, by the next day, I couldn’t stay away from him. We dated for about six months, but that was the first, last, and only time.
You worked with a lot of exotic animals, too. There was that enormous white tiger…
Oh God, yes! That shoot took place in Nevada, where literally everything is legal—even things that shouldn’t be— and the trainers were very unusual, just really, really odd. There’s a famous photo of me in a white dress holding a tiger by a chain. I asked Neil, “Can we get somebody else to hold this stupid chain, and just Photoshop it?” He said, “Oh, darling. There are some things that simply cannot be Photoshopped!” So he made me hold the tiger’s chain, and the tiger was really like this giant, playful kitten; it was swatting at my legs. I only lasted maybe six frames. I said, “Neil, I have never said this to you in my life, but I need to step off set.” I went into the trailer and threw a giant shot of tequila down my throat. My hands were shaking. I look around the corner, and the tiger was loose, chasing an assistant, who was throwing tables at the tiger. Tigers are really scary! I’ve held a lion’s head in my arm and it was fine, but panthers and tigers are scary.
Did you ever model for any brands besides St. John?
When I was 17 I signed with CESD. I wasn’t super tall or super skinny, but I photographed beautifully, so they sent me to Chicago to do catalog work. I worked very steadily, but then my dad would see me in these newspaper ads for sales at Macy’s, and he really didn’t like it. He wanted to own my ass! Basically, he wanted me to be exclusive with St. John. Then, when I became CEO, I wanted to resign and hang up my pumps, but Neil went to my dad and said, “You can’t let her do it. You have no idea how these ads work and how the clients follow her. I want you to add her name to the ad. I want to make her famous, so people will connect with her.”
Did you get recognized on the streets?
Yes, I did. I knew I had made it when I had my own stalker. It was scary and exciting at the same time. It was my moment of fame, and the moment lasted quite a long time. Never to the point where fear ever inhibited my life, but people would recognize me: “Aren’t you the St. John girl?”
You had a very distinctive look, particularly your hair.
I’ve probably have had fewer than eight people cut my hair in my life. Once you’ve had Sam McKnight cut your hair, it’s very difficult to let anyone else near it. The platinum blonde was high-maintenance, but people just loved it.
How did you go from modeling in campaigns as a teen to becoming company president in 1996?
I actually started at age 12, at the reception desk. I just was working all my life, and then I went off to college, and I was floundering miserably–partying and gaining the Freshman 15–and I called my dad and said, “This really isn’t for me.” So I went back to work and they gave me collages to make. If you ever want to make someone feel useless, have them make a collage and tell them that’s their day. I decided to put together an ad budget. We were shooting in California, and I thought we should be shooting in New York. The California photographers were really slow. They couldn’t pump out a bunch of shots per day, and I had put this book together—Arthur Elgort, Neil Kirk, Peter Lindbergh, Francesco Scavullo—and the company funded my shoot! They said, “Okay, go to New York.” We had three days. We traveled with super saver tickets — me and one other girl lugging the clothes around in 25 suitcases. We got to New York and, sadly, one of the photographers we booked had a heart attack and nobody called us, so we got out my black book and started cold-calling people. Somebody volunteered to shoot at night, even though they were booked. We came back with beautiful photographs, and on budget. That’s how I got my start in advertising. When we started advertising, we had one page every other month in Town & Country and when I left [the company in 2005], we were doing over 200 pages in the US.
Those ads were everywhere. In 2000, it felt like there were six pages of St. John ads in every issue of W or Vogue. How much were you spending on those placements?
Probably about $10 million [per year]. It wasn’t as much as you would think. We grandfathered in some really good deals. I was probably one of the best negotiators in the business. George once brought me in to talk with John Kennedy Jr. to tell him what to do with his [magazine]. That was a moment of pride for me. Publishers really respected me. I didn’t work very much with the editors. Everything I built, I built with the publishers. The spend on the shoots with 0.5% of the total advertising budget; today, they’re hiring actresses, celebrities, and supermodels, so you tend to spend millions on shoots and then there’s not much left to advertise. We were the opposite.
Angelina Jolie started starring in St. John ads in 2005, and she was rumored to be making $10 million a year.
David Lipman came on board and brought on a new CEO. I did a shoot with Peter Lindbergh, and David let me know it was my last shoot. It was a little sad; I don’t think I was quite ready for it, but I didn’t want to hold the company back. Then we started conversations Angie—and this was before Brad [Pitt]—and I left right in the middle of the process. I’ll be honest with you, once the whole scandal erupted [with Jolie, Pitt, and Jennifer Aniston], I would’ve probably not gone forward with the contract. Their expectation of her was to be a brand representative, not just be photographed. They actually brought me back to try to get some photographs of her—not just of her face, but of her actually wearing the clothes—and somebody had to help something she would be comfortable being photographed in.
You couldn’t actually see any of the clothes in those ads.
I think they led her to believe the company was going to be radically different design-wise when they were courting her. I just remember when they brought me back to work with her, the goal was just to get more photographs. Ultimately, we got the photographs. And then, we didn’t have enough money to place them.
Your parents founded St. John in 1962; in 1990, they sold 80% of the company to Escada. What’s the story there?
I’ve never shared this. My dad sold to Escada because he had health problems, and my brother and I weren’t ready to take over the company. He wanted to make sure it survived. At that point, I think we had 2,000 employees; then, Escada owned us and I trained under Wolfgang Ley. He taught me about international marketing and had me flying all over the world. Then Escada came into a little bit of a rough patch and we didn’t want to be sold off to the highest bidder, because we were a cash cow at that time. So we took ourselves public and still retained our 20%, but the Escada shares became common shares. The day I was named president [in 1996], the stock dropped 20 points. Nepotism at its finest, they said.
What happened next?
I went from San Diego to Boston, meeting with every financial analyst telling my story over and over again: that I wasn’t an idiot, and that this was a great move for the company. The stock rose and split, rose and split. Those were the years we went from $100 million to $400 million. Then, we were approached by a venture capitalist company to take ourselves private. They saw potential; if we were doing half a billion, they thought they could help us get to a billion. But what most venture capitalists want when they buy a family-run business is to replace the family. I found that, in hindsight, to be very true. When they brought in the CEO, he and I did not get along. The whole thing unraveled in about a three-month period; I left, and my mom left with me. I think they were almost happy to see us go at that point. We represented the past. It felt like the right time.
But two years later, in 2007, St. John asked you to help them, right?
It was well over a year. The involvement was intense and initially we saw really good results in the numbers, but we grew apart. You can’t have two people driving one car.
Was there any discussion of you appearing in ads again?
No. If it was my company, I would have. I think it would have sparked some loyalty from older clients that remembered those days, and loved to be taken on those journeys. People always asked me where we were going next. Would there be more baby animals? We always had this sense of anticipation and excitement.
Tell us about your life after St. John.
Most everybody knows I became friends with Tommy Lee. Yes, just friends. [Motley Crue’s] Nikki Six and I went into business together: We started a rock and roll [fashion] company, Royal Underground. Everybody used to call me an executive rockstar. I had no idea how much I had in common with a rockstar until I actually met them. It was a fun world to visit for a couple years, but I don’t think I could live there. I got to expand creatively, do things in my life I never dreamed of doing. Going to the White House for me was no big deal. Getting on a tour bus, oh my God! Meeting Steven Tyler: that did it for me. We had distribution with Neiman Marcus, Bloomingdales, and Nordstrom. But it was very elusive look. Not everybody wants to look like a rockstar; you kind of just get these beefcake guys wanting to wear the clothes. It wasn’t the business I thought it would be. Really glam rock I understand, but when it gets ugly or strange, it’s not in my DNA to be passionate about that.
You work with you
My mom came to the office and our creativity together was still off the charts, so we started Grayse. It’s a lot of eveningwear, skinny pants, leggings. I kind of followed the whole Lululemon craze, but their leggings are $120, and ours are $1290. I like embellishments. I’m like my ads—glamorous, sexy. We love that people come to us for important occasions: weddings, bar mitzvahs.
Would you get back in front of the camera now, for Grayse?
I never really loved being photographed. I had panic attacks. You can ask any of my hairdressers or makeup artists. I was always dying and today, I know they were panic attacks, but back then, I just thought I was sweaty. It was embarrassing and it was tough. It used to take me at least 30 frames to get magic. Every once in a while, I could get to it faster, but by nature, I’m a little bit more shy — camera shy for sure. So you don’t put yourself in front of the camera for Grayse? At Grayse, I put three women in the shot and I try to embrace modern marketing. These girls are real, they’re beautiful, one of them, I’ll be honest with you, is a dental hygenist. I put them in groups of three because your younger millennials, you don’t know what’s going to catch their eye. There’s still this kind of mystery about what they love. A lot of people stop just because they notice that all the women aren’t the same age, size, or color. That’s all by design. I don’t think I could build this company around me. Philosophically, that worked for St. John, where I think what works for Grayse is the more modern kind of glamour. Trying to appeal to lots of different people. The definition of beauty definitely changed a lot in the last 10 years, and especially with the younger generation. If it’s too glamorous or too standoffish, they’re not really interested.
Who is the Grayse customer?
These women are in their 40s, but their bodies are better than most 20-year-olds—and they have money! They want to look special. We tried to be less expensive, but it’s just not in us. We don’t understand that market. We understand glam. Lots of money. We’re great at creating luxurious, detailed, embellished, amazing pieces that are remarkable, memorable, one of a kind. That’s about the only thing you can offer people these days, because we all have 20 pairs of black pants. You need something special.
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