Libby Andrew

Libby is wearing a dress by A.L.C. and Veronica Beard shoes. Portrait: Caroline White

FASHION INSIDER LIBBY ANDREW KNOWS THAT SOMETIMES THE BEST WAY TO TELL OUR STORIES IS TO FIRST TRY ON AN IMAGE. USING FASHION AS A PAINTBRUSH, HER NEW CAMP SHOWS KIDS HOW TO TRY ON DIFFERENT HATS AND THEN TELL THE STORY THEY WANT THE WORLD TO HEAR.

Libby is wearing a dress  by A.L.C. and Veronica Beard shoes. Portraits by Caroline White.

It seems the word of the year is “discomfort.” The word has come up in every single article and every single conversation I’ve had in this edition. For example, Marci and I just spoke on a podcast about how we know our craft but neither of us has ever been a business owner. It’s new territory. Someone told us “that’s good because if you’re uncomfortable, you’ll find help to get comfortable. That’s how we get ahead.”

It’s true, it’s true. You know Alexandra Wilkis Wilson, who started Gilt Groupe, wrote a book and one of her big themes of the book is creating a team. And I resisted that for a long time. It wasn’t so much that I didn’t want other people’s expertise, but it was more this idea that I’ve got to do it all myself, and If I don’t know how to do something I can learn how to do it. I was beating that drum for a really long time and then I thought, well, if I can feed out just a little bit, here and there, it would be helpful. It was more than just getting the work done, it was also about allowing a collaboration to happen. Feeding off of other people and their ideas and stories is so helpful and it actually pushed me much further than I would have thought. The creative side which is wonderful and what I love to do and what I’m comfortable with. And then there’s this whole business side that I’ve also learned to love, but you’ve got to have both.

That “jack-of-all-trades, master of none” feeling is not necessarily a bad thing. I’m okay being a jack if I can find a master of the things that I can’t conquer.

It’s funny you say that my dad used that phrase all the time. It’s kind of like a cautionary tale. You want to be like a jack-of-all-trades, master of none, but I think it’s necessary to be able to understand and operate on a lot of different levels when you’re running a business.

This almost seems like the theme you’re teaching the campers—to dip your toes into a little bit of everything, and then learn how to put it all together. Is that what you were going for with the campers?

I’m so glad you said that. Because it kind of goes to the origin story of why I came up with this camp in the first place. When I was growing up my parents were pretty strict, and I came from a very artistic family. It was just always second nature for everybody, so I took it for granted. We were always talking about art. Someone is always playing instruments and everybody could draw—you weren’t special if you could draw because everybody could. My mother and I liked to look through fashion magazines together and critique color, art, style, expression, everything. It was fun. Once I got into my middle school and teenage years, I was veering away from my mom a little bit, but I still loved the fashion world because it was a world of imagination and storytelling. It allowed me to pretend that I could become whatever I wanted to be. I did that through fashion. “I dress like this, I can act like this and I can visit Paris, and I can be a pilot or an astronaut.”

That’s where the idea for the camp came from, with this feeling of “allow yourself to imagine, and then tell your story with that imagination.” I think fashion is one of the best ways to do that. Since I had the experience, I could actually teach them how to create and tell their own story.

What are the basic principles that you’re teaching? Are you starting out pouring over pictures like you did with your mom?

The very first thing that they get to do, so they can see if this is something they actually want to do, is this course where they build their own fashion magazine. The first thing to happen to you is copy an advertisement. It can be a physical magazine or could be online, but I want them to look for the ones that seem to be the most outrageous to them. So they can start thinking about the fact that these impressionable images are very abstract; they don’t always make sense. Sometimes they’re based in reality, sometimes not. So what I’m getting them to do is think: If I copy this advertisement where someone is using a shoe as a telephone, what does that mean? How does that feel? This exercise allows them to break out of their regular way of thinking and encourages them to tell a story—whatever that is. I’m trying to get them, during the course, to discover a sense of self purpose and gain confidence telling their own story.

There’s been a lot in our culture lately about creating strong women leaders. How do you do that? Where does that come from? I really believe there’s a lot of healing that needs to be done, because of the pandemic, and even just in the nature of our country right now, we’re in a very pivotal cultural time, and I think sometimes the kids get lost in that. How do we get them to find their courage and come back from that?

It’s a very good point, and to add to that, sometimes kids get lost because we, as parents, put them in these bubbles because we don’t want them out in this big world where there is war and conflict. But when we do that and they are ready to leave the home, they’re a little more naïve, and maybe they don’t get to see Paris or do any travel and they avoid. I think what you’re doing, besides leadership training and inspiring imagination, is incredible. You’re using a tool—the fashion world and make-believe—which seems almost counterintuitive. But somehow it works.

“Part of this business for me is to put the fun back in fashion. For too long it’s been used as an intimidation factor and I don’t think it needs to be. It never was for me. It was more a way towards self-expression. ”

What I’m doing here in this camp is really about having your own style, developing your own style. And reminding you that you can switch it up. It doesn’t have to be the same thing all the time. And you don’t have to have the fanciest, most luxury item to make a statement. I’m hoping to break apart these ideas about fashion being the haves and have-nots. I’m trying to give an invitation and build a community where girls, wherever they are from—Montana, Australia, Chile—can realize they have something in common. It’s about sharing their ideas with regard to art and regard to fashion instead of feeling like I’ve got to have “this” and I have to dress this way.

It sounds like you’re re-creating a little bit of what you and your mom did when you went through magazines page by page. I’m curious. How did you go from sitting with your mom to Anna Wintour’s office?

It’s funny because I get asked this question a lot. I majored in philosophy at Wheaton College, in ethics, and I did a lot of theater. I was actually planning to go to law school because I have a very big justice component in my life. Justice and creativity. How do you marry those two? But anyway, I had friends who had gone to law school and didn’t like it, so I thought I should try something else and then get back to that later.

I moved to Manhattan one week after I graduated college, and I worked for Guess Clothing Company, doing their special events. It was so fun. We went to Macy’s Herald Square, Kate Moss was one of the models once, I got to pick the music and the themes. It was super fun. But I learned a big lesson there. They hired a new president and cut the special events department. At the time I was devastated because I felt like I had put in blood, sweat, and tears at that company. But in hindsight, it was great because I stayed in Manhattan.

I love that city. I loved the cultural diversity and just that pulse there that makes you feel like you can come and do anything you want. But I stayed and became a temp at Anna Wintour’s office. She had let go of a couple of different assistants and I was working for the public relations director, who thought I should interview with Anna Wintour. I was a little bit nervous, but I love meeting people and I thought, why not? If I’m going to get offered the interview, I’ve got to go. So I sat down with her and we actually got along very well. We just clicked. You know why? She is fascinating. Her office is fascinating. The photographs she has, the flowers, the whole thing. I remember feeling like, regardless of what happens here, this is going to be an incredible experience. I could answer all her questions about fashion because, without knowing it, I had it memorized. So that’s how I ended up there. It was really not about connections, it was just good timing. What’s that saying about opportunity meeting hard work?

So now you’re absorbed in the world of fashion and you’re picking up all sorts of knowledge about the industry, about running a publication, about the components that go into this.

Yes! You know, the thing I want to say about that is the best thing about being her assistant is that it was more of an apprenticeship because as reserved as she is, she brings you into every area of her life. You go to her house, you read all the copy that comes across the desk. One year we put Hillary Clinton on the cover. And Oprah Winfrey. So I was dealing with Hillary Clinton’s office and the White House and all of Anna Wintour’s friends, Oscar de la Renta, Karl Lagerfeld.

All these different people you’re speaking to all the time. She wants to be able to leave that office and go off to the fashion shows a couple times a year and not worry at all that her office is being run well. And so, her assistants do that for her. So yeah, so that’s kind of what it was like to be in that office.

It sounds like you were in the middle of the best social studies class!

It was like that.

I never would have thought that fashion could open up my world to politics, to philosophy, to social activism—because you just named all those things in every person that you spoke of.

Yes! Henry Kissinger would even call the office, you’d be surprised. You think This is just a fashion magazine. But this magazine brings together so many different industries. You’ve got the journalists, and the journalists are some of the best in the world—Joan Didion and Dodie Kazanjian—and they’ve all got their whole world of people. As far as designers go, I mean, it’s walking, living art and they dress those people with their clothes. You’re telling a story. Think about that. If a woman wants to feel powerful? Some people probably wouldn’t care how they look, but some people care about what they’re wearing and how they present themselves.

How does this philosophy work into what you’re teaching your campers?

I think it’s a matter of helping them develop this idea that every person has a story to tell, and every person’s story is important. Each girl that comes into my camp will believe that they are important. I want them to get that feeling from taking this course. You have a story to tell, you have original ideas. It doesn’t matter how old you are, let’s help develop that confidence in being able to tell your story.

Something that I am going to be very cognizant of is focusing on the positive aspects of each person’s story. When we get together in our weekly Zoom, or if we communicate at all, one of the rules to be very strict about is positive feedback only. Because you’re going to see what does work, and automatically girls are going to say look at all of the things that don’t work, and that’s too easy—it’s too easy for those girls to worry about that. So I want to start digging into what does work. What did I share that people thought was cool? How can I start to make my mindset one of forward thinking? It doesn’t mean don’t tell your story. Yes, share your story, but try to get there with positive love.

And empathy and solidarity. That this is a tool to open up the world to you if you let it. That sounds like what you experienced in Manhattan. You found a way to open the world up to you with a nontraditional tool like fashion and publishing.

Absolutely, absolutely. One of my favorite quotes from Eckhart Tolle is “You create more of what you focus on.” That’s one of my mainstay principles. Every time I feel myself getting negative or fearful or have some anxiety, I replay that in my mind. How can I think positive thoughts instead of negative ones? How can I take a different path that puts me in a good direction? For me, looking at fashion, because it’s colorful and vibrant and imaginative, is one way to do that.

I am interested in knowing more about your philosophy studies because I think that really everything you do is very thoughtful and inspired. First, how did you get to kids who might think the only thing about fashion is what they see on Instagram?

Thank you for saying that about philosophy. What a fantastic question because I don’t know if I would’ve thought to say this unless you asked me: I believe there are human universalities. You might look at Facebook and phones and all the power of technology in your hand and believe it gets a lot of people into trouble—I understand it causes a lot of competition and self judgment and all these things—but if I dig down a little bit deeper, I also think that it’s a way to relate to each other. There’s this curiosity factor. So my belief is, with this camp and with the technology that we have—because I don’t think it’s going anywhere—I would like to have kids use their technology and not have it use them. Because every time you get on your phone, every time you look at something on the computer, you make a choice. I would like to empower them to know how to make choices. How to decide what they’re going to do with their time. How much time they want to stand looking at something and learning from their phone. How much time they want to just let off some steam and look at TikTok. And then how much time they want to put all of it away and go do something. When you do fashion, it’s very physical because it’s a garment and it forces you to use your hands. To lay something out, try something on your body, look in the mirror. Shop with your friends, share ideas. So, it’s not so much that there’s evil in fashion or evil in a phone, it’s how you are using them.

Back to your question of the philosophy, I think those philosophies come from my feeling that all people everywhere, it’s why this Ukrainian war is so painful to watch and look at because on a universal level moms know what it’s like to have children, what it’s like to protect her children, what it’s like to make sure that they’re eating properly, and they’re over there in Ukraine stuck in a situation where all that is out the window.

And, you know, it’s just horrific obviously. And so my feeling is, yes, it’s interesting.

“How do I come from the fashion industry and yet talk about all these things? It’s because life is very rich and complicated and it involves all these different aspects from what we wear, to what we watch, to how we use technology.”

Wow, that was a mouthful!

It was so well said! My daughter and I were talking about when I was a kid, or as she calls it “the olden days” …

Right. The ’90s.

Right! Ha! To your point, I don’t want to blame technology, but we were using our imagination a lot differently then. We tried things out, we sought people out. But now—and my point in this is to tie technology and fashion together—we can learn about how jewelry in one culture was used to show stature, and how tattoos and makeup represent wealth and power in another. Beauty, women, fashion—all are so different in other parts of the world, and this new technology can teach me about different cultures in a way we couldn’t “in the olden days.”

That’s a brilliant point. In fact, part of my website I’m developing, is interviewing designers from all over the world. And not just big designers we all know, but there are women across the world doing incredible things and helping communities. They make this beautiful fabric in Africa and then it is sold to manufacturers who then make it into clothes. And it provides income to those communities in Africa that need it.

These designers have gone there and discovered the most beautiful fabrics in the world. And people here find something unique and different and special and something with a story. So it’s bringing those women in Africa together with women here. There’s a way for us to come together, and that’s the benefit of technology.

But as we use the technology, we also don’t want to lose the wonder of the everyday fun of going outside our house and playing. Or lose the basic connection with other people, and I think that’s the biggest fear right now. We all know that instinctively there’s so much value in meeting each other face-to-face as opposed to via technology.

You and I often go down rabbit holes which is my favorite thing about our conversations!

I hope so!

The idea that these girls are going to be meeting each other through your camp, from all over the world, and learning about the different corners of the world. It’s going to change a lot of the stories that they’ve heard.

Actually, I had written a book a while back and was shocked when this girl from Pakistan got in touch with me to ask about the next book. It made me look at the demographics from the book sales and I found someone in Libya and someone in Japan and someone from Canada, and it’s exciting to me because that’s part of the thing that made me think of this camp. I realize the camp is a way for people to understand how similar they are. Yes, we can have a lot of differences, but the human nature part of it is that we all want to get dressed and develop a sense of purpose, and fashion is part of that, and there are a lot of people who are interested in fashion and telling their stories. And there are a lot of people who can relate to each other even though they’re from across the world.

These girls are going to be learning new things about what happens outside of their own homes. Now maybe when they go out in the world and they see conflict like they do in the Ukraine, they might be more empathetic.

I think part of the human condition is to pre-judge other people. To safeguard your expectations of what’s going to happen, right? But what’s wonderful is connecting on some basic level and then discovering there’s a lot more similarities than you would’ve imagined, just being people in the world having a human experience. I’m hoping that will also be part of their experience in the camp. If nothing else, it will start to infuse the types of discussions we have, and it will start to make them wonder if it is valuable to have any pre-judgments? You never really know someone’s story until you talk to them.

I think of the icons, both real and in fiction that use fashion to influence. Jackie O, you know, what a wonderful woman, what an advocate and philanthropist. The one thing that everybody knows about Jackie is what she wore.

I had her book standing right over there. Yeah, she was a fashion icon.

Yes! And Princess Diana. Talk about an advocate! We all know her life’s work, but if you don’t you still know how she wore her hair and what dress she wore. So many of us are attracted to their look but then are influenced by what they cared about. I guess you’ve got to use the tools that you have to attract the attention to the causes, the stories that you want to tell.

You know who I’ve been noticing lately, right there front and center, Jen Psaki and Nancy Pelosi. I wonder how much thought they put into their wardrobe and if they’re purposely wearing certain colors on certain days. I think we’d be in denial to think that we’re not attracted to some people, that we’re not interested in them because of what they’re wearing. Sometimes we really are. How many people tuned in to watch Harry and Megan get married? They want to see what she’s wearing. I don’t think there’s anything wrong with that! I think it’s fine—yeah, yeah I think it’s fun. And it says if I want to present in a certain way, do I want to wear something clean? Or I don’t want to present that way. Maybe here I want to present in a way that’s more subtle, or makes people keep their distance, or whatever it is, but allow yourself to discover it. Try on each thing because if you don’t try different things, you can never find what is comfortable for you.

I think that is the life philosophy here! I mean, look at you. You tried on the author outfit. You’ve tried on the major media giant that is Vogue magazine outfit. You tried major label clothing retailer outfit…

I went to Imagine Entertainment and worked for Ron Howard and Brian Grazer. Yeah, I did. I had to try a lot of different things before I settled on “entrepreneur.”

I’m still gonna be discovering and I think giving myself permission to shift when it’s not right and giving myself permission to make mistakes. Why is it such a big deal to change? You’re eventually going to find a fit. I have to tell you, one of the best things about the job I’m currently doing is, when I’m working—and I have four kids, so I have only a little bit of time that I can devote to this—but when I’m working and I find that flow, I absolutely love my work. That’s what keeps me coming back. That feeling, that moment when I absolutely love all the different aspects of this work.

You’re showing that fashion can be about expressing your story. It’s just another paintbrush.

Yes, it’s another paintbrush. And to start the camp off, I’m encouraging them to use the clothes from their own closet. They can collaborate or they can do it all completely on their own. I want them to use all their own clothes, and I want them to pretend the clothes in their closet are the clothes from the season. I give them examples of times when that can easily be true—from some of the top designers—when they had a year of doing T-shirt and jeans, for example.

You have to be yourself. Sometimes it takes courage to be yourself. And you could be confident being yourself, but you have to be able to exercise those emotional muscles. Sometimes you don’t get a lot of opportunities to do that.

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