Madewell’s New CEO Talks Jeans, Healthy Conflicts, & The Privilege Of Failing

In the past few years, Libby Wadle has made it her job to know everything there is to know about jeans. What makes good jeans good? What makes them last? What makes jeans a better bet than, gulp…leggings? In her quest for denim omniscience, she’s come across one gripe that’s made her job particularly difficult: The Sisterhood of the Traveling Pants.
“We have probably one jean that fit nearly every body. They’re almost a traveling pant,” Wadle tells me one sunny morning from her corner office at fashion retailer Madewell in Long Island City. “You can sleep in them, they’re so comfortable. But it fits all kinds of shapes and sizes because of the stretch. They’re made with Tencel. But...those? Especially those?...” She shakes her head. “They don’t stretch!”
The idea that there’s one pair of jeans that will magically fit America Ferrera, Blake Lively, you, and me is ludicrous to Wadle, as it is to any grown woman who’s ever tried on a pair of jeans. This one-size-fits-all scam also, appropriately, applies to retail where the idea that one cookie-cutter approach could save any brand is pure fantasy. The fact that Wadle is allergic to that mindset is a good thing. After all, Madewell — the J.Crew Group-owned company of which Wadle was recently named CEO — needs a fresh approach to succeed. The two brands that Wadle previously held positions at, J.Crew and Gap, both experienced stunning rises followed by crushing implosion. In fact, it’s been rumored that one of the reasons that Wadle was promoted from brand president to CEO was to prime Madewell for an imminent IPO in order to pay down part of J.Crew’s $1.7 billion debt.
When asked about the potential for an IPO, Wadle hedges: “The stakes are higher now. We have pretty aggressive growth targets. The job becomes a little bit more complex. Today, we're focused on building a billion-dollar brand and delivering the growth for Madewell. That's what I'm focused on.”
One thing that makes this Madewell era different is that Wadle’s longtime mentor, Mickey Drexler (the former CEO of J.Crew Group and Gap Inc.), is no longer by her side. Credited with turning Gap and J.Crew into star retailers, Drexler was the head of Gap in San Francisco, where Wadle first worked, and later convinced her to join the newly reinvigorated J.Crew in 2004. It was Drexler who first purchased the rights to the Madewell brand in 2003, branding it as J.Crew’s “little sister” brand, and appointing Wadle as its brand president.
“There have been many growing pains. There’s been a lot of stumbling to find out who we are,” Wadle tells me. “But now our challenge is to really protect the brand as we grow and do the right thing for the brand without being too precious.”
Wadle sat down with Refinery29 to talk about what she’s learned in her two decades in retail, and what past stumbles have taught her about Madewell’s chances at becoming a billion-dollar brand.
Refinery29: You’ve been selling clothes for your entire professional life. Why?
Libby Wadle: I used to work at those kiosks in the mall — you know, the ones in the center? I was 14 when I worked at one of those selling children's clothes, because I wasn’t old enough to work in a real store.
I went to college to study English, which I'm super happy that I studied what I wanted to study. But what I really loved was my job. I worked part-time to feed my shopping habit. Back then, retail was pretty simple. It was just about having great clients come back, and I fell in love with that. When I graduated, I decided to take a big risk, and move to a city I'd never been to before. In San Francisco, I continued to work in retail, and had a fortuitous meeting with someone I helped at the store who connected me with a new training program they were starting in merchandising. Back in the day, there were a lot of big department store training programs in New York, but there was not much anywhere else. It felt like I had hit the jackpot. It was my dream job. To this day, it's still a high for me.
In those days, merchandising was very straightforward. There wasn't a lot of extra intelligence you could rely on to make decisions. It was thrilling to pick the right thing and have a best seller.
To this day, I still love coming in on a Monday and sitting with the team to go through business and hearing what's selling. They’ll always laugh because I'll be having a chaotic week, and I'll come back here and do a review, and I'm like, 'Whew — I'm so glad I'm in this meeting right now.' I just feel very at home doing what I love to do.
You work at companies for long stretches at a time. That longevity and loyalty to one company isn’t common these days. Can you sell me on this idea?
I worked at Gap for around 10 years. I've been at J.Crew and Madewell for 14 years. It works when you're at a company where you can find the opportunity to reinvent yourself. It works at a larger company that has different types of opportunities, with leadership that has an entrepreneurial drive and is open to new things. If you land in those companies, and you raise your hand when you hear a conversation happening, and you take it on whether it's part of your job or not — if you're always opting in, that's how you can thrive and continue to reinvent your experience.
When I took the job at J. Crew, it was for a job I actually had no experience in, but I was like 'alright. I want to work for you [Mickey Drexler]. I knew I was getting in at a time when there was an engaged community around a brand. It ended up being one of the most fun experiences I've had. I was really able to build something out of nothing. I took an opportunity where I wasn't sure if it was exactly right for me, but it allowed me to round out my experience. I think that's the thing: You should opt in for those things that feel scary, that give you that pit-in-your-stomach feeling. If you’re saying ‘I don't know if I can do this,’ you should probably take it. But if you do it, you should not look back or second guess. Because if you do that, you're never going to be successful.
As someone who’s been able to secure a series of quick and big promotions throughout your career, what’s your advice on women who want to advance in their roles?
Promotions are not necessarily going to fall into your lap, but I think that if you position yourself in the right conversations, and you're available and always up for trying — whether you're on the hook for it or not — people appreciate a willingness to jump in with no strings attached. There was a lot of that for me. Jump into things, and be available for things. You don't want to be the person who's always asking for the next job. That doesn't come off well.
I think the mentor piece is important. I had good mentors and partners, and made good connections and relationships within the company. I think that the longer you stay and the better the relationships become, you get a lot of respect and trust, and you're given opportunities because of that. Peer mentoring is great.
I never had an external mentor. It really worked for me to build on the good relationships I had within the company and ask for advice. You get allies throughout. I would like to say that it shouldn't be that hard, but company cultures that are different. I've been fortunate that I've been a part of a culture that's been collaborative in spirit, in a good way — sometimes it can be not so good, if it's too consensus-driven.
I'm sitting here today, and I would love for someone to call and ask 'Can you be my mentor?' You shouldn't be afraid to ask! Most people just don't ask. It's important for women to ask, and not be intimidated.
I’ve always found merchants fascinating, because your job is predicated on healthy conflicts between creativity and business. Do you have any tips for engaging in confrontation?
Merchants need to be skilled at navigating difficult, tense conversations. I think that the most important thing for any of us to do is to listen. If someone feels that they're heard, and you understand where they're coming from, that is half the battle. So many people get caught up in just waiting for someone to stop talking in order to say what they themselves think. The listening part is absolutely key.
Also, do it in the beginning in the process. It's so much easier to get the outcome you need if you work with the person earlier in the process. Therefore, their process is not disrupted. You have to appreciate a creative's process. If you come in too late in the process, it's really frustrating.
We've done a lot here at Madewell to make sure the organization is synched up early so we're kicking things off together, so it's okay to have these conversations, and they don't feel so tense because there's not much work that's already been done. Nothing is worse than developing something, and then hearing when you're about to press go, 'Oh actually...' That goes for everything — marketing, creative, merchandising, design.
What’s been a career high for you?
My brother is a driver for UPS in Alaska. He sent me a picture of a Madewell bag from his deliveries, and he's like 'I've been seeing so many of these! You must be so proud!' I just love those moments where I feel like it's working, it's catching, that's a high for me. Every time I'm outside of NY and someone finds out where I work, and they say how much they love Madewell. I have to tell you, it's amazing.
As for my promotion and CEO title, that's been a high for me personally, but because of the recognition for everything we've built. Recognition for who we are, how far we've come, and that we're deserving of a CEO role because we're an amazing standalone business that has big growth plans. For those of us who've been around for a long time building it — most of us have been around a long time! — that day and that moment was great validation.
Madewell has taken on a few identities throughout its history. How do you connect the dots between what it is now — a denim brand — and what it’s been, which, at times, have included an adrogynous workwear brand, J.Crew’s “little sister brand,” and a faux-heritage brand that got called out by Buzzfeed?
We're not precious about having to pivot to survive and be relevant. When we put a stake in the ground around being premium denim at a non premium price, we let go of some of those other things. That was risky. I look back now and think 'Well that wasn't much of a risk,' because we weren't that big at the time. But it felt risky. We had stores. We had a team. We were going out on a limb at a time when five or six years ago, that wasn't necessarily where the trending category was. We weren’t athleisure. But we took advantage of that knowledge — the technology piece, the fit, the fact that people want to be comfortable but look great — and ran with it.
I think that we get pigeonholed as a young brand, but we're pretty ageless. The ‘little sister’ thing is the biggest misconception. We stand on our own.
Did you have data that gave you confidence that betting on denim would work?
There may have been things that said it wasn't the right time — why would you build denim now when everyone's building athleisure? I have to be frank. I'm glad I didn't pay too much attention to what the market was saying. Sometimes when you can look at the market data — and I know it today, and I know what we created [in spite of that] — you can overthink things. We looked at the financial opportunity, but we luckily did not look too hard at it.
So, why are jeans a smart business move, when there are so many heritage brands, fast-fashion brands, and premium labels who are already doing it well?
Jeans are at the foundation of most people's wardrobes. There's this very sticky relationship that happens when you find a great pair of jeans that fit well because you walk out in them, and people comment on them. Everyone likes to hear that their jeans look great. That I think is what's different and nuanced. It creates this great conversation. That's a great jean, where did you get it?
Today it is the basis of our business. We're a denim brand, and we're about everything you can wear with jeans.
We have so many pieces we sell that can be everlasting in your closet. That's pretty important to a lot of people right now. A pair of jeans you always fall in love with and never stop wearing. An amazing washed leather motorcycle jacket that we've had since the beginning of time, and it's still my number-one favorite item. It goes over everything. An amazing heather-gray T-shirt. There are things we build our assortment around that are just foundational, and they never stop giving to your outfit.
We’re distinguished from other brands because of our quality at our price. We stand behind the technology we use, and that is our differentiator. The expectations around quality and value may fall, and we will be in front of that, but we will never lose site of that's what we're going after. Great quality at a great price.
What’s the community saying?
Well, fit is always number one.
We really want to sell jeans to lots of different types of people, and want to engage with different types of people and hear from them. Our mission is to be as inclusive as possible, and to grow our community. Our mantra is act big, and think small. What it means is we still behave like shopkeepers. We still look for little opportunities to make sure we can amplify single voices in ways that make sense for the community. Listening to someone who writes about a certain fit that doesn't work for her, and what she's looking for. If there's a hometown hero who's doing really well out of Nashville, it’s us giving her a bigger, broader platform on the Madewell site. Broadening the community is the way that you win versus limiting who you want to include.
We're dying for information. We love feedback. It's really, really important. We have so many great ways of getting feedback now, from our reviews on site to our social media channels. We have this really great Madewell group chat we do with our volunteers. There's many different ways to get that feedback. It's very important.
Having experienced that stumble at J.Crew, does that affect your feelings about your responsibilities to Madewell, your staff, and the customers?
That nervous energy is what keeps me going. I feel it when things are really good and when things are tough. Success doesn't define me. I actually think that the obstacles that I’ve been through define me. The things that I've taken away from each of those is what I've tried to put in my leadership experiences here. This high-growth plan is daunting, but I stay grounded in what our customer is saying and what she wants. It's nerve-wracking, sure. I don't want to go through it all again. But I have that experience. And a lot of people don't have that experience. I was lucky to have the super high and, to be frank, lucky to have had the other. Because, I'm here.
The interview has been edited and condensed.The interview has been edited and condensed.
An earlier version of this article misidentified Mickey Drexler as the person who first poached Wadle to Gap. Refinery29 regrets the error.

More from Work & Money

R29 Original Series