Alexander Wang on His 10-Year Anniversary, Clubbing With Madonna & Why He Thinks Caitlyn Jenner Is the Next Oprah

It’s hard to believe that it’s been 10 years since Alexander Wang first entered the collective fashion consciousness. The San Francisco native essentially grew up in the industry, starting his eponymous line at the tender age of 21 with a few knit sweaters — which he intended to be a side project while he attended Parsons School of Design in New York — that became a full ready-to-wear line after two short years. In 2007, the era when socialites were becoming celebrities just for showing up for parties and trolling red carpets, Wang’s clothes were decidedly less polished, and that was a good thing. Slouchy, tattered, yet still sexy, they quickly attracted the denizens of downtown, and he essentially invented the “off-duty model” look. Of course the raging parties didn’t hurt either — Wang enlisted gangsta rappers and rock ‘n’ roll gods like Foxy Brown and Courtney Love to play his fetes, which made him catnip to celebrities who wanted to be part of his merry band of cool kids. “I knew that we were homies the moment I met him and his other friends,” one of his celeb besties, Zoe Kravitz, tells Yahoo Style. “He reminded me of all my friends from high school, not someone in the fashion world. Real. Funny. Loving.”

Though he’s grown up somewhat in the public eye, the essence of Wang’s brand never diluted. His signature line — which now reportedly pulls in an estimated $100 million a year — has evolved to include menswear, accessories, denim, and an auxiliary T-shirt line. Having been called the “most successful designer of his generation” by “The New York Times,” he also took the helm at Balenciaga and last year created a capsule collection for H&M that sold out immediately. While his success has not been without its tribulations — his Balenciaga run will end this season, and there was a labor lawsuit filed by two former employees that was quietly settled out of court in 2012 — Wang has for the most part followed his instincts, and that has fared him well.

At lunch in late August, he is prepping for his fall show as well as the 10th anniversary bash, which he assures will be another “extravaganza” to remember. To herald the anniversary, Wang brought back 10 archival pieces that were voted on via his website and Instagram, and he’s also designed two T-shirts and a hooded sweatshirt that will benefit DoSomething.org, a charity comprised of 4 million people dedicated to creating social change through volunteering and whose mantra is to “make the world suck less.” Fitting then, that Wang enlisted 38 of his famous pals, from Kate Moss to Kim Kardashian, to sit for Steven Klein in the charitable garments. You can check them out here as well as head to the designer’s website.

Yahoo Style: You were so young, 21, when you started. A lot of 21-year-olds would just be thinking: “What am I going to drink tonight?” But you had the weight of a business on your shoulders.

Alexander Wang: Well I would definitely think about those things, too. [ Laughs] Maybe it’s part of my family because my mom is very business minded, so maybe I inherited from her, but I never took it on as a cumbersome aspect. I guess also in the beginning it was just me and my sister-in-law, so there was no one else to do it. And it wasn’t like I had family members who were like mentors or people that I could immediately go to to ask, “How can we do this?”

In the very beginning it was just like, OK, we’re going to figure it out. And we literally didn’t know what a line sheet was, we took our samples in a roll-y case and went from store to store. [ Laughs] That was all we knew how to do. So it was a lot of trial and error, and I think that was the best school because you just learn firsthand how to deal with obstacles and with rejection and also with, OK, that didn’t work, how can we move on and find the next thing.

What were some of those initial reactions when you and your sister-in-law were going from store to store?

Uh… laughter in our face. [ Laughs] A lot of laughing, a lot of, “Ohhhh, so who are you? And, oh you want to see that person? Uh-huh.” A lot of lying, like, “Oh the buyer is not here.” And then someone would come out and it would be the buyer.

Do you think that having your family work with you was instrumental in your success?

For sure. I think more so in the fact that they really just trusted me and supported me in what I wanted, what I felt was right, and what I wanted to do. Allowing me to leave school, of course that was a very big step for me.

Was that a big conversation?

I want to say it was, but when I told my mom, she wasn’t shocked. She was like OK, so that’s what you want to do? She did ask a lot of questions, but she trusted me with what I had planned. And I did it. Plus my sister-in-law was in between jobs, so she said, I’ll just help you figure out the P&L [profit and loss], and it was one page on Excel.

But there was this perception of when I started, everyone thought that because she came from production and my mom’s background was manufacturing that she kinda set me up with all the factories. But her manufacturing background is actually in plastic bags. So, yeah, I want to set the record straight. I can’t tell you how many times I begged her to introduce me to garment people. And she definitely helped me to try to look, it just wasn’t her area. It’s such a different industry, you know? So I would call up factories that I knew of in Midtown from my previous internships and places that maybe had connections with a factory in China. Again, it was a lot of trial and error.

You interned at “Vogue” when you were a student at Parsons, right?

Yes, I started at “Teen Vogue,” and then after a year of interning, there was an opening at “Vogue” and I was like, Oh my gosh, I have to go interview for this. I was thinking, I want to see couture, I want to see Grace Coddington, I want to walk by Anna’s office! I got it, and it was such a big deal for me. I started interning in the accessories closet, and I was also working in retail at Barneys on the shoe floor. And so that was such an interesting moment because I got to see how the customers interacted. I’d unpack new deliveries, check them in, assist the buyers with the sell-throughs. And then also on the back end, seeing editors calling in stuff, dealing with advertisers… all the politics of that. It was such an interesting perspective to see both at the same time after I had just also come from interning [at Marc Jacobs] on the design end. So I think that moment when I got to see all those angles was really inspiring for me to go and do something.

Right, and then you started with sweaters, but then the whole thing took off.

Yeah, it wasn’t overnight. Definitely one season of knit sweaters went to a season of “let’s do a whole line of knitwear: knit jackets, knit dresses, knit bottoms.” And then when I felt it was time for me to launch the full collection, the showroom at the time, they didn’t want me to do it. And I said, “I feel like I’m ready for the next step.” So I was showing the ready-to-wear, except it was two samples that I was carrying around in a backpack. I probably brought them in on plastic hangers. I remember we had a meeting with [Style.com’s] Candy Pratts Price, and I brought the samples on plastic hangers and she was like, one word of advice… “Never bring your samples on plastic hangers.” I was like, Ohhh my God. Anyway, from there I launched the full collection around 2006.

So what do you think has been your defining moment or moments from the past 10 years?

The most significant was the moment when I opened my first store [in New York]. That moment felt really special. The CFDA win was kind of a big moment, when I was really put in front of the real players — Anna [Wintour] and Diane von Furstenberg. So that was really very intimidating, but of course exciting at the same time.

Did they remember you from your internship?

Yes, Anna did. And it was a funny story with Diane, too. When I first came out with my sweater line, a designer in her office read about them, and she called me in to meet with her to freelance as a designer. I said, “I’m very flattered by the opportunity, but I’m very committed to this project right now.” And then she ended up being on the panel and then becoming my mentor that season when I won the CFDA.

You said no to DVF! I think that’s what people like about your brand so much is that you’re true to yourself.

I was very true to myself. I’ve made a lot of friends, but you have to be aware that there are people out there that aren’t always there to support you. They kind of want to bring you down or want to label you or pigeonhole you. It’s just important to be aware of it and find your balance of working in the industry, but also having privacy and having the relationships that you cherish. I think that’s what I’ve learned the most over this course of time.

Speaking about friends, you obviously have accrued a huge celebrity following, which is part of the allure of your brand.

It’s surreal. I have to say, it’s a lot more glamorized on the outside than actually the reality of it. Fashion is an industry that’s a scene, obviously, and viewed as something that everyone today wants to be a part of, whether it’s a musician, an actor, you know what I mean? And so even people that I’ve never met before will say my name in a song, or… It’s very flattering, but people are always like, “Oh, he’s friends with this person and he hangs out with these people.” My closest-knit group of friends are still the people that I spend the majority of my time with.

Zoe [Kravitz] is probably the one person that I’ve met and is actually someone that I really hang with. We see each other every time she’s in town or I’m in town. Other than that, it’s very glamorized. It’s very flattering that there are these people that I respect that know my name and my work, but it is a facade. It is what it is. [ Laughs]

Sure, it’s all part of the business of fashion, but it was fun seeing you bopping around in that Madonna video.

I mean, who says no to Madonna? She asked me, “Do you want to be in the video?” I was like, Uh yeah. [ Laughs] She didn’t tell me anything. I got there and she said, “OK, the whole concept of the video is like you have to repeat ‘ Bitch, I’m Madonna,’ but I just want you to do it how you would do it.” And I did it and she said, “OK a little bit more angry, a little bit more aggressive.” We literally did about eight takes. Then she goes, “OK, now dance, like shake your hips! I want you to just look like you’re having the best time!”

Other than dancing with Madge, what do you do when you have free time? What are your hobbies?

My hobbies are very generic. It’s like going to the movies, just spending time with friends. I get to do so much at work. Like my exposure to new things is so stimulating. Every day is different, every person I meet, every experience is so new to me that I feel very fulfilled in that arena. A lot of the times it’s kinda like at the end of it I just wanna, like, just go chill with my friends and sit on the couch and watch reality TV [ laughs] and pig out on snacks. I mean, I love traveling.

Do you have guilty pleasure shows?

I mean, I love the “Housewives.” And I’m really into “ I Am Cait.” Every episode, I think I can’t believe this is reality. It’s so incredible. And I keep thinking Caitlyn Jenner is the new Oprah. She’s going to be the new Oprah. Because you just see her learning and the way that she communicates and interacts with people. It feels like, Oh, my God, the Oprah of the next century is going to be a transgendered woman. Can’t you totally see her having her own talk show?

I’m sure Ryan Seacrest is all over that. Do people stop you on the street now that you’re a famous designer?

Sometimes. When people are very confident, they want a photo, and they just go for it and then you’re done and it’s off to the next thing. If I’m at a concert or something like that and I see people and all the sudden that person has been there when I was in that area and then they followed me to another spot, it’s like I’m not up for it.

But I know what it’s like too, to see someone that you respect or are a fan of their work. … When I meet Beyoncé, my hands are shaking trying to do her fitting. [ Laughs] There’s no way that you can contain that. You try to play it cool, but it’s just a natural humanistic reaction. I guess when you see someone that you really are a fan of what they do, it’s natural, so I understand that.

You’ve mentioned Beyoncé and Madonna, but those are very surreal moments, aren’t they?

Yeah, for sure. I think the more they feel unguarded, the more I feel comfortable. And it depends, the environment that’s surrounding them. People have their own lives and have their own flaws and stuff like that. If she’s just come off stage and there are a bunch of paparazzi backstage and you’re like, Oh shit, I have two seconds and everyone’s watching.

You’ve enlisted an incredible roster for your charity initiative for DoSomething.org. How did you get involved with that?

So when we started talking about the 10 year coming up, we were like, OK what is our goal? What do we want to do? And there was a lot of discussion of plans and a big one was giving back. And I felt that having a youth organization was important to me, and that kind of support giving youth options was really important. So DoSomething.org was the one that we landed on. So we felt like, let’s do a campaign and bring together people that we really respect or who have been a big part of our brand, who helped support us, who’ve given us support, been supporting us all these years. And from all different kinds of fields — music, modeling, acting, comedy, etcetera — to just bring as much awareness to this organization. So that was really important. And we started reaching out, just cold calling. Then Steven Klein got on board, and we shot in London, L.A., and New York.

Now that you’re moving on from Balenciaga, are you excited to focus on your own line?

Yeah. Definitely. I had never been an employee. I went straight into my own company, and so it was such an incredible opportunity. I feel like we’ve accomplished so much. I think given what I was able to do and what I’ve accomplished with my team… we’re so happy that we were able to grow the business double digits every season.

I just feel like those are the kind of very gratifying points for me. And I feel like I’ve learned a good amount. And in the long run it was a great moment for both sides to come together, but in the long term it’s like, OK, I need to go back, and they need to find someone who is really going stay with them for a really long time. I’m not ready to divulge yet, but there’s a lot of exciting things coming [for the Alexander Wang brand].

Are you doing a baby line? Is that happening?

Not yet. [Laughs] We put up that sonogram on Instagram to launch the mini-bags. Everyone thought I was launching a baby line. [Laughs] It was like, oh that makes sense, since North West came to the show.

North West, but also your very stylish niece.

Yeah, my niece, yeah. She is a diva. She came last season, but she didn’t come for two seasons prior to that because now she’s aware. She’s 5 ½, and she’ll be getting her outfit ready and ask, “Oh are people going to take pictures of me today, Mom?” I was like oh-kay, we are not taking you to the show, you’re staying at home, baby girl.

So I guess she’ll be skipping your big anniversary party…

Yeah. We’re doing our shows at 9 p.m. on Saturday and it’s going to go directly into the party. It’s going to be fun.

What’s the best party that you’ve been to that wasn’t your own?

That wasn’t the best party, but the most surreal party was this traveling German rave that came to visit New York as a pop-up. And we went, it was in the back of this alleyway entrance, we went downstairs, we were there till 6 a.m.… The music was so loud the ceiling was crumbling down on us. It literally felt like we were in Berlin. In the morning, they made us go through the front entrance of the building so we exited the front entrance and it took us to Broadway, and I was like in the lobby, and I was like, Oh my gosh, this is our new office building that we just moved into! We didn’t realize that the Ping-Pong school downstairs sublet illegally for parties. I don’t know, I’ve had really crazy times. I went to this crazy party in Thailand over the New Year. It was on the beach with I think 200,000 people. It was one of those full moon parties, and it was a rave in the forest and on the waterfall. I recommend everyone to at least have that experience once in their life.

What are you currently listening to?

A lot of things. I mean I’m obsessed with the Weeknd right now. I love all of what he’s doing. I love underground hip-hop music, I love trap music, a lot of DJs again.

Are you a social media maven? I know you have Instagram, and you’re very good about incorporating social media into your business.

In the very beginning I was very afraid of social media. Everyone was saying how important it is, and you feel this pressure to do it. To find your own voice, I think is very important. Today I’m really excited because I feel like we’ve started to really find our way of communicating with our audience and doing things and creating content that we all, as a team, get very inspired to do. The little GIFs and the things that create humor, that create irony. Even when we do a product shot, that there’s some kind of new little content to it. I love it now.

And it’s obviously there’s a business focused social media initiative, and then in your personal life, are you into new apps or anything like that?

Yeah, I’m so not tech savvy. I am the kind of person that’s like, Oh, my God, my computer’s not working, what do I do? And then the email’s not working. And then someone will say, “Have you tried turning it off?” I’m like, Oh no. … I’m very loyal to my apps. There’s Uber and Shazam and Instagram. Shazam is important for music. Uber for me to get around, and Instagram for me to feel like I’m connected to what’s going on out there.

We’re assuming your personal account is private.

Yeah, I do have my own account. It’s funny when I meet someone and they’re like, “What’s your profile? You only have 82 followers?” [ Laughs] It’s intentional because you know again there are certain things that you want to keep private. I need some censoring.

Do you read your reviews when they come out?

I’ll be honest, I do read some. I have tried to read less and less because I know myself. When I feel really good about a collection or what we have accomplished as a team, the more I can maintain that focus, the healthier for my mental state. But I feel like sometimes it’s important to cancel out some of the noise in my head. It’s not completely avoidable, but when you’re in a fitting and you think, Oh wow, do I want to do this? Oh, but there’s that one time that editor said this about my collection. You start second-guessing yourself, and that’s the worst thing that I think people do to themselves is second-guessing your instincts.

What’s in store for the next 10 years? No pressure.

[ Laughs] Gosh, I don’t know. I feel like I’m in the same spot as when I started. I’m excited, I’m ambitious, I’m ready to work hard, I’m ready to learn, I feel just more than ever the same… You know that moment you want to learn and you want to do stuff? I can’t completely say everything that is ready because it’s not concrete yet, but it’s beyond fashion, it’s beyond clothes that you wear. The brands that I respect, whether it’s Ralph Lauren or Apple or whatever, they are brands that don’t limit what their capabilities are. Ralph does restaurants, Armani does hotels, you know what I mean? I want to keep an open mind.

Do you see yourself going in the direction of a Michael Kors in terms of an IPO?

Never say never. But right now it’s definitely not a pressure that I want. I’m very focused on building our own brand first. We’re 100 percent family owned and right now I feel very stimulated and inspired by being in the driver’s seat. That’s very important to me, for sure.

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