Nick Wooster Tells Us How He Became a Style Icon

Photos by Bobby Viteri

If you’re into fashion, chances are you know Nick Wooster. Or at least what he looks like. He’s a street style fixture, thanks in no small part to his distinctive, adventurous personal style. Steel grey hair swept up in a modern day pompadour, tattoos covering his arms and legs, Wooster wears the kind of mash-up outfits—disparate elements like drop crotches, florals, tailoring, and high-tech sportswear, sometimes all at once—that could be ridiculous on someone else, but somehow, on him, look perfectly natural.

But that’s not the only reason Wooster draws the lenses of fashion week photographers. The man doesn’t just look the part; he lives it. The 30-year fashion industry vet has logged time everywhere from high-end department stores like Barneys and Bergdorf Goodman to major brands like Ralph Lauren and Calvin Klein. Now, he’s a self-described “free agent,” consulting for a stable of brands while racking up more than half-a-million followers on Instagram. Since we’re in the midst of another New York Fashion Week—where Wooster is always omnipresent—we caught up with the tastemaker and style expert to talk about his rise to fame, how his career re-ignited at age 50, and the illusion that you can build a career out of social media.

VICE: You grew up in Salina, Kansas. What was that like? Did you stand out?
Nick Wooster: Sure. That’s the reality when you’re a gay kid in Salina, Kansas in the 1970s. I didn’t necessarily know what it represented or meant, I just knew that I was a little bit of an alien there. And I knew I had to grow up fast and get out of there quickly. I viewed my adolescence as marking time. I was just waiting to leave.

When you were younger, did you have the same sort of interest in clothes that you do now?
Of course! I cared about how I dressed, and I wanted to wear the nicest clothes that I could get my hands on. I wanted cashmere sweaters, nice white shirts, chinos, topsiders. And I was concerned about quantity. I wanted to never wear the same thing twice. When I went into middle school and high school, I noticed the richer kids that had nicer clothes, and I was like, “I want that.” And my mom said, “Great. Then go get a job and make money and buy that, because we’re not buying it for you.”

After that, you went to the University of Kansas, and then it was off to New York. But it took a few years before you started working in fashion.
Right. I studied advertising in college, so from ’83 to ’85 I worked at an advertising agency. In 1985 I started selling advertising space at New York Magazine. I got fired, because they diagnosed my drug problem long before I did. And I was not cut out to sell advertising space. You know, hats off to those who can, but that was not for me.

When did you become sober?
I just had my 20th anniversary last week. September 3rd of 1995 is when I actually stopped. But I knew in the summer of 1991 that I needed to. It was four years of a little bit of fact-finding before I could figure it out.

So you got let go from New York Magazine. Then you moved into fashion, working at Saks Fifth Avenue as an assistant department manager, after which you were a buyer at Barneys and then Bergdorf Goodman. Then it was retail at Calvin Klein, followed design at Polo before you moved on to be president at John Bartlett. That covers 1986 to 2001. So you’re well versed on both sides of the business: the selling of clothes, and also the creation. How do you balance the two?
Editing, being able to look at things, trying to make a business out of something, that’s what a good merchant does. But the idea of building something is the other part that’s really fun when it comes to this world for me. I never thought of myself as a créateur in the way of people like Rick Owens or Thom Browne or Rei Kawakubo, who are truly doing something. But when it comes to ideas, that’s the niche I see myself in: interpreting ideas. Making product is, for me, the missing half of my career.

At John Bartlett, what was great about those five years was the opportunity to really build a business using both of the skills I had put together so far. Because at the end of the day, you can have all the great ideas in the world, but if they don’t sell, then it doesn’t keep going forward. So I was utilizing both corners of my experience, to hopefully do retail right, but at the same time work on exciting product. And that’s really what I look at my career today as: the ability to toggle back and forth between the two.

You left John Barlett in the wake of a restructuring. That wound up being a major step in your professional life.
Yeah, that was where my career really changed. I couldn’t find the next right job. And that’s why where I am today is so shocking to me. Starting in the fall of 2001, I did anything I could to stay afloat. That involved me moving to Miami, working in a car dealership—long story, I didn’t sell cars—then moving to LA, having a couple of false starts, working on the floor of Barneys in Beverly Hills, and then, eventually, working for two companies for a few years. I was perfectly happy going along with my life, living in LA, thinking that the life I had before wasn’t going to happen again.

But that wasn’t the case. You found yourself back in the thick of it in 2010 as the men’s fashion director at Neiman Marcus and Bergdorfs.
It was later, in the fall of 2009, when I read that Tommy Fazio had left the men’s fashion director job at Neiman Marcus and Bergdorf Goodman. So I called people that I used to work with at Bergdorfs, and they told me who to contact. And I cannot overstate this: No one was more surprised than me that I got that job. But I got it. At 50, to have that life start, continues to be very shocking to me.

Was it jarring moving back into that sort of role? Or did it feel natural, considering your past experience?
When I stepped back into it, for me, it was completely normal. People like Bruce Pask, Jim Moore, Nick Sullivan, they knew me from before, but for a whole generation of kids, they were like, “Who is this guy?” Still, I’ve said this before, and I believe it: I do feel like I’ve earned where I am today. I worked for it. I’ve earned every line on my face, every grey hair. I think one of the problems that social media—the world of Tumblr and blogs—has created is this idea that it’s all instant, and that it’s all easy. It can be for many people, and hats off if that’s your path. But the part that nobody understands when they look at Instagram or a blog post is that something had to happen behind that picture or those words. And I’m here to tell you that I did it that way. I earned it the hard way.

Social media has created this idea that it’s all instant, and that it’s all easy. But the part that nobody understands when they look at Instagram or a blog post is that something had to happen behind that picture or those words.

There was a fallout with Neiman Marcus and Bergdorf’s eventually, reportedly over some quotes of yours in a GQ story. Were there already cracks in the facade before that?
I did the best I could with what I had. Sure, it probably wasn’t the perfect fit. But it was the job I always wanted. So I just kept doing it because I couldn’t see that far ahead. And yes, they decided that I wasn’t right for that job. In hindsight, I’m so grateful to them. I only had to do that for a year and a half; it was really fast. Obviously at the time it was pretty devastating, but I should have been more careful. It’s nobody’s fault except my own. They did what they felt was right for their business. And it worked out.

Because that’s when you worked with Thom Browne, Gilt Groupe, and the Project trade show to start building a presence for your personal brand.
They helped me a lot. I needed money, of course, but it was great to be around people in a universe of opportunity, so I wasn’t just sitting at home worrying about what was going to happen. And it gave me a lot of exposure.

And that was right around the point you struck out on your own again.
It had been suggested to me at exactly that moment that I should be doing something on my own. And I said no, because I had always been programmed that I needed to work for someone else. But what I know now is that, yes, I am able to do something on my own in a way that I never could have imagined before. I think that the nature of employment is changing in front of our eyes. And if anything, I am a template for how people who had a corporate existence can and possibly will work going forward. I think people are looking for more varied experience. That’s exactly how I would describe my career path. People have asked, “Why did you do that?” I did it because it was interesting! Not because I was clever. I wanted to do the next thing.

And that next thing now is being a free agent. A popular one. Now that you’re consulting on so many things, do you have litmus test for what projects and collaborations you decide to take on?
Sure. Except that I don’t. [Laughs.] It’s like being asked on a date. With some people you know instinctively that it’s a no. But other times it’s like, “I guess I don’t have anything going on. I could eat a meal. Sure, let’s do it!” Two years ago, when I started in this place that I am today, I had no idea how it was going to work out, so I just took some jobs. Today, that’s very different. I’m able to choose, which is an amazing gift. But here’s the thing: I have no idea how long it’s going to last. So it’s all a risk, a crap shoot, taking it as it goes. But I hope that I’ve made some smart decisions, worked with some nice people, and we’ll see what the future holds. There are no guarantees. And part of that is exciting, and part of it is terrifying.

You’re working with Lardini, Greats, Cadillac, and United Arrows, just to name a few. What is it, do you think, that you bring to the table for these collaborators?
I think what I bring is an audience. That’s number one. Right or wrong, good or bad, that’s just a fact. But equally, and what I might argue is more important, is I’m very experienced. I’ve been doing this for almost 30 years—actually longer if you count all the years working in high school and college. I’ve done a lot of different things. If they want me as an endorser, have the picture taken, sure, I can do that. But if somebody actually wants to build something and understand all the steps to get there, I can bring that to the table, too.

And your personal style, of course.
I mean, it never occurred to me that anything I’ve ever done has been remarkable. Because I thought in order to work in the fashion business you had to have a certain taste, style, point of view—to understand certain rules. But yes, that kind of goes without saying. If people want to hire me or work with me, they want me to bring my point of view, whatever that may or may not be, to the table. But here’s the other thing: I can’t do it any other way. It’s all I know. They’re going to get that whether they want it or not, because I don’t know anything else.

So how would you define your aesthetic? There are things that you can wear that would look silly on other people, but look natural on you. Is there a trick to that? Or is it some sort of inborn Woosterness that elevates everything?
I think it’s just stupidity on my part. I mean, I’m afraid. I’m afraid of everything. But I’m not afraid of getting dressed. I think that getting dressed is 100 percent insecurity, anyway. You’re trying to maximize whatever is good and minimize whatever is bad. So I guess on some level I just learned how to dress for my body type, and how my body is at that moment in time. And I think having a sense of humor when you’re getting dressed is an important thing. I can look back and say, “What was I thinking?” But the point is that I’m willing to take risks and experiment. No harm, no foul. I’m sure that there are many people who think I look ridiculous, and they’re probably correct, but I don’t know how to do it any other way.

We talked about the idea that you bring an audience to the table. Is social media central to what you do?
It is, I think. It’s become that value-add that is now part of the conversation. Look, there are careers based on social media, and understanding the science, and helping companies or individuals raise their social media profile. I don’t even know how I did it. I am not that smart. But if someone is hiring me, they’re hiring me for my experience, but they’re also hiring me for my audience, and now the two are just there.

But you do have upwards of half-a-million followers on Instagram. You must have made specific moves to cultivate that following.
Absolutely not. The only thing that I’ve done is notice it. Like, “Oh, wow.” I’m aware that there are probably things that I’ve done or could have done that are damaging to building an audience. And there are probably some things I should or could do to build it, but I haven’t done either one, because I’m too lazy.

Would you describe your rise to street style stardom similarly? Was it just something you noticed? Or was there a deliberate cultivation there?
I’m not going to lie and say that I’m not aware, when I buy things or decide what I’m going to wear. There are a couple of thoughts that go through my head. “Have I worn this before?” “Would this make a good picture?” So the reality is that sure, I’m very aware. But I would be doing it anyway. And anybody who knows me can tell you that I’ve always done this. Like I said, in high school, I never wanted to wear the same thing twice, and I’m always trying to figure out a way to wear something differently. Those two things were true 40 years ago, and they’re true today. I’ve always been that person who wanted to look nice. Or better. Or a little bit different. That’s never gone away.

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