Nickelson Wooster is a free agent. Positioned in the burgeoning no-man’s-land somewhere between ‘creative’, ‘style icon’ and ‘consultant,’ he is the instantly recognizable man-about-town. He is the silver-haired Kansas-born New York resident whom no tradeshow or fashion week is complete without a candid, cigarette-toting streetsnap of. The ubiquitous face of Pitti, Paris, Milan and now New York, he is a free agent.

A multi-disciplinarian and key figure in the new, social-media driven menswear industry, Wooster has cast his trademark reflective lenses over collaborations with everyone from The White Briefs to Cadillac within the last twelve months alone. Simultaneously well-traveled and hard to pin down, the 55-year-old is one of many indefinable and enigmatic characters who are at odds with what previous generations came to expect of the fashion industry. Mostly though Nick Wooster is, even according to himself, a “free agent”… but what does that mean exactly?

“I just made it up. It basically means that I get to do whatever I want” laughs Wooster as we chat in a Hong Kong restaurant (he is in town to promote a campaign with local retailer Lane Crawford aptly titled ‘Who is Nick Wooster?’) “I obviously have many bosses, in a way, but the idea is that rather than being held down by one discipline, or one silo, I can just do what I want. I’m not just a designer, I’m not just a retailer, I’m not just a street style person, whatever that is, I can instead do a little bit of everything.”

I am fortunate enough to work with a lot of brilliant, talented people.

A little bit of everything is exactly what Wooster seems to have been doing for as long as memory can serve. Cutting his teeth in retail at Barney’s New York, Bergdorf Goodman and Calvin Klein in the early ’90s, he went on to work as design director for Polo Ralph Lauren and form his own agency, Wooster Consultancy in the latter part of the decade. He has consequently worked on projects with everyone from Thom Browne to JC Penney, in a short-lived period as the fast fashion chain’s Senior Vice President from 2012-2013.

“I am fortunate enough to work with a lot of brilliant, talented people. At the end of the day, I am so appreciative of the fact that I have a choice, that’s the main thing. It’s basically a different way of saying ‘consultant,’” he adds on the subject of the ‘free agent’ self-branding.

This organic, if somewhat sporadic, approach to a career in the fashion industry is one that is becoming increasingly prevalent. Wooster is perhaps the most recognizable in a long list of characters who are breaking into fashion through non-traditional career paths. The man, who has previously referenced his personal Instagram account as his 401k, sees this as an industry-wide shift, rather than just a flash in the pan. “I honestly do think that it’s a little bit of a template for how younger people are going to structure their careers” he explains, “when I started 32 years ago, it was very linear. You started something and followed a pretty direct path until you got somewhere. For kids, brands, companies, all bets are off. Companies are changing, kids have a different set of values and idea of how they want to structure their lives.”

Social media has certainly made everything more immediate. There’s good and bad aspects.

Where, to previous generations, Wooster’s short tenures at each of the brands on his resume would be viewed as failure, that is simply no longer the case. 2015’s desire for more, faster, easier means that characters such as he can chop and change projects monthly, even weekly and be deemed a success.”It’s probably going to be best for everyone if people just work on projects” offers Wooster on the rapidly changing dynamic, “maybe that project will last 10-12 years, or it might not. It might be a few months, it might be a few weeks, and I think that’s where it is really different from 30 years ago.”

But what of social media? Does the creation of esteemed industry professionals through the utilization of a point-and-click photo app devalue the whole thing? Where once we looked up to designers and brand directors who had served their time from the mail room up, Internet sensations can now elevated to God-like status by putting together a neat online portfolio through Instagram. Wooster is less forthright on this subject, perhaps shielding himself from being drawn into this much-maligned group of millennial entrepreneurs. “Social media has certainly made everything more immediate. There’s good and bad aspects, I’m not going to argue if it’s right or wrong, good or bad” he says, his voice little more considered and measured than earlier, “I do think that it’s changed the pace of how we consume. Not only merchandise but images and words, how we consume news and information. I don’t know where it is all gonna lead, and I’m not sure anyone truly knows at this point, but I do think that the immediacy of it has kinda lifted the veil on what it takes to get somewhere.”

We’re churning through ‘stuff’ way faster than we ever did.

The truth is however, once you’ve met Wooster and heard him talk with humble confidence about the industry he has inhabited for over three decades, his credentials simply cannot be called into question. Whether it’s working on the floor at Barney’s or rubbing shoulders with menswear’s elite around the globe, you are reassured that he is very much grateful for his lot and understands there are people eminently more qualified to help his career along the way. Whether you believe him to be qualified for the lofty position he has reached or not fades into further insignificance when you consider the co-signs along the way. Could Ralph, Thom Browne, Calvin Klein and United Arrows all be wrong? More than likely not.

“There’s a lot of stuff that goes on behind the scenes and I think social media has perhaps done a disservice to the people who make it look like magic” he adds, as our chat draws to a close. “They make it look effortlessly simple. It still requires the same hard work and the same knowledge base at the end of the day, but the tempo has accelerated for sure. We’re churning through ‘stuff’ way faster than we ever did and I guess along with that goes life cycle of brands, publications, life cycles of businesses and certainly careers.”

It seems at this point that Wooster has said all he has to say on the matter. He has shown he implicitly understands the industry in which he is extremely grateful to work, shown that he is by no means the caricature of scowl framed by quiff, sunglasses and cigarette that we have led to believe and, in one way or another he has answered the question; Who is Nick Wooster?

Nick Wooster is, and probably always will be, a free agent.