Image courtesy of New York Natives, photographer James L. Knobloch
By Chris Vespoli

“Now this is the part where we take digitals, where you actually have to take your shirt off,” renowned fashion model Shaun Ross informed me all in one breath while seated like a Victorian prince in a plush, high-backed chair.

I heard myself say, “that’s not a problem.”

Except it was a problem. My pale, doughy man teats, pepperoni nipples, hairless chest, and bulging belly had no business going uncovered, especially not in front of a roomful of strangers who had been looking at toned, supple model flesh all day. But nevertheless, I obliged Shaun’s request and peeled off my T-shirt. I was the one who had put myself in this position, after all. I wanted to know what it was like to be a member of the fashion elite, and there was no better way than to experience the rigors of the model casting process, standing shoulder-to-shoulder (well, shoulder-to-knee in my case) with the tall, chiseled male and female specimens who were vying for spots on the runway.

It was all part of my edification as I prepared to survive the social anxieties of Mercedes-Benz Fashion Week in New York, an ostentatious affair I thought I’d never be a part of…again.

Model Casting Photo 628x837 Awkward New York: Shaun Ross Taught Me How to Fashion Week
Image courtesy of New York Natives, photographer Daniel Parker

I experienced my first Fashion Week last September, on special assignment for this website. My mission was to endure the twice-a-year, weeklong orgy of glitzy runway shows, exclusive parties, and drunken wannabe socialites (as I had described the scene in my report) from the extreme outsider’s perspective, seeking out as many awkward situations as I could get myself into. I learned a lot by observing the fashionistas, but not nearly as much as I could have if I had tried to blend in with them and be a part of their world. I had merely played the part of a fleeting tourist when I really should have been hunkering down and living with the natives…the sparkly, thin, well-dressed natives. Luckily, I didn’t need to wait long for another chance to get it right. I was going back to the “tents” in February a little older, a little wiser, and a lot fatter — and, this time, as a bona fide Fashion Week guest.

Invitation Email Screen Grab 628x443 Awkward New York: Shaun Ross Taught Me How to Fashion Week
Image courtesy of New York Natives, photographer Chris Vespoli

I received my first of many official Fashion Week invitation emails on Jan. 21. I remember the exact date because it was the first time I had been invited to anything cool. That’s not to say I’d never been to cool things before. My media career had taken me behind the scenes at Saturday Night Live and Conan, and backstage at The Daily Show. But that was for work — I was expected to be at those places because I had jobs to do there. Fashion Week was different. People were asking me to attend their big, fancy things. There’s a quantifiable difference between someone demanding you show up somewhere and someone hoping that you’ll come, and I had every intention of coming and making a good impression.

That’s where Shaun Ross came in, the world’s first albino African-American male model, and one hell of a good sport.

Our Director of PR (and former reality TV star) Stef Skinner was good friends with Shaun through her work with People’s Revolution, the high-powered PR firm helmed by fashion icon Kelly Cutrone (if you hadn’t noticed, I’ve already mastered the fashionable art of name dropping…like a douchebag). Adding to a long list of credits that includes modeling for Vogue Italia, Paper, and Alexander McQueen, Shaun was prepared to take on the biggest challenge of his young career: teaching a short, nerdy, style-blind heterosexual man how to dress, talk, and carry himself at a Fashion Week event. That’s how I ended up shirtless in the middle of Shaun’s model casting. That’s also how I ended up in a studio in the Garment District a day before that, with most of my meager wardrobe strewn on the floor as Shaun chastised me for my unflattering taste in plaid flannel, while trying to help me find something — anything — that would be halfway appropriate to wear to a runway show. And that’s also how I ended up at the Skingraft runway show a week later, with Shaun, putting everything I had learned to use.

Skingraft Press Pass 628x471 Awkward New York: Shaun Ross Taught Me How to Fashion Week
Image courtesy of New York Natives, photographer Chris Vespoli

I won’t attempt to recap all of the cringe-worthy details of my crash course in fashion; the video above the fold does a more than sufficient job. What I will offer here is the singular takeaway from my second foray into New York Fashion Week:

I missed the mark.

No, not in my execution of what Shaun taught me, but in how I approached the lesson from the very start. I had thought I needed to learn how to become part of the crowd, to fit in. “Living with the natives.” But in my wanting to be a part of the fashion crowd, I had forgotten the very important distinction between integrating and conforming. Shaun didn’t want me to conform. He wasn’t my fairy godmother, heaven sent and bent on transforming me with a wave of his hand into a gussied up lie just in time for the big ball, only to return once again to my true form come midnight. No, he wasn’t trying to make me into something I was not; he was just trying to get me to see myself in a way that I had never considered…and to stop dressing like “a 27-to-30-year-old lesbian,” as he bluntly characterized my style.

Shaun taught me Fashion Week isn’t about fitting in with everyone; it’s about doing what’s not expected, and oftentimes, the most important person you surprise is yourself. You wear a black shirt with a black tie instead of a white shirt, a blazer with a pair of Vans instead of wingtips. And you don’t ditch your thick-rimmed prescription glasses or cut your shaggy hair, because those are the types of things that make you stand out, and standing out is good. Again, it’s what’s not expected.

There is an inherent contradiction in this rationale, of course. When too many people choose to go against the grain together, the unexpected becomes the expected once more. What was once daring becomes safe; what was once unique becomes mundane. Instead of a linear progression of taste, fashion is a Möbius strip of cyclical trends in which every style, every color (especially black), and every one gets their turn in the spotlight. The entrance to Fashion Week isn’t a turnstile; it’s a revolving door. What’s hot today is out tomorrow and back again…but never plaid flannel, apparently.

Shaun Ross will kick your ass if he sees you in that shit.

Fashion Week Wardrobe e1424376868915 628x628 Awkward New York: Shaun Ross Taught Me How to Fashion Week
Image courtesy of New York Natives, photographer James L. Knobloch