There was a moment before the helicopter took off, my hands pawing along the perimeters of the hole in the side of the aircraft where a door should have been, when I truly felt like I understood regret. I regretted pitching a story about extreme shoe selfies. I regretted agreeing to test out the helicopter photo service that promised “a #shoeselfie” opp as one of its main features. I regretted not pushing back when the shoe brand that had sponsored the trip asked me to wear a popular pair of stilettos for the trip instead of the sensible flats I had initially picked out — heels so delicate, my nervous self had trouble on flat land, nevermind the floor of a doorless helicopter (did I mention that the thing doesn’t have doors?). I regretted sitting in the seat closest to the door hole. I regretted not putting deodorant on my hands, which were sweating so hard, I had trouble working my phone, which was the entire point of this stupid, stupid, stupid flight in the first place.
Most of all, I regretted the moment that I had first let myself be persuaded to “do it for the ‘gram.” I had never staged a photo on Instagram before — I ate the meals I took photos of, and liked whatever I recommended. I prided myself on keeping it real. But now dangling my feet out of the side of a six-person chopper for a single photo? I had found my limit, and it was too late to abort.
I was on a doorless helicopter (doorless!) because I was trying out luxury footwear brand Tamara Mellon’s newly launched sweepstakes, where winners receive a free vacation and helicopter ride — a chance to take a #shoefie.
If this feels random, you haven’t been paying attention. The extreme shoe selfie has existed among sneakerheads for years, ranging from hypebeasts setting their rare sneakers on fire or rooftoppers trespassing onto skyscrapers and bridges for a shot. It wasn’t long before brands took notice. “I’ve been in meetings where the pitches have been ‘drone taking a sneaker selfie while they’re hanging off the Eiffel Tower,’” former Complex sneaker editor Gerald Flores tells me. Now the marketing trend has expanded from athletic shoe brands to women’s labels like Tamara Mellon, which paid for the flight and shoes for my own extreme shoe selfie.
Tamara Mellon's initiative builds on a growing trend in marketing where brands tap thrill-seeking photographers who embody the same values of adventure, wonder, and fearlessness their products claim to represent. The thrill that comes from being recognized on social media — compounded by their daredevil spirit — have made extreme shoe selfie photographers a natural partner for shoe brands that can provide exposure, freebies, and even sometimes cash in exchange for cultural cache in the form of stop-you-in-your-scroll content.
Take Tom Bruise for example. A year ago during a New York blizzard, Bruise (not his real name) got a call from a friend asking if he wanted to climb the Manhattan Bridge. Bruise had a taste for flouting rules, but he hadn’t ever ventured into something this illegal. When he made it to the top, the bug bit hard. “I was like, ‘This is where I need to be at.’ I can’t describe the feeling. It’s excitement, a crazy rush. You don’t feel like you’re on this planet anymore.”
Since then, Bruise has scaled about 80 separate buildings — sneaking past the front desk, picking locks in stairways, and scaling scaffolding and spires to take mind-meltingly terrifying shots. His passion is beginning to turn into a livelihood; he’s been tapped by shoe and clothing brands to rep their gear in his Instagram photos, and some have even paid him for images to post on their own accounts.
For Bruise, rooftopping is about euphoria. Others cite a Robin Hood mentality — accessing rich people’s domains to steal views to share. But most, even if they don’t admit it, do it for the ‘gram: “Regardless of what they’re trying to convey, they’re all still driven by scrolling down that feed and seeing those hearts pop up,” Flores, the ex-shoe editor, tells me.
Victor Thomas, who goes by Vic Invades, is another rooftopper in New York. In Thomas’ shoe selfies, he hopscotches between reinforcement bars or casually perches on a rooftop ledge like he’s waiting for pancakes in a diner. He wears his own Vans and Nikes, and also promotes shoes that have been sent by brands like Patos and Converse. He is thoughtful and surprisingly emo for someone with such a predilection for shock-value — his Instagram photos are captioned with things like “If you never cried about it in the shower, you never loved it.” On one post, he asks his followers to comment what they feel when they see his photo. The responses flowed: “Anxiety.” “Peace.” “Getting used to being stronger.” “A desire to reach the same heights in my own life.”
The metaphor is not lost on Thomas: “For people like me, who live in a small brownstone or in my projects building, they don’t get that experience [of being high up],” he says. “I steal certain views for people who normally don’t get to see those views. It’s all inspiration so people can say to themselves, ‘Maybe I can reach some heights, too.’” Thomas’ photos have gotten him jobs, earned him money, and given him a level of notability — he collaborated with The New York Times on a video about his escapades. “I want people to know they can come from the bottom and go higher.”
Both Bruise and Thomas have been arrested for their climbs, and others have been slapped with criminal charges: An urban explorer known for photographing abandoned spaces was charged with misdemeanor trespassing by authorities in Cleveland. When asked about unauthorized photography atop public structures in New York City, including those involving brand sponsorships, a spokesperson from the New York Police Department responded: “A person found in violation may face criminal charges.”
Not all death-defying Instagram photos are illegal. Some are perfectly by-the-books while being perfectly terrifying. That’s exactly the type of aerial photography experiences that FlyNYON offers — and that Tamara Mellon’s campaign tapped in its new campaign. A 15-minute flight in one of its doorless choppers costs $241 ($219 if you book online), but it grants you a unique opportunity to stay within the law for an aerial snap of the city. Brands are noticing: Superga and Saucony have both worked with FlyNYON for photo-op partnerships.
Like rooftopping, there is a community of helicopter photographers. Natalie Amrossi, who posts photos at @misshattan started taking photos from the tall vantage points from the offices of her employer at the time, JP Morgan. Now, she gets invited onto rooftops; unlike some of the others, she doesn’t have to break in.
More recently, aerial photos she took through FlyNYON have landed her invitations to shoot with different helicopter agencies around the world. Louboutin tapped her for a partnership: “For that, I crossed my legs all ladylike so you could see the red bottoms,” she says. “There’s also a cool way where you position your legs straight on, but a little bent. I call it Inception — like you’re falling into the city.”
I remember Amrossi’s advice while I drive the 40 minutes from Manhattan to FlyNYON’s hangers in Kearny, New Jersey (just enough time to contemplate what exactly was wrong with me that I agreed to do something like this). There, I watched a safety video and a thorough explanation of the harnesses for myself and my phone that’d keep me from becoming a flesh splatter, which offset the trepidation I felt from the youth of the FlyNYON employees, many of them sporting the beleaguered efficiency of amusement park operators.
But, after all that, I was inside. I had been strapped in and hooked on. There was no abort button, short of cutting through my straps with the knife each person had strapped to their chest (comforting much?). An attendant kindly taped over the release lock of my chest harness, “so you don’t accidentally, you know…” she trailed off.
The chopper lurched up without warning, and then the wooden pallet that we had docked on became the size of a sandwich board, a Wheat Thin, a pinprick… The wind whipped my bangs so hard I became convinced that my individual hairs could give me paper cuts, but at least the wind dried my sweaty palms, and I was able to unlock my phone. Two minutes later, we were hovering above Columbus Circle.
Readers, the view. After a certain height, the real world looks as unreal as a screen. I realized, with some uneasy familiarity, that looking outside the door hole wasn’t unlike watching Netflix in my favorite position, where the laptop is perched right on top of my supine chest. But instead of a sitcom, it was the city I had lived in for almost ten years, in a way I had never imagined it could look. Times Square was a tiny crumb of lights. I looked the top of the Freedom Tower in the eye. The entire city was a patchwork of rooftops and spires, providing a view that only the very brave or the very rich are able to see from.
And yes, I took about a hundred photos of my feet, falling Inception-style, and with one perched on the other leg’s knee, Instagrammers-at-brunch style. The Tamara Mellon shoes were cute enough on land, but in the sky, weaving in and out of the mist, they felt like a trophy. I couldn’t stop taking photos of them. My shoes were an infant, and I was a new mom. My shoes were a teen heartthrob, and I was a Belieber.
But once we landed, and I had climbed back into a car to make the drive back into Manhattan, I realized that the real rush was yet to come.
I posted a photo, and waited.
Watch Connie's shoe selfie adventure below: