The Big Business Of Street Style Bait

Angling to get your street style picture taken is an important piece of the blogger-industrial complex. Just as Zanita Whittington.

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It is Fashion Week, and I am crouching behind an overflowing garbage can, trying to make myself invisible. I’m hiding so I can avoid getting in the shot of Zanita Whittington, who is on a mission to do the exact opposite. Pretty in a way that unnerves average humans and wearing a leopard-spotted silk dress that floats behind her as she walks, Whittington tries to make herself appear like the only person in the world. And it’s working. Photographers swarm her as she takes her time crossing a busy intersection. She graciously acknowledges a traffic guard yelling at her to mind the cars while completely ignoring him as well. “WATCH YOURSELF!” he barks, as she peers over her shoulder at the cameras, watching them as they’re watching her.
While most people think Fashion Week is about the runway shows, there’s an alternative industry that happens outside on the streets that’s often at odds with and scoffed at by the fashion establishment. It’s one Whittington has been inhabiting for nine years. As one of the most established influencers on the scene (she was on one of the last covers of Lucky magazine in 2015, along with fellow bloggers Chiara Ferragni and Nicole Warne), Whittington boasts 354k followers on Instagram and has expanded her blog with an online-learning platform for digital creatives, Azalle. But the bulk of Whittington’s business is based on convincing others that her style is something worth paying for. The photos being taken of her will eventually populate street style slideshows and fashion trend pieces for the next few months, and eventually lead to paid deals that’ll oftentimes feed images. And although each photo will appear as if the photographer captured a candid moment of a woman mid-step, most moves are practiced.
Photographed by Courtney Yates
Whittington at home with a gold bag she was sent to wear during Fashion Week.
“Street style is a huge part of my business,” Whittington tells me outside the Dion Lee show on Washington Street in New York City, explaining that the photos help boost her reputation as a style authority. For now, she’s focused on making sure there are plenty of shots.
There’s a strategy involved. Just ten minutes ago she fashioned a denim jacket into a scarf (to give photographers a new variation of her look to capture), asked her driver to drop her off two blocks away from the entrance to a show, and made an S-shaped journey, doubling the mileage she would have made if she had gone straight there. “The trick is to walk to the show,” she tells me, as I try and flatten myself against a wall to avoid getting in a photograph. “That way you get more shots in.”
Angling to get your photo taken might seem like an exercise in vainglory, but it’s an integral part of the blogger-industrial complex. By wearing certain brands that appear in viral street style photos, influencers court new business and strengthen existing relationships; it’s similar to how legacy fashion magazines favor advertisers in editorial coverage. And when every American fashion publication, brand, marketer, creative, and executive is in town and paying attention, it’d be foolish to not take advantage.
“The quantity of business opportunities rises during NYFW,” says Vanessa Flaherty, a partner and senior vice president from The Digital Brand Architects, an LA-based digital talent management agency who represent influencers. “Brands are looking at NYFW as a gateway to working with influencers as a testing ground to later parlay into longer-term opportunities.” If you play your cards right, peacocking in front of photographers can make you a whole lot of money. For digital celebrities like Whittington, Fashion Week is Sweeps Week.
Photographed by Courtney Yates
Whittington checks her calendar to see the location of her next show.
If Whittington said yes to every deal that came her way, she could earn as much as $100,000 for a single New York Fashion Week. Not that she would, of course — many opportunities are off-brand (athletic labels) or off-message (laxative teas), which means Whittington turns down more business opportunities than she executes.
This is a long way from where Whittington started. Back in 2008, she was a model and photographer who posted her outfit pics online as a creative outlet. Back then, the fashion blogging community relied on banner ads for income, but native advertising and sponsored content quickly presented a lucrative way for bloggers to earn an income. Now, she spends her days collaborating with brands on advertorials, earning enough to support the salaries of three full-time positions for herself, a business partner, and a content creator. Though Whittington works all year long, Fashion Week is Sweeps Week.
During NYFW, she generally adds around a handful of additional jobs on top of her ongoing gigs. This NYFW, she’s working on three. (Full disclosure: One of the deals was with Refinery29’s 29Rooms). This careful curation has helped her escape much of the flak that many of her peers have gotten from followers claiming that they’ve sold out. “If I have to lend my name to a brand that’s not very cool, that means I have to work really hard to make my content really interesting. A bit of their uncoolness will rub off on me, so I’ll charge them more.”
The types of deals that influencers land may range from something as simple as an appearance fee for attending an event to something as involved as a year-long campaign with a beauty brand — which notoriously have bigger budgets — of which Fashion Week becomes one chapter in a longer story. (Aimee Song, for example, reportedly earned $500,000 for a yearlong Laura Mercier deal, one of the biggest of its kind). And while Flaherty tells me that there can be extreme variation with rates, Whittington says that her street style notoriety means she can charge at least $1k per Instagram ad; she’s heard from peers who have above one million followers that they can get more than $25k.
But the majority of Fashion Week labor is unpaid, or at the very least, indirectly tied to business. Take the leopard dress Whittington borrowed for the day, a common practice among influencers. “It’s Tibi!” Whittington calls out when a photographer asks her who she was wearing, though she was not paid by Tibi to wear the brand’s dress to the show. “That’s a relationship-building exercise,” she clarifies.

I don’t want feel like I’m pimping out everything I do.

Zanita Whittington
Certain bloggers like Bryanboy have recently come out against the pervasive borrowing and lending that creates the illusion that influencers are rich enough to afford all the outfits they wear, but Whittington still relies on pulling samples from showrooms to wear once and then return. “That’s nice that he has enough money to buy his own clothes, and he deserves all the money he works for, and his value is in that. But, I prefer to return it. I don’t want so much stuff. I know that I consume too much already.” Most emails in her inbox are requests to send her products, and she declines many more offers than she accepts, especially if there’s an expectation that a gift will come with an endorsement on her site.
The smoke and mirrors illusion extends beyond just clothing — many influencers get their hotel and travel paid for too, which can save them quite a bit of money. Between food, accommodations, and transportation, things add up: “You could spend $50k trying to go to all four cities,” Whittington says.
To subsidize costs, many influencers exchange endorsements for trade, typically Instagramming vignettes from the hotel for a free week’s stay, or working with a brand on deeply engaging social content for a free flight. While some influencers are hesitant to acknowledge freebies, others like Bryanboy have made of habit of disclosing who paid for his travel — the FTC also stipulates that social media posts be clearly labeled as an #ad when an endorsement has been the result of a gift. While many influencers ignore this rule, the FTC proved that it could enforce the regulation when they fined Lord & Taylor in 2015 for improper disclosure.
Whittington says that many hotels are eager for the publicity: “If you want to, and are smart, you can get anything comped.” Small bloggers with shallower pockets will need to secure hotel and travel deals in order to attend Fashion Week, but bigger bloggers will eagerly forgo it if they can: “More recently, I’ve been staying in Airbnb, because I don’t want to do another job that can be so boring content-wise,” Whittington says while covering her face with her hands in mock exasperation. “I want to be able to have a personality with my captions, and if I have to do five or six hotel posts a week, what can I say? ‘Here I am! Amazing time! Wooow!’ I don’t want feel like I’m pimping out everything I do.”
Photographed by Courtney Yates
Whittington with the new scarf she created out of her jacket.
While waiting for Whittington outside the Tibi show earlier that day, I watched as three sweating women dressed in thick camel coats arranged themselves on the sidewalk for a couple photographers. Despite the fact that they were hamming it up in ways I hadn’t seen outside the more embarrassing challenges in America’s Next Top Model, most photographers ignored the trio.
“If people don’t know who you are, you can’t monetize it.” Whittington says of bloggers who show up to Fashion Week without actual invitations to shows. “It’s a risk trying to come and just live off exposure.” Though the street style economy is a widely acknowledged facet of Fashion Week, it’s still considered tacky to indulge in it, and even worse, to beseech it. The designers whose shows Whittington attends and is photographed outside have invited her, which gives her a reason to be there. Those without an invite sit on the lowest rung on the street style hierarchy.
At the top are esteemed editors and influencers, who don’t need additional exposure, like Taylor Tomasi Hill of Dallas retailer Forty Five Ten, or Sarah Rutson of Dutch LLC. “Photographers want to catch this rare bird, who’s just flying in there, not wanting to be photographed,” Whittington explains.
On the next tier are influencers with strong ties with brands, who understand their roles in the street-style ecosystem. Phil Oh, whose images run in Vogue, points out that the most common types of photos that magazines and publications commission are images of a woman standing straight up-and-down. Typically, the only individuals who stop and patiently pose for the camera in that way are like Whittington.
But to acknowledge that the show doesn’t matter at all will immediately out you as desperate. “The best street style photographers don’t like the idea of someone just turning up just to use them,” says Whittington. “But, not all of them are Vogue photographers. A lot of them are showing up in exactly the same way.” In more recent years, the scene has only grown. There are many more influencers than ever before, but there are many more photographers, too.
While walking to the show, Whittington gets approached by a woman weighed down by a half-dozen handbags and a camera, who asks if Whittington would take a street style photo with her product, for some on-the-fly sponcon. Whittington politely declines. “I used to say yes to so many things — and my photo would end up in ads endorsing sunglasses or drinks and stuff.” She tells me this as I watch another woman being interviewed for a video get handed a bottle of hairspray. She looks confused for a moment, then gamely grins, sprays it, and mugs for the camera. The line was crossed. The other photographers standing around her immediately put their cameras down and look for another subject.
Photographed by Courtney Yates
Photographers flock Whittington.
If you want to really enjoy the taste of sausage, do not go and see how the sausage gets made. Likewise, seeing how the glamorous shots in street style photos gets manufactured can feel gross, too. And when you pack the big egos of fashion professionals into four weeks of shows, cross-Atlantic travel, and shoes that pinch, things like a slow-walking influencer can make grown women go bezerk. Such was the case last year when Vogue took the street scene to task for changing outfits too many times in day.
In an article that recapped the Milan Fashion Week season, Vogue’s top editors roasted the modern street style scene, even though the publication regularly commissions and runs street style photos on the site.
“Note to bloggers who change head-to-toe, paid-to-wear outfits every hour: Please stop,” wrote creative digital director Sally Singer. “Find another business. You are heralding the death of style.” Vogue Runway director Nicole Phelps piled on: “It’s not just sad for the women who preen for the cameras in borrowed clothes, it’s distressing, as well, to watch so many brands participate.” chief critic Sarah Mower added that it’s “horrible, but most of all, pathetic for these girls,” and fashion news editor Alessandra Codinha completed the assault: “People will wise up to how particularly gross the whole practice of paid appearances and borrowed outfits looks. Looking for style among a bought-and-paid-for front row is like going to a strip club looking for romance.”
Established street style stars quickly jumped to point out the hypocrisy. In tweets and Instagram posts, bloggers Susie Bubble, Bryanboy, PeaceLoveShea, and Sea of Shoes reminded readers that getting photographed for street style is typically more transparent — and arguably more honest — than the undercover editorial inclusion practiced by fashion magazines. “I would think that an institution such as Vogue would respect young entrepreneurs instead of belittling them,” PeaceLoveShea wrote on Instagram.
Photographed by Cris Fragkou
An image of Whittington, captured earlier in the day by street style photographer Chris Fragkou.
Crouched beside that trashcan, watching Whittington walk across the street for the cameras is a surreal lesson in differences. We both have two legs, are both wearing designer clothes, and yet one of us looks like she was raised by RuPaul and the other one by Jar Jar Binks. While most humans struggle with taking photos of ourselves, even in selfie mode (even with filters!), Whittington has mastered the art of looking calculatedly candid. Every photo is a good photo. Every angle makes clothes look like fashion. If getting your photo taken is a sport, Whittington is an MVP. It might not be a talent that many people would consider to be an important one, but Whittington makes it look impressive.
I ask her what she thinks about the criticisms of how street style has become commodified. “You mean the Vogue article? That made my blood boil. It’s like the pot calling the kettle black. Why is it that Kendall Jenner is on the cover of Vogue in Estée Lauder makeup when she’s also in their campaign, and that ad is throughout the magazine? This idea that we should apologize for the money that we earn is stupid. I built something from nothing. There’s this idea that we don’t deserve it. It’s not fair. Do people question when athletes get sponsorships and faces on boxes of cereals? It’s the same thing.”
“When we look back on this time in 20 years, we’re going to remember this time as a beautiful thing,” Whittington reflects. “The ideas that people have with style and self-expression — why is that bad? I think this whole scene is exciting and gorgeous. They’re birds of paradise.”
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