The Absolutely Fabulous, Likable, Shareable, and Altogether Baffling World of the Hess Twins

From the beginning, Ashley handled more of the business while Kat tended to the creative vision. Whoever was shooting chose the outfit; whoever modeled wrote the post. They wouldn’t identify who was who, deliberately melding into a single identity; twin is their brand. At first, as the Hess Twins 1.0, they followed a well-established “lifestyle influencer” formula: “pretty outfit, flower pic, inspirational quote, outfit, flowers, and so on,” Ashley says.

Their first paying gig came about nine months in, when the company Coach approached them to post about bags and shoes in an effort to drive more shoppers to its Boston stores. Slowly, the twins’ plan was working—they were making money—but something felt wrong: They didn’t actually buy the peonies they Instagrammed, they didn’t like wearing the girly skirts they featured, and they couldn’t spend all day in the heels they were shooting. “Once we analyzed what we were doing, we were like, ‘This is really inauthentic,’” Kat says. “Everyone is doing the same thing; every blog looks the same. We didn’t want to be that way.”

Last fall, Kat and Ashley decided to rebrand. They’d taken some time off from creating new content while Ashley underwent and recovered from back surgery. “We kind of swam up to the surface, looked back down, and thought, this isn’t us,” Kat says. “Especially after having been on such an unconventional career path for the past year, we suddenly wondered why we were trying to be so calculated and conventional.”

They also had started to resent being described as “cute,” which they both say had become inevitable for blond, petite twins living in Boston. They can’t—or won’t—say why “cute” became such a problem, though it’s easy to infer they just found it juvenile. When asked if the father figures in their life ever flinch (silently or otherwise) at some of the more provocative photos they post—visible nipples, butt cleavage—Ashley says, “We’re gonna do what we’re gonna do. I’m a strong, feminine woman, and I’m gonna wear what I want to wear.”

“Sometimes my mom asks if we can cut back on the edginess,” Kat pipes in. “She doesn’t like it when she thinks we look goth. She’s like, what happened to my darling girls?”

Of course, in influencer terms, they’re just starting out: The Hess Twins have in the neighborhood of 12,700 followers, which is just enough to be monetizable (their mom, by comparison, is pushing 30,000 followers). But it’s a number that’s growing rapidly—double, they say, since their style took an edgier turn in late fall. As a result, they’ve been able to assemble a healthy roster of local and national clients, including Equinox, Jugos, Concepts, and AllSaints, for whom they work for cash and trade: gym memberships, beauty products, free clothes, photo rights.

Businesses that have collaborated with them have responded to their voice and their ability to get people to pay attention—and even to think and dress differently. “They fit a cool, new-energy vibe that sort of hit the nail on the head for us,” says Riccardi’s Dallai, who first noticed the twins on Instagram and thought they’d be good ambassadors for his edgier women’s wear. “It’s important to us to flex our Boston muscle and showcase the youth movement here. There’s no mystery in fashion anymore.”

Most recently, Kat and Ashley shot a New Balance campaign for the Concepts sneaker store in Harvard Square, a project designed to show female shoppers how to wear men’s styles with confidence. “The idea was to show women it’s okay to wear things differently,” says Concepts co-owner Deon Point. “Some of these brands do a pink shoe, and that’s what the female shopper gets. I think women are over that.” While Point says he doesn’t know that he trusts bloggers in general—“A lot of opinions can be bought,” he says—he liked the twins’ overall look and feel. “We don’t typically approach people on social media,” he says, “but we had mutual friends and I like their style.”

So far, Point says, Boston bloggers aren’t necessarily influencing retail sales, but their existence does help shift the city’s image—if only because people outside Boston can see there’s more to fashion here than cashmere and pearls. Kat and Ashley suspect they reach as many national and international followers as local followers, with an even split between men and women, their audience ranging in age from late teens to early fifties. As for being influencers, though, the twins aren’t afraid to start close to home. “You’d be surprised by how many of my mom’s friends have asked me where to get the Supreme T-shirt that one of us wore to a Patriots game,” Ashley tells me. “It was an awesome moment!”

The weather is no better by early March when I find Kat and Ashley staging a shoot in a cement park next to the Boston Convention & Exhibition Center. Ashley is wearing a white cutout ribbed tank, aqua-blue sweatpants rolled up twice at the waist, and white leather high-tops. Kat is behind the camera. They live nearby in the Seaport at least partly because the neighborhood suits the aesthetic of their blog. “It’s new, shiny,” Kat says. “There’s a lot of glass, some brick, so that works. There’s pretty shadow play.”

For now, being different and defying expectations is the whole agenda—and that includes giving off the perception that, in oversize sweatpants and $100 white ribbed T-shirts, they’re not trying too hard. “We’re going to wear what we want to wear…with no regard to meeting or conforming to people’s expectations of Boston,” Ashley says. “We don’t see this as a disadvantage, though. We see our alternative fashion as the opportunity to stand out among the blogs here that, mostly adhering to the expectation of preppy clothing, end up looking very similar.”

In contrast to the effortless cool they project, and true to Boston sensibility, Kat and Ashley work hard. They’re not big drinkers; hangovers, they say, are not their style. Instead, they’re very serious about being taken seriously. And while it’s tempting to want to think there must be something better that smart women can do with their lives than become Instagram stars, the truth is that only smart women can turn this sort of thing into a living—which they’re well on their way to doing. “Like every designer, I love a well-styled, beautiful photo, but honestly my favorite part about the Hess Twins is what they say,” says jewelry designer April Soderstrom, who has hired them on occasion. “Witty women in fashion are always welcome in my book, and I’m always guaranteed to get a giggle out of their captions.”

At the same time, Kat and Ashley are quick to reassure me that they’re not haters and have no problem whatsoever with the preppy look, or however it is you want to dress. “Our goal is not to tell people what to wear,” they email at one point, in a joint statement. “It’s, in fact, the opposite. We want to inspire people to embrace their own sense of style, exactly like we do, and leave the house feeling confident and satisfied in what they’re wearing.” Mainly, though, they hope to inspire people in Boston to think about what they wear and what it means to them, beyond what they might see around them every day. “When it comes to style in Boston, we’re not here to say that the traditional and preppy one typically associated with it is wrong,” they insist. “We’re just here to demonstrate that there’s an alternative. There’s a different way to live and dress here other than what people assume or expect, and you can find that in us.”

In addition to overhauling their Instagram presence, the twins are launching a new website as part of their rebrand. This site, they say, aims to position them as “creators and consultants,” and, ideally, serve as a launch pad to something bigger. Maybe it’s creative direction for brands. Maybe it’s styling, together or apart from each other. Maybe it’s a position at a magazine, and they’ve already applied for those—as a pair, of course.

Leaving all doors open is part of their millennial charm, and they’ll do this until it’s no longer fulfilling or one or both of them want to move on. They’ve thought about moving the Hess Twins brand to New York, but they quite like Boston’s big fish, small pond potential, especially the tight sneakerhead and streetwear community they’ve joined. As millennials constantly remind us, not every career needs longevity in order to be valid.

And so for now, Kat and Ashley will continue to blast out photos of themselves, highlight their taste in music (lots of hip-hop), recommend some of their favorite Boston hangouts, and give insight into their travels around the world, with the Patriots and with each other, in hopes of getting you to join their growing cast of followers.

“We don’t want to be just Instagram models,” Ashley says. “So many people these days are Instagram models, and it’s like, but what is your viewpoint on life? What are you about? What are your interests? And it’s like, I have no idea by looking at these girls who all look the same.”