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

(And their number one fan, Bill Belichick.)
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Just another day at the office for Kat and Ashley Hess, Boston’s emerging style influencers. / Photograph by Toan Trinh, hair by Yojanse Jimenez/Team, makeup by Laura Dillon, technical assistance by Emily Sotomayor

As kids, Kat—Katie, then—and Ashley were drawn to all things fashion. They pored over issues of Teen Vogue and Cosmo Girl, and asked for cameras for their birthday, an interest inherited from their dad, an avid hobby photographer now living in Georgia. They had similar, but not the same, interests, a natural yin-yang way of making their way through the world. Ashley was good at science and competed in pageants—she was first runner-up in Miss Teen Arkansas—where she learned many of the makeup tricks she and her sister use today. Kat, meanwhile, loved to write, and spent hours making mini magazines. “I would fold my notebook papers into quarters, staple them, and then cut them off so that it was like a little book of fashion design,” she says. “My mom still has them somewhere. I think I did that until it probably wasn’t cool anymore, up till sixth and seventh grade.”

“Yeah,” Ashley says, “our friends were like, ‘You should stop.’”

For a long time, they tried to distinguish themselves as individuals. They’d get mad when people lumped them together, even though they wore their hair the same way and shared a best friend. The worst was when people called them “the Hess twins,” Kat says. “In our minds we were two separate people.”

“This would be happening as we’re wearing matching clothes, mind you,” Ashley says.

The girls got their first taste of what it meant to earn a living in the fashion business at age 13, when Holliday moved the family from Arkansas to Jupiter, Florida, to open a clothing store called Blue Indigo. “I used to go to market in New York and Atlanta to purchase for my boutique, and the girls asked to go with me one spring,” Holliday remembers. “I gave them a budget. The challenge was to find a product within their budget that they could market and sell in the store, and the reward would be their profit.” Kat and Ashley did their research and set up shop. “I’m sure they’d flinch at them now,” Holliday says, “but the girls ended up picking out these accessories made with bottle caps. Now, this was about 2005, so their choice was trendy at the time. They chose a place in the store to display and sell their product and priced it appropriately so as to yield a profit—which they did at 13 years old!”

In 2007, Holliday met Belichick at a Florida nightclub. Neither she nor her daughters had ever heard of him. Even though the sisters considered themselves football fans, growing up in the South they rooted for Louisiana State University and mostly watched college ball. “When they first started dating,” says Kat, aware of how naive she now sounds, “we would go out to restaurants here in Boston and people would mob him. We were like, ‘Bill’s great, but why does everyone love him so much?’”

By then, the girls had already begun dreaming of a life beyond the sun and the beach. “The thing about Florida is you’re already in paradise, so a lot of kids don’t really feel inspired to work hard,” says Ashley, who insists she and her sister were always the “nerds” of their class. “It’s a beautiful life, but it wasn’t for me.” So they applied, and were accepted, to several northeastern private schools, ultimately settling on Phillips Academy in Andover, Bill’s alma mater (coincidentally, they say). By the end of their sophomore year, Holliday had also moved north.

While “nerdy” is hard to imagine—they display not a bit of social awkwardness—Kat and Ashley are certainly driven and ambitious. Holliday says that’s always been the case. The sisters considered going to different colleges, but in the end, both were recruited to play lacrosse at Trinity and decided to attend. After whirlwind summer internships in New York and L.A., though, they soon found the notoriously preppy campus stifling. Everyone was the same socioeconomically, geographically. The boys were jocks; the girls wore Ralph Lauren and riding boots. They grew bored and started getting into sneaker culture and dressing down—sweatshirts, T-shirts, lots of denim. They liked how the edginess of streetwear played off their more feminine faces and figures. They wanted to be taken seriously. They didn’t want to be cute.

The idea for a style blog came about during their junior-year semester abroad in Paris, where they found that the chicest girls wore sneakers, all the time. When the twins returned to Trinity in the fall, Kat was sporting a new pair of Adidas Superstars, white with black stripes. Then Ashley got a pair. “Nobody else at school was wearing them yet,” Kat says. “They were still wearing Converse, and we got made fun of. And I’m not even kidding, within the next two months every girl at Trinity was wearing Adidas Superstars.”

They kept their blog running throughout the school year, getting creative with clothes they owned or borrowed from friends. For the first time, they began to embrace their twinness, understanding that the very thing that might have made it difficult for people to see them as individuals in fact made them pretty unique as a team. They could make a statement without even trying.

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Instagram photos courtesy of @TheHessTwins

That August after graduation, the sisters presented their mom and Bill with a plan. They’d been looking for fashion and magazine jobs in New York, but none seemed very appealing. What they really loved, even if it hardly felt like work, was writing, styling, and taking pictures for the blog. It didn’t have to be forever, but it could be viable for now, and came with serious earning potential. The average celebrity—as in, not even a Kardashian—can command up to $75,000 for a single sponsored photo posted to Instagram. Someone you’ve never heard of with a few hundred thousand followers might get $5,000 to $15,000. Magazines certainly weren’t going to pay them that much, Ashley says, so “we agreed, if we could turn over a profit in a year—anything—they would let us continue the blog full-time. And if not, we’d reevaluate, look for a job, and get over ourselves.”

Holliday had concerns but says Belichick was actually more supportive of the idea. “I grew up believing that you go to college and then you go out and get a 9-to-5 job,” she says. “I had a large learning curve when I initially tried to understand what they were doing. [Bill] said to them, ‘If you do what you love, the money will come.’”

 

With an interest in fashion and names like Kat and Ashley, comparisons to the Olsen twins (Mary-Kate and Ashley) are all but inevitable. To a lesser extent, the Kardashians also come to mind. And in many ways, the comparisons would be apt: Like those famous families, the Hess sisters want to reach as many people as possible to grow their brand, and they’re deeply serious about business.

A typical day for the twins might go something like this: Wake up around 8:30 or 9 at the apartment they share in the Seaport. As in business, they agree to divvy up household responsibilities, and if they disagree, which they rarely do, they don’t let too much time pass without talking about it. Work emails and Instagram research until noon; photo shoot around 1 or 2, because that’s when the light is best. Between 3 and 6 they might hit the gym. They say they put 50 to 60 hours a week into the Hess Twins site, six or so hours a day of that researching trends and brands on Instagram alone. While the blog is what they feel gives them credibility—proof they have something to say—Instagram is a better measure of reach. As such, it’s where most influencers tend to make their money.