Inside the Monogrammed, Monetized World of New York City's Preppy Bloggers

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And yet, their blogs—often patterned in shades of pink and green and touting monogram logos—are thriving like a Vineyard Vines boutique in Palm Beach. These girls aren’t reinventing the wheel here, style-wise. On any given day, they’re dressed like Kate Middleton and waxing poetic about their waxed-cotton Barbour jackets. But they’ve managed to make a name for themselves, both on the internet and, improbably, in New York City.

Perhaps the most well-known of the bunch is Carly Heitlinger (left), a 25-year-old Tampa native who created The College Prepster her first year at Georgetown University. "I started my blog out of desperation," she said. "I was barely passing my classes and I was having a difficult transition in college. As luck would have it, I loved it, stuck with it, and then social media became a ‘thing.’ While I continued through college, the industry continued to evolve. At one point, I realized that I could probably use my blog as a talking point or a bullet on my resume to get a job."

That was seven years ago. She’s since graduated with a degree in marketing, moved to Manhattan, landed (and left) a 9-to-5 gig at a start-up, and made the site a full-time career. Back in 2008, Carly wore a lot of critter-motif J. Crew chinos (this was, of course, when J. Crew was still making critter-motif chinos) and idolized Blair Waldorf. And although she’s gone from an undergrad in D.C. to a working girl in NYC, her site hasn’t changed a whole lot, and neither has her style—which is part of the reason she’s been able to build such a big audience and, in turn, a big business.

"A couple of years in, I realized I could make money from blogging. It was very slow at the beginning and even when it picked up a bit, I still assumed it would be a nice supplemental income," she said. "At one point, my blogging income was twice as much as my salary was, even though I was only spending about four hours after work on it."

Heitlinger still wears a lot of Lilly Pulitzer and L.L. Bean—except now, instead of spending all her allowance on clothing, it’s often gifted straight from the brands.  There are times an entire outfit is, in blogspeak, "c/o," which is something sites are legally obligated to disclose. The rules on social media are a little more ambiguous, and it’s often impossible to know whether a pair of Kate Spade flats has been deemed Instagram-worthy because they’re simply pretty or because they’re pretty profitable, too.

Financials aside, it’s clear that she only endorses brands that fit her aesthetic, and those brands tend to be high-profile. In the last few months alone, Heitlinger has worked with Jack Rogers, Lilly Pulitzer, and Kate Spade. At this point, labels are even scrambling to dress her boyfriend, a handsome frat boy type named Garrett McCarthy who makes frequent appearances on The College Prepster. Last month, he accompanied Heitlinger to a Vineyard Vines store opening, decked out head-to-toe in the brand. A few days earlier, the twosome posed in matching penny loafers courtesy of Nordstrom.

There’s a reason why big-name designers are competing to get their clothing in her closet—and, in turn, on her site. Though she doesn’t publicly reveal traffic figures, Heitlinger has more than 122,000 fervid Instagram followers (who provide an endless scroll of "Can I just be you?!" comments). She also has nearly 30,000 fans on Twitter and Facebook each. Her blog may be niche, but her audience is large and, more importantly, fiercely loyal.

Interestingly, one of Heitlinger’s best friends is also one of her biggest competitors. The Serena to Carly’s Blair, Jessica Sturdy (left) has glossy blonde ringlets and a blog called Bows & Sequins. She’s a self-professed rosé enthusiast and SoulCycle addict who’s rarely seen without nautical stripes and red lipstick. She has half the amount of Instagram followers as Carly, but 60K is plenty impressive—at least judging from the number of brands she regularly partners with.

Sturdy started a fashion blog during her senior year at the University of Illinois after realizing she wanted to pursue a career in fashion instead of going to law school as planned. This was right around the time J. Crew staged a revamp and Jenna Lyons went from a corporate executive to a Noted Fashion Person. "Preppy became trendy, and I’d always gravitated towards that," she said. "My family never vacationed on the East Coast or anything like that, but I always had a strong affinity for the East Coast aesthetic."

After spending a few years in Chicago, she in fact ended up on the East Coast—though you probably wouldn’t be able to tell with a glance inside her closet. "I live in the East Village and I get a lot of looks like, ‘Is she lost…?" she said, referencing her wardrobe that’s heavy on plaid, patterned turtlenecks, and hot pink. "But my style has a little more of a mix now that I’ve been in downtown New York for a few years."

Unlike Heitlinger, Sturdy has a full-time job working for a jewelry company where, among other things, she manages blogger relations. This has given her an advantage when it comes to negotiating with brands for her own blog, especially since, unlike many bloggers, she doesn’t have a manager or agent on her payroll. A lot of her internet pals have hired agencies like Digital Brand Architects, and while she does see the benefits, she prefers handling the business nitty-gritty herself. "I go back and forth," she said. "My parents are entrepreneurs. Money talks can be uncomfortable, but I like to have full control."

That’s not to say running a business hasn’t been without its challenges. "It crossed the line of being a hobby, and as my traffic grew, the affiliate commission started to grow. Then brands would reach out and ask, "How much do you charge for this?’ And I’d have no idea." She’s gotten the hang of things, but keeping her side hustle going requires a lot of work—and a lot of time. "The dark circles under my eyes are real. I know there’s an expiration date, I just don’t know when," she said.

At this point, she could probably ditch the career and take up blogging as a job, but it’s not something she’s seriously considered. "Pinterest just took away affiliate links," she said. "That’s why I’ve been so hesitant to become a full-time blogger. Things can change. There’s no guaranteed longevity."

Another College Prepster pal and a fellow force in preppy personal-style blogs is Mackenzie Horan (right). Similar to Heitlinger, Horan started Design Darling during a rare bout of boredom as a student at Bucknell. Now 25, she’s turned her site into a lucrative e-commerce business that sells $395 hand-painted vases, gold-foil prints, and lots and lots of monograms. "I never imagined that blogging would become such a viable career path for me but I'm certainly thankful that it has," she said. She’s been doing it for five years, much longer than most millennials have stuck with a single job. "The fact that I get to do that for a living never gets old."

Heitlinger, Sturdy, and Horan are just a handful of the preppy bloggers valiantly keeping cable knit relevant. After poking around Instagram and Twitter it becomes apparent that these girls’ biggest followers—the ones who post fangirl comments and tweets—are just like them: Pretty and preppy, and more often than not, penning rookie lifestyle blogs with twee alliterative names like Rainboots & Retail, Preppy Panache, and The New Naples.

Heitlinger fields lots of emails from girls who have big dreams of moving to the Big Apple, as well as, unexpectedly enough, parents. "About one in three ‘fan’ emails I get is from a mom who reads my blog. She might have a daughter in high school who introduced The College Prepster to her or she has daughter my age and feels like reading my blog gives her insight into her daughter's life, or she has boys and thinks of The College Prepster as a daughter she never had."

Sturdy has found that, in addition to the usual suspects (an abundance of "college girls who aspire to live in the city one day"), she also has a steady audience of young moms with a husband, a house, and maybe a kid or two…and probably not a country club membership. "There’s a lot of thirtysomethings who have moved out to the suburbs and are living a little vicariously [through me]." You certainly can’t blame them.

Lisa Birnbach, the author of 1980’s The Official Preppy Handbook and an icon of sorts among girls who wear fisherman sweaters, didn’t know this subset of bloggers existed until she began researching True Prep, her 2010 sequel. "I was already halfway through the book. It was coming out later that year, and I became aware of theses websites—‘Gimlets and G&Ts,’ ‘Manicures and Pearls,’ some with prep in the name, others with gingham and grosgrain. Some were Southern, some were sororities, some were girls who just really loved Lilly Pulitzer," she said. "I was going to list them in the book, but I become so overwhelmed. It would have taken up the whole book!"

The preppy ethos Birnbach preaches in her bestselling style manual is in sharp contrast to the very purpose of fashion blogging, which is, at its most basic, photographing yourself in shiny new outfits. "To be truly prep, you're reviving your mother's old jacket, you’re wearing your dad's old tennis sweater, you’re borrowing those corduroys from your roommate. Where they come from—the pedigree—is not important, " said Birnbach. "Being able to recite the designer you're wearing, even if you're the very best friend of Tory Burch or Trina Turk, that's showing off."

Of course, when showing off a brand is the very thing that’s bringing in paychecks, old-fashioned preppy principles tend to go out the window. Maybe the moneyed WASPs of the ‘80s didn’t advertise where their clothes came from, but the moneyed WASPs of the ‘80s didn’t have fashion blogs. Birnbach acknowledges that now is a much different time.

"I had a talk in Houston, and everyone wore pink and green. I showed up in khaki and navy and I felt like I let them down," she said. "I respect these preppy bloggers, but we're doing different things. The fact that they’re making money is great."

Brand endorsements aren’t the only way bloggers pull in money. Sidebar ads and partnerships with companies like RewardStyle and LiketoKnow.It can earn top bloggers six-figure paychecks. But working with respected labels gives fledgling bloggers legitimacy in a very crowded space—as long as they’re not working with every company that comes their way.

"If it's not a brand I wear in real life, you're not going to see it on my blog," said Horan. "I'm lucky to get to work with companies like Kate Spade, Nordstrom, Cynthia Rowley, Lilly Pulitzer—names I really respect and feel are in keeping with the classic aesthetic I know and love." Preppy bloggers tend to be proud of their association with brands, but brands remain a little more coy about things.

When Racked reached out to Lilly Pulitzer to learn more about their partnerships with preppy bloggers, Jane Schoenborn, Vice President of Marketing and Creative Communications, offered up this sound bite: "We are thrilled that bloggers relate to what we do and use our product to tell their personal fashion stories. While we do not call ourselves ‘prep’ and consider ourselves a lifestyle brand born out of the needs of the sunnier days in life and travel, we love it when people take our unique style and make it their own. Lilly has always been a word of mouth kind of brand, and digital influencers are the best form of word-of-mouth meets technology."

Similarly, a spokesperson for Kate Spade said, "At this time, we will decline to comment on this piece."

Lindsey Worster, VP of Brand Communications at Vineyard Vines, was a bit more enthusiastic. "We have opted to engage specific influencers that have already expressed a love for our brand," she said. "Rather than seek out adjacent influencers with high numbers of followers, we're fostering genuine brand advocacy. It's almost serendipitous that we've seen so many preppy bloggers become popular in recent years."

Regardless, the relationship between brand and blogger is a mutually beneficial one. Many of these clothing companies have been around for almost a century, but try as they might, it isn’t easy for brands once beloved by your grandparents to stay relevant. (But boy do they try…remember when Sperry introduced hot pink sequin boat shoes last season?) It’s a no-brainer for storied labels to align with bloggers who take professional-quality photos of their adorable terriers, elaborate brunches, and, if the incentive is right, of themselves in a head-to-toe look. It can be cheaper than an advertising campaign, and a whole lot more profitable.

You won’t see seashell-print Lilly Pulitzer sundresses and Vineyard Vines plaid pants marching down Bedford Avenue—or on the cover of Vogue—anytime soon, but Heitlinger and crew don’t seem to mind, and neither do their combined millions of followers. Besides, they tend to hang out uptown.