Jack Carlson, founder of Rowing Blazers.

One sunny afternoon a gentleman in his late 40s walked into Rowing Blazers‘ New York pop-up on Rivington Street. He asked the brand’s founder, Jack Carlson, to join him next door for ice cream at Morgenstern’s, where he proceeded to offer Carlson unsolicited advice about his line. The man was a Princeton graduate, preppy and pleased with the brightly colored rowing blazers and rugby shirts Carlson designed, but didn’t like the T-shirts he created with Joe’s Pizza.

“He said something like, ‘They have no place in the brand,'” recalled Carlson, who is 31. “I was polite, but in my mind I was thinking it’s my brand and if I think it’s cool, then it makes sense. There are people who don’t quite get it, but you never hear any of these comments from younger people.”

Carlson, who started Rowing Blazers in 2017, can easily be described as preppy. He grew up in Boston and London, attended Georgetown University, studied archaeology at Oxford University and was on the U.S. rowing team. But he stays away from using what he calls the “p” word in relation to his line because of its connotations, which Carlson believes are stuffy and dated. With his collection, which he created after putting together a book, also titled “Rowing Blazers,” which documented rowing blazers from around the world, Carlson wanted to reenergize preppy staples in an authentic, relevant way and present them on a variety of models who don’t all look like they grew up on Nantucket.

He’s become the collaborator of choice for heritage brands such as J. Crew and Sperry that are trying to reach a customer who’s no longer impressed with the preppy lifestyle and entranced with streetwear or ath-leisure — Carlson doesn’t categorize Rowing Blazers as streetwear, but it has influenced the line and the brands he works with, such as Eric Emanuel and Death to Tennis, which is selling out of a rotating space in Rowing Blazers’ Grand Street store.

Companies associated with preppy aren’t melding references in the same interesting way that Carlson is, but they are acquiescing to the cultural climate. Tretorn tapped André 3000 to design capsule collections and Nautica named Lil Yachty a creative designer. Ralph Lauren looked to its archives to rerelease its Snow Beach and 1992 Stadium collections that were made popular by the Lo Lifes, a Brooklyn-based group of Ralph Lauren collectors. And others are making more pronounced efforts to position preppy in a less constricting, prescriptive way, including, in women’s wear, Tommy Hilfiger, who for three seasons has linked with Gigi Hadid for a collection and who, in September, will link with Formula One driver Lewis Hamilton for a men’s wear collaboration.

“Preppy style can still be relevant, but the lifestyle associated with it needs to evolve so it’s not this pure symbol of wealth that it used to be,” said Brendon Babenzien, who grew up in Long Island and filters preppy through a street, skate and punk lens for his line Noah. “I think the message of what is aspirational has changed. It seems that it’s aspirational now to just be happy or to do the right thing. I can’t imagine just selling people on the idea that success is defined entirely by your clothes or your house or car or whatever.”

Sperry, which has partnered with Noah on product, addressed this cultural shift, titling its spring/summer 2018 campaign “Prep for All.” In a press release, the 83-year-old boat shoe company stated: “Sperry is seizing the opportunity to shift past beliefs around the perception of prep and preppy style, transcending boundaries to celebrate a system of all-inclusive values. The brand is starting with an expanded view of prep that ditches the rules and embraces all individual style spins that make prep, prep.” The campaign features a colorful cast of models breaking the rules of preppydom, like driving a motorcycle instead of riding a horse or playing tennis in an abandoned pool rather than joining a private swim club.

“We aren’t denying that we are preppy, but we wanted to open the boundaries and let people know it’s OK to interpret preppy in your own individual way,” said Kate Minner, Sperry’s chief marketing office. “The customer doesn’t want to be told what to do.”

Thom Browne, whose imaginative line nods to preppy but transcends it, hasn’t been as overt as Sperry in his pivot, but by placing his very specific idea of a suit on NBA players from the Cleveland Cavaliers or soccer players from the FC-Barcelona soccer club — he recently signed a three-year partnership to dress the soccer team off-court — the designer appears to be trying to normalize his miniaturized proportions, speak to more people and show them in a new context.

J. Press, a preppy stalwart, has never strayed too far from its roots, but it veered into new territory in 2012 with J. Press York Street, a line targeting younger shoppers designed by Ariel and Shimon Ovadia of Ovadia & Sons for four seasons. The company opened a J. Press York Street store on Bleecker Street in 2013, but ended its relationship with the Ovadia brothers in 2014 before shuttering the line altogether and closing the store.

The company recently brought on Robert Squillaro, who previously worked at Brooks Brothers, to streamline the brand as senior vice president and chief merchandising officer. According to Squillaro, the J. Press customer is underserved and looking for classic, American sportswear and tailored pieces that most companies have stopped making — with the exception of The Andover Shop located in Harvard Square in Boston, which is seeking new ownership, or O’Connell’s Clothing in Buffalo, N.Y.

Instead of trying to chase a wider audience — J. Press is privately held by Onward Kashiyama USA and operates three stores — the brand is getting back to the basics with a print catalogue and its flagship at the Yale Club in New York City, which Squillaro said has increased business significantly. But the company remains keen to attract a younger consumer, which it plans to do with a more fashion-forward line to make its debut this fall with slimmer fits that will accompany its classic heritage assortment. The lines will be distinguished by tag colors. Squillaro also hinted at a collaboration with a designer to be released later in the year.

“I don’t see J. Press involving streetwear into what we do,” said Squillaro. “That’s not to say we wouldn’t have an accessory that’s more street, but I don’t see us doing a rugby shirt with a giant mermaid.”

When Lisa Birnbach wrote “The Preppy Handbook,” which came out in 1980, she said it wasn’t meant to be a corrective for the tacky dressing that was happening during that time, but rather a guide to looking presentable and fitting in. And much like Sperry’s “Prep for All” campaign, Birnbach believed it was a guide for everyone. In the first line of the book she wrote: “It is the inalienable right of every man, woman and child to wear khaki. Prep is not restricted to an elite minority lucky enough to attend prestigious private schools just because an ancestor or two happened to arrive here on the Mayflower.”

Birnbach remembers visiting Richmond, Va., during her book tour and wondering why a delivery man wearing overalls was interested in the book. She came back a second time and he was there again, but he had tweaked his uniform.

“He was wearing overalls with a webbed belt, and I felt so proud,” said Birnbach. “Maybe I was making America better looking one webbed belt at a time.”

By 2010, when Birnbach released her follow-up “True Prep,” Ralph Lauren had established preppy advertising that was associated with aspirational and rich rather than generic and service-oriented. Brooks Brothers, which was acquired by Italian group Retail Brand Alliance from Marks & Spencer in 2001, was no longer wholly dedicated to the bastions of preppy. And Vineyard Vines presented preppy as accessible and fun with its whale logo and Easter egg hues. Preppy had been watered down, redefined and disseminated to an array of consumers to such an extent that it became more of a cliché than a style.

But preppy purists — those of them who are left and who live in the comments section of sites like Ivy Style — aren’t fond of the interpretations. Under a post on Ivy Style about the opening of Rowing Blazer’s temporary Grand Street store, one commenter, who identified himself as Christopher Hosford, stated: “Fashion aside, I am inherently prejudiced against clothing that purports to identify a wearer as a prep or university varsity athlete, when indeed he was no such a thing.…The glowering fellow with the shades and regatta patch — he probably hadn’t seen a body of water bigger than a Crown Heights mud puddle nor rowed across one — is a particularly risible example.”

“I think the purists feel left out,” said the founder of Ivy Style, Christian Chensvold, when asked about the current state of preppy apparel. “For my readers who have grown up on a brand like Brooks Brothers, they believe what’s happened to it is an utter travesty and a complete dismantling of the greatest men’s wear institution in our history.”

Lou Amendola, Brooks Brothers’ chief merchandising officer, said Brooks Brothers continues to celebrate its heritage combining tradition and innovation.

“We invented and still sell the original polo button down shirt, as well as introducing madras, seersucker, Harris tweed and other ‘preppy’ staples,” said Amendola, who added that Brooks Brothers recently relaunched its “fun shirt,” which was invented in 1970, but the brand has made it customizable.

It’s this perspective that led Frederick Castleberry to change the name of his popular men’s wear blog from Unabashedly Prep to The F.E.C. Diaries. Castleberry spent seven years as a concept designer at Ralph Lauren’s Rugby brand before starting his own made-to-measure line, F.E. Castleberry. Castleberry, whose collection is part preppy/part Wes Anderson eccentric, didn’t want to be beholden to the confines of preppy or debate with diehards over the validity of his line.

“The reason why I took a step to the side from that lane is so I wouldn’t have to do what these brands are doing,” said Castleberry. “Instead of trying to redefine what preppy was, I just stepped to the side and built my own world. It’s almost if these brands are trying to convince you to like preppy and the consumer is smart. They want to see bigger stories and connect to people. Ralph Lauren is sitting on a goldmine of designers who bled for this brand and wear it best. People want to hear stories about those individuals.”

Despite his detractors, Carlson is enjoying the community he’s created where shoppers carrying Supreme bags feel as welcome as the banker wanting to liven up his weekend wardrobe. He’s also having fun digging through brands’ archives and helping them understand that it’s not always the matter of pivoting the messaging around preppy, but having someone reassess what they’ve already created through fresh eyes. At Sperry, Carlson came across a Dad-esque sneaker the company made in the Nineties.

“When I saw the sneaker, they immediately said, ‘You don’t want to do anything with that.’ But I definitely want to do something with it,” said Carlson. “Sometimes these brands have a lot of cool in them, but they don’t necessarily realize it and everything that they are doing is going in the opposite direction.”