“To be perfectly honest with you, I needed a few Americans to tell me what it means to win this award,” said David Fischer, the founder of the company Highsnobiety.

Mr. Fischer was sitting in an airport in Spain, wearing a denim jacket and a designer baseball cap. About 10 days earlier, in New York City, Highsnobiety won a National Magazine Award for general excellence — its first nomination and win at the Oscars of the magazine world.

“I’m not a journalist by background, nor would I consider myself a great writer,” Mr. Fischer, 41, who lives in Berlin, said.

He started Highsnobiety as a sneaker blog in 2005. Today it is a website that covers fashion and youth culture broadly. It is also a clothing store and clothing line and, more lucratively, a creative consultancy and production agency. In other words, Highsnobiety writes about and recommends T-shirts, but it also makes its own T-shirts, sells and advertises other labels’ T-shirts, advises brands on how to market their T-shirts and throws big parties in honor of T-shirts.

But is Highsnobiety a media company? “It’s certainly not a clear yes,” Mr. Fischer said. “I was mostly interested in finding exciting new things and putting those things in front of the audience. And I suppose I was always excited about building a brand, more than anything.”

The magazine is printed twice a year. Its stories and images are frenetic, meant to speak to readers who are either young and cool or interested in being young and cool. The editor in chief is Willa Bennett, who ran social media at GQ magazine until 2022.

On the April night she accepted Highsnobiety’s National Magazine Award, her former boss, the GQ editor Will Welch, was “hooting and hollering” (his words) for the 30-year-old woman. She wore a gray Thom Browne suit with a matching skirt layered over the pants, and black Tabi cleft-toe shoes. She spoke into a microphone about how magazines are important and how print media matters.

Neither is a given in the current media landscape. About six months ago, Condé Nast announced it would cut five percent of its work force, following some years of turmoil and nine-figure annual losses. Hearst Magazines announced layoffs in 2023. So did, for that matter, Highsnobiety.

And yet people are still making magazines. Nylon returned to print this month; last month, the new owners of Complex magazine and Life magazine announced print resuscitations. In New York, new indie titles like Family Style and Byline have emerged.

Ms. Bennett is idealistic about this future. She is generally cheerful, prone to skipping down sidewalks, even while wearing a smirk that borrows more from Daria than Mary Tyler Moore. She is also uncommonly curious about people — especially young people, whose ideas and skills she mines for the magazine.

“I believe it’s my responsibility to, like, make sure that young people still dream of being journalists,” she said. “We just need to keep iterating and continuing to stretch what it means.”

Suiting Up

Ms. Bennett is known to wear a suit and tie to work most days, not unlike the workers surrounding her in Manhattan’s financial district.

Highsnobiety’s offices rise 11 floors above the Charging Bull sculpture. On one wall, the words “Virgil was here” are scrawled beneath the company’s logo. The designer Virgil Abloh shared many of the same interests as Highsnobiety: adolescence, corporate collaborations, the blurring of high-end fashion and “streetwear.”

Ms. Bennett’s cube-shaped office houses various gifts. She has an action figure of the rapper ASAP Rocky, dressed in an outfit from his Highsnobiety photo shoot. She has a skateboard and a basketball hoop, though she neither skates nor hoops. There is a framed thank-you note from Donatella Versace and a receipt for $19,010 from the Château Marmont in Hollywood, where Highsnobiety co-hosted a dinner before the Grammys in February.

Inside a conference room named after the famous Berlin nightclub Berghain, Ms. Bennett hosts regular brainstorming sessions. It is here, for example, that she was inspired to pursue a cover story on Dries Van Noten, the 65-year-old Belgian designer who recently announced his retirement.

“We were all talking about how Dries is the best,” she said. “This consistent designer that young people can always trust.”

The spring issue had three cover stars: Mr. Van Noten, the musician Andre 3000 (age 48) and the model-actress Pamela Anderson (age 56), none of whom seem like intuitive choices for a magazine that typically concerns itself with young emerging talent. The previous three cover stars were the rapper Lil Yachty (26), the TikToker Khaby Lame (24) — a story Ms. Bennett assigned to a fellow TikToker, whom she later realized was still a sophomore at New York University — and the model Grace Valentine (23).

Still, even if the subjects were older, Highsnobiety’s approach to them was not. “Pamela Anderson Is Mother,” one headline read. Ms. Anderson was a more personal choice for Ms. Bennett, who wrote in the issue that Ms. Anderson’s 1989 Playboy cover once hung on her bedroom wall.

On that cover, Ms. Anderson wore a blazer and tie and nothing else. She wore a blazer and tie on her Highsnobiety cover, too. Women are often styled in men’s wear in the magazine’s pages. Squint a little and Billie Eilish, the first cover star chosen by Ms. Bennett, bears a resemblance to the editor — the bare face, the dark hair with a middle part, the head tilted slightly downward. She looks as if she’s glaring at you, but really it’s more like she’s taking the measure of you.

Ms. Bennett also studies people, more comfortable asking questions than answering them. (How was your day? What are your favorite brands? Do you like writing?) Standing outside Cubbyhole, a West Village lesbian bar, she would only point vaguely in a direction when asked where in the neighborhood she lived with her partner, a television writer.

The personal details she was willing to part with were these: Ms. Bennett grew up in the Silver Lake neighborhood of Los Angeles and attended the private school Oakwood. Her parents were divorced. She lived with her mother, a therapist who moved to Hawaii when she was in college. Her father, a prominent music manager, lived in Nashville for most of her life. She wears his birth year, 1950, on a silver ring.

Ms. Bennett came out when she was a teenager, she said, in the comments section of the Australian pop star Troye Sivan’s coming-out YouTube video — an anecdote she later shared with Mr. Sivan while they were seated next to each other at a Prada runway show.

She had always wanted to be a writer. “At the time, ‘Twilight’ was huge,” Ms. Bennett said. “I was like, I’m going to write the gay ‘Twilight.’”

But she was also drawn from a young age to the power of magazine covers — not only Ms. Anderson on Playboy, but also Cory Kennedy on Nylon and Megan Fox on GQ. “What does it mean for a men’s magazine to have someone like Megan Fox on the cover?” she said.

A onetime ballerina, Ms. Bennett attended Sarah Lawrence College on a dance scholarship. When she told her adviser she wanted to write for magazines, the adviser suggested she write her thesis about the future of the industry. Instead Ms. Bennett pitched embedding in a middle school for four weeks, writing “about what teens are reading and how they’re reading it,” she said. The project helped her land a job after graduation at Seventeen.

“She really is a voice of and a champion of what young people care about,” Mr. Welch, the GQ editor, said. “And what young people care about isn’t exclusively, necessarily, all young subjects.”

Ms. Bennett, for example, doesn’t seem to hang out at bars or restaurants catering to the city’s cool 20-somethings. She spends her time at established fashion and media haunts, like Via Carota or Minetta Tavern or the Odeon. One recent Thursday night, walking into the Odeon in TriBeCa, she immediately recognized a few young editors sitting at a table outside the restaurant.

She used to work with them at GQ, she explained, bouncing over to the table to say hello. “They said they all work at Vogue now,” Ms. Bennett reported when she returned.

‘Larger Than Life’

By the end of 2005, Mr. Fischer was fielding brand requests to advertise on his sneaker blog. By 2010, those advertisements had shifted to sponsored content — or brands paying Highsnobiety to write positive pieces.

Over time, Mr. Fischer said, he realized branded stories “performed best if we shot our own imagery, too,” rather than republishing photos from the companies. This is how Highsnobiety gradually became “more like a full service creative agency, rather than just being a publisher.” Brands began asking Highsnobiety to host events, like pop-ups or parties related to the content Mr. Fischer’s team was producing.

“We always kept it very connected to our editorial,” he said.

Many companies that produce journalism have strict church-and-state divisions between editorial and advertising efforts. The division at Highsnobiety is more like “God and church,” said Nichelle Sanders, the general manager of Highsnobiety in the United States.

The journalism “inspires us in the commercial efforts that we create,” said Ms. Sanders, who also oversees Highsnobiety’s research papers of consumer insights into its audience. “The reason our clients come to us is because we can get into the brain of this amazing editorial team.”

Those clients include Champion, best known for its sweatsuits, when it’s looking to reach cooler, younger shoppers. Voilà, suddenly Champion and Highsnobiety are hosting a rave together during London Fashion Week, partnering with an edgy local radio station. (Highsnobiety once collaborated on a T-shirt with The New York Times, one of many products created for an event series celebrating New York.)

Mr. Fischer does not worry about his audience being skeptical of these paid partnerships.

“I think people have accepted that brands like Highsnobiety and influencers need to make a living,” he said. While it is an open secret in fashion media that some magazine covers and features can be bought outright by advertisers, with no disclosure to readers, Highsnobiety denies engaging in that kind of pay-for-play.

“They can go through the sales side, and they can buy branded content,” Ms. Bennett said. “They cannot buy a magazine cover.”

Although the company declined to provide specific financial figures, it is profitable, according to Juergen Hopfgartner, the president and chief operating officer. Its e-commerce business is also growing, aided by the resources of Zalando, an online German retailer that paid 123.6 million euros (about $131 million) to acquire Highsnobiety in 2022. In February, Highsnobiety opened a store in Berlin that, beyond selling products, will be used as a “brand activation space” for clients, Mr. Hopfgartner said.

All things considered, it is not surprising that Mr. Fischer described his company as a “weird mishmash of these different worlds.”

Lauren Sherman, the writer of the fashion industry newsletter Line Sheet, said that Highsnobiety “doesn’t feel like it comes from journalism.”

“It feels like it comes from commerce,” she continued. “But that’s very modern.”

And that may be what is required to find success in the dire publishing landscape of 2024. But a distinct, assertive voice also helps.

In less than two years, in addition to winning the National Magazine Award, Ms. Bennett has shifted Highsnobiety’s audience from predominantly male to a 50-50 gender split, Mr. Fischer said. At GQ, Mr. Welch said, Ms. Bennett possessed a rare confidence and fearlessness, particularly for someone who was both very young and technically in charge only of the social feeds.

“She has a bit of that larger-than-life thing that a lot of the leaders in this industry are missing now,” Ms. Sherman said.

In her slouchy suits, Ms. Bennett somewhat reminds Ms. Sherman of the editors with big personalities that she grew up idolizing, like Liz Tilberis of Harper’s Bazaar or Jane Pratt of Jane.

“People who are like that just don’t go into magazine publishing anymore,” Ms. Sherman said.