At Men’s Fashion Week in Milan earlier this summer, critics and influencers from around the world braved the city heat to attend the shows—from Dolce & Gabbana to Gucci, one solemn affair after another—looking sultry in black T-shirts and leather pants and smoking cigarettes.

The scene was decidedly different at the presentation for the British men’s-wear brand Dunhill, a reconstructed tea party that took place in the gardens of the 19th-century Museo Poldi Pezzoli, around the corner from the ritzy Via Montenapoleone.

Guests known for wearing alternative clothing showed up in camel-colored trousers and linen shirts—in theme with the collection, which included cable-knit sweaters, suede jackets, and blue suits. Violin players greeted the guests, who sheltered themselves from the sun with parasols, while handsome male models paraded down the catwalk looking like guests at a Gatsby party. It was, as the brand’s creative director, Simon Holloway, later put it to Women’s Wear Daily, rooted in “radical classicism.”

Holloway is leaving his mark on every element of the collection.

“Whether it’s in America, or in Asia, or in Europe, this is a version of elevated society dressing that always exists,” says Holloway, who took over the company last year. “But at the same time, it’s a space that everybody ignores, because it’s all quite sort of stuffy and traditional.”

There were no automated mannequins, larger-than-life L.E.D. screens, or riveting sound installations at the Milan presentation, yet it quickly became, as one industry veteran put it, a true “fashion moment.”

For days afterward, people raved. Wallpaper picked it for its roundup of Fashion Week highlights, while Hypebeast wrote that Holloway was “in his element.” The day after the show, The Guardian speculated on the demise of London Fashion Week. Following Brexit, brands have been leaving the U.K. en masse to escape high export taxes, with many relocating to Milan. (Dunhill’s commercial and sales teams have moved to Milan, but most of its manufacturing will remain in the U.K.)

“It was the sort of collection everyone has been waiting for,” luxury-brand consultant Isabelle Harvie-Watt says. (Full disclosure: Harvie-Watt is my mother.) “People were really like, Finally, an English men’s-wear brand which is rooted in our rich traditions.”

In Milan, Holloway revealed an unexpected approach to suiting.

There does seem to be a vacuum in England for a luxury brand that reflects the country’s deep men’s-wear tradition, and Dunhill looks poised to fill that void.

The company dates back to 1893, when Londoner Alfred Dunhill took over his father’s saddling business. Automobiles were on the rise, and Alfred decided to drop whips and make gloves, goggles, dashboards, and voltmeters instead.

At the dawn of the Jazz Age in the 1920s, Dunhill switched from goggles to tobacco, Art Deco–style pipes, and cocktail-mixing sets. Fast-forward to 1966, when Truman Capote wore a Dunhill suit for his Black and White Ball, in New York. The momentum carried the brand through the 1970s to the 1990s, when Frank Sinatra wore one of their tuxedos.

But by the 2000s, the brand had become more synonymous with cigarettes than smoking jackets. Over the following decade, a slew of creative directors—from Kim Jones to John Ray—tried to revive the brand in vain. Despite their efforts, in 2018, the Business of Fashion reported on parent company Richemont’s “Dunhill Problem,” referencing its more than $110 million in losses in 2017 alone.

Truman Capote, in a Dunhill tuxedo, arrives with Katharine Graham at the Black and White Ball, at New York’s Plaza hotel, in 1966.

Now, though, change may be around the corner. In 2019, Virgil Abloh shocked the fashion world by predicting the death of streetwear in an interview with Dazed: “How many more T-shirts can we own, how many more hoodies, how many sneakers?” Sure enough, in the pandemic’s aftermath, leisurewear feels blander than ever.

Last year, while Holloway was busy taking over the reins at Dunhill, more change was afoot in the fashion world. Magazines from Vogue to GQ discussed the rise of “quiet luxury,” as people veered away from sweatpants clad with garish logos and toward cream-colored cashmere sweaters by Khaite, the Row, and Bottega Veneta instead.

“In the past, we’ve seen Gen Z really lean into statement pieces that were kind of ‘Instagram-worthy,’” Noelle Sciacca, a fashion-industry veteran, told Harper’s Bazaar, “and there’s a shift now into brands that traditionally have been adopted by our older customers.”

“How many more T-shirts can we own, how many more hoodies, how many sneakers?”

This year, the shift is being taken a step further. A new trend called “old money” is proliferating across social-media platforms—think images of Carolyn Bessette-Kennedy, Princess Diana, and Jackie Onassis playing golf and riding horses. The posts tend to feature preppy tennis outfits, tailored suits, large straw hats, and places such as Newport and Cape Cod; the hashtag has accrued more than 230 million posts on TikTok.

The aesthetic is affecting people’s lifestyle choices, too—20-year-olds in Manhattan who’d usually be drinking beers in Dimes Square are heading uptown to Bemelmans Bar at the Carlyle hotel. One Instagram reel sees a group of young women ordering their martinis “shaken, not stirred, please.”

This happens to be exactly the sort of clientele Dunhill aims to attract. “His name is James Bond—that’s the fantasy version. But in reality, you know, it’s men who love to live well,” Holloway says. “Work hard, but they play hard also.”

Left, the gardens of Museo Poldi Pezzoli, where Dunhill presented its collection in Milan; right, Dunhill began as a purveyor of motoring accessories.

In February, Holloway presented his first-ever Dunhill collection at the Duveen Wing in London’s National Portrait Gallery. He veered away from the know-how he’d acquired at Agnona, Narciso Rodriguez, Ralph Lauren, and Jimmy Choo over the decades and dug deep into Dunhill’s rich archives instead. Paintings by members of the Windrush generation provided a symbolic backdrop for his corduroy slacks, leather car coats, and 1930s dinner tuxedos.

A few days later, Women’s Wear Daily headlined its story on the night as “A Debut That’s the Talk of the Town” and reported that the brand was “making tailoring exciting again.”

The expression feels like an oxymoron. Did tailoring ever cease to be exciting? Or has Holloway simply tapped into what the world wants?

“We’ve noticed a huge interest level from an entire generation of men who have grown up with hooded sweatshirts,” Holloway says, “and are just in love with the idea of elegance and tailoring and haberdashery.”

In February, Holloway presented his first collection for Dunhill at the National Portrait Gallery in London.

He is, he tells me, designing for young men who want to wear a morning suit to their friend’s wedding or would love to have monochrome luggage sets to match their car. These men are not looking for androgyny, or for the avant-garde. They want to revel in the simplicity of British tradition.

In a world where fast fashion reigns supreme, the craftsmanship of artisans tailoring natural fabrics might soon prove to be the ultimate status symbol once again.

As Holloway says, “This is about taking it back, and making clothes for the man that fashion has forgotten.”

Elena Clavarino is a Senior Editor at AIR MAIL