Dunhill’s Simon Holloway on Modernizing the Heritage Brit Brand That Dressed Sinatra and Capote

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When Simon Holloway took the reins as creative director of Dunhill last year, he also became keeper to the brand’s rich 130-year legacy. Originally designed to outfit early motorists in the late 19th century, the house is today an icon of British classicism and craftsmanship from refined leather goods to Dunhill’s classic navy blazer that was once the brand’s hallmark item. Over the years, its star-studded list of patrons has included the likes of Frank Sinatra, Truman Capote and the Duke of Windsor. 

Following a four-year hiatus, Dunhill, which is owned by Richemont, returned to the London Fashion Week stage in February with an intimate 41-look Fall/Winter 2024 show set in the Duveen Wing of London’s recently renovated National Portrait Gallery. As Holloway tells The Hollywood Reporter, the intention for his debut show was to showcase his vision for the brand: telling a story of timeless heritage in a modern context. 

“We made it more like a salon as opposed to a big, glossy runway show because it really fit well with this house,” Holloway says during an interview at Los Angeles’ Chateau Marmont. “We wanted people to feel quite immersed and quite close to the clothes. The casting reflected that too. It was very multi-ethnic, with different age groups and older guys that you haven’t seen for a while on the runway — just bring a sense of character into the presentation as well.” The Fall Winter 2024 presentation drew such celebs as Ted Lasso‘s Phil Dunster, model-actor Hu Bing and Shadow and Bone star Archie Renaux.

Beneath paintings of European royals, Dunhill’s models donned lighter, more contemporary takes on pieces that Holloway earmarked from the brand’s catalogs. An archival leather car coat was modernized with French plonge leather and lined in sumptuous camel hair. Stiff tweed jackets were refitted with more breathable cashmere wool blends from Scotland. And there were also Holloway’s personal touches, like V-neck sweaters touting the new Dunhill monogram, paired with herringbone trousers. Dunhill’s Fall/Winter 2024 collection, now hitting retail, is available through dunhill.com, at Dunhill in New York City, and through Neiman Marcus stores (in Los Angeles, San Francisco and Chicago) and Mr. Porter.

Dunhill 1893 Woven Harness Zipped Pouch

$950 at Dunhill

“We have great pieces from the archive that are all in these shades of toffee-color leather. So that was really the starting point of the color palette,” Holloway says, gesturing towards items such as a trench coat and field jacket on mannequins in one of the Chateau’s bungalows. “But we’ve modernized the fit and color, and casualized everything. It’s just this very easy but still dressy kind of feeling. There’s a lot of what I like to call invisible innovation in the clothes, whether it be the lightness of the canvas and the tailoring or the finesse that you get on the leather pieces.” 

Bridging heritage with innovation is core to the Dunhill story, which started in 1893 when eponymous founder Alfred Dunhill inherited his father’s saddlery. It was a watershed moment in technological history, when horse-drawn transportation gave way to prototypical motorcars — and Dunhill responded by shifting from equestrian apparel to pieces meant for motorists. 

“[Alfred] saw the writing on the wall and converted [Dunhill] into the purveyor of everything but the automobile itself,” Holloway explains. “It was tweed coats, innovative leather outerwear, and even the hard instruments that went on the dashboards — clocks, voltmeters and tongue-in-cheek decorative objects.”

Dunhill Bulldog Onyx Black Cufflinks

$550 at Dunhill

Indeed, it wasn’t just the utility of Dunhill’s accessories that defined the house, but also the founder’s personal quirkiness and a quintessentially British cheekiness, exemplified by a signature hood ornament featuring the brand mascot, a dog called Tweenie. As the house legend maintains, the devilish canine, who is seen thumbing his nose mockingly, was born of Alfred’s personal distaste for the police. 

“Alfred Dunhill was one of the first people in England to be given a fine for speeding — he had a visceral hatred for the police,” Holloway notes. “This is the kind of heritage we have the pleasure to play with. We have the serious side in that he was obsessed with luxury, having made things to an incredibly high level of spec. But then there was also this flip side to him, which was archly eccentric and quite British.” 

Despite the humor woven into the brand DNA, Holloway says he also wants to maintain an acute air of luxury about its clothing. While traversing the archives, he says he was also struck by a sense of old Hollywood glamour. He references a double-breasted cashmere blazer with a pair of silver flannel driving gloves from the latest collection as “Bond-esque.” And as he moves into another part of the Chateau Marmont bungalow, he opens up an armoire to reveal two pieces that reside in the Dunhill archives that the house has flown into Los Angeles for a reveal: a dinner suit made for Frank Sinatra and a tuxedo jacket made for Truman Capote that the diminutive author wore for his famous 1960s Black and White Ball.

“Dunhill has a reputation for being a destination of English glamour — maybe it was the smoking accessories, which are among our most enduring icons,” says Holloway. “I really love the idea that movie stars looked like movie stars. A lot of the references we had in our mood boards were pictures of Carrie Grant, David Niven, and the Duke of Windsor, who was a longtime client at Dunhill and had possibly one of the best quintessentially English wardrobes ever curated.” 

According to Holloway, nurturing Dunhill’s relationships with artisanal suppliers is crucial to his view of luxury. The house currently works with about 15 suppliers, ranging from feather and button makers to shoemakers and hatmakers. Embroidering meanwhile is done by the regimental embroidery in London, which chiefly produces military uniforms.

“A lot of the relationships with the fabric mills are really important to me because, for a collection like this that embraces timelessness and classism, the origin of everything is fabric,” Holloway says. “We are textile designers before we even get to cutting a piece of cloth. So it’s all done with certain provenance as well and kind of all about that level of geekiness when it comes to the craftsmanship.”

While paying homage to tradition, Holloway says he’s keenly aware that Dunhill’s future requires new audiences. On one front, that means reaching younger consumers who he says are increasingly interested in traditional tailoring, citing a resurgence of old-guard haberdasheries in London. And on another, it means maintaining a presence in key international markets: Holloway says Dunhill’s London-based bespoke service regularly sends its tailors to the United States, China and Japan. 

“The thing about Dunhill was that it was really created as an English house for an international audience,” Holloway says, noting that Dunhill had opened in New York and Paris as early as the 1920s. “It was very international from quite an early period of time. And I think that that’s something I’d like to keep very much in my forethoughts as we continue the redevelopment of Dunhill.”

As for the iconic Dunhill motoring products of yesteryear, they’re still available in rarefied situations, which in a sense, echoes the early days of the brand when driving was still a relative luxury and niche pursuit. In recent years, Holloway says he’s seen an increase in appetite across fashion and accessories for limited-edition collectibles — at Dunhill, that means everything from table lighters to car upholstering. These requests present a different, more whimsical opportunity to dive into the brand’s older catalogs. 

“That’s just the way the whole luxury industry is moving — people want things that are the most exclusive, that nobody else can have,” he says. “The amazing thing about Dunhill is that we’re still able to make some of these things that nobody else can make. Going forward, who knows? There might be all sorts of things we end up doing tailored to various clients.”