Simon Holloway, appointed creative director of the British luxury house Dunhill in April 2023, brings to the brand a deep reservoir of experience drawn from his previous roles at prestigious fashion houses such as James Purdey & Sons, Agnona, Ralph Lauren, and Narciso Rodriguez. His arrival marked a fresh chapter for Dunhill, which has its origins in 1893 when Alfred Dunhill took over his father’s saddlery business and transformed it into a symbol of British refinement and automotive culture.
Now under the ownership of the Richemont luxury group, Dunhill has evolved significantly from its beginnings as a maker of motoring accessories into a full-scale luxury menswear label. Holloway personifies the dual nature of the brand, comfortably straddling the worlds of aristocracy and rock culture while embracing a sense of quiet, understated elegance. His creative direction emphasizes classical values with a lighter, more joyful, and relaxed sensibility—deliberately steering away from the stiffness commonly associated with traditional British tailoring. As Holloway notes, he prefers to make people’s lives easier through design rather than complicate them.
Reflecting on his appointment, Holloway describes the role as a personal and emotional connection to his roots. He recalls how his father, a well-traveled businessman, embodied a quintessential British elegance with his blue blazers—making Dunhill a brand that always represented the pinnacle of menswear in his eyes. This deep-seated appreciation for the brand’s legacy inspired Holloway to build on its historic intuition, especially its early focus on the automobile and its influence on men’s accessories and fashion in the twentieth century.
Speaking on Dunhill’s current direction, Holloway emphasized how the post-war years saw the brand gain renown for its tailored suits, offering a more fluid alternative to the rigid expectations of Savile Row. Iconic black-tie attire, like the suits worn by Frank Sinatra and Truman Capote at the legendary Black and White Ball in 1966, remains central to the brand’s visual identity. Today, Dunhill integrates traditional British wardrobe codes with modern lightweight tailoring, the result of nearly four decades of Italian craftsmanship. Holloway explained how their jackets strike a balance between a structured silhouette and a softer, more relaxed feel. The garments retain an English sensibility but avoid the exaggerated lengths of overseas styles, blending sportiness with elegance in a uniquely modern approach.
This renewed style has the potential to appeal even to younger audiences unfamiliar with formalwear. Holloway acknowledged a generational shift: many young people have never seen their parents or grandparents in suits, making them more curious and open to experimenting with tailored pieces. Rather than adhering to dress codes, suits become a form of personal expression, even a statement of counterculture. In London, he observes young individuals buying vintage suits, mixing velvet jackets with jeans, and setting their own rules—an approach Holloway finds incredibly refreshing.
The traditional association of suits with boardrooms is also being reimagined. Holloway shared an anecdote about a musician friend—bassist for one of the UK’s biggest bands—who asked him to design a couple of suits. After wearing one on stage, the artist told Holloway the suit enhanced not just his posture but his performance. For Holloway, this interaction highlights how elegance today is about more than appearance; it’s about how clothing influences confidence and expression, even for those in unconventional professions.
Designing menswear in this evolving landscape brings its own set of challenges, but Holloway sees it as an opportunity to inject joy into the category. Many men, he says, genuinely enjoy shopping and seek entire wardrobes rather than single pieces. His goal is to provide them with beautifully crafted clothing made from luxurious fabrics, with excellent workmanship and fair pricing. Unlike many of Dunhill’s competitors in the timeless menswear market, the brand aims to remain accessible without sacrificing quality.
When asked how men should dress today, Holloway advocates for a rediscovery of timeless beauty. He appreciates the allure of classic movie stars who dress with purpose and flair. Though modern red carpets are often populated by celebrities forgoing ties and bowties, he believes there’s enduring charm in a fully realized look. Being well-dressed, or even slightly overdressed, still carries power and appeal in an increasingly casual world.
Holloway also reflected on the global fascination with British style, attributing much of its appeal to the romantic imagery associated with the royal family and aristocracy. This connection, combined with Britain’s storied history of merging rock culture with royalty—from Princess Margaret’s friendships with the Rolling Stones to Princess Diana’s bond with Elton John and today’s royals like King Charles and his sons—has created a unique and seductive form of English soft power. This blend of tradition and rebellion, formality and informality, defines the spirit of Dunhill and the vision Holloway brings to the brand’s future.
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