Inspiring men: timeless style icons of the 20th century

Throughout history, certain individuals have transcended their fields to become cultural icons remembered as much for their contributions as for their indelible personal style. From politicians who shaped nations to actors who illuminated the silver screen, the 20th century produced many men whose daring fashion choices still inspire today. Meet the stylish visionaries whose uniqueness of dress left an enduring mark on the trends and attitudes of their era.

Across decades, certain individuals have attained a level of sartorial mastery that transcends trends and remains relevant for generations. Through meticulous tailoring, thoughtful ensemble choices, or a confident personal flair, some men have defined what it means to wear clothing effortlessly and with panache. As we transition styles for a new season, we would be wise to examine the timeless elegance set by our finest 20th-century icons. These visionaries possessed an innate sense of personal expression through their fashion that still inspires today. Revisit their influential looks for a fresh take on versatile, lifelong style.

Sydney Poitier

While Bahamian-American actor, director and activist Sydney Poitier did not place great emphasis on extremes in fashion, it was his nonchalant yet refined style that has cemented his influence. Big knit jumpers, supple sheepskin-lined coats, neatly fitted polo shirts and relaxed denim composed his everyday uniform - clothes that required little maintenance but exuded sophistication. Poitier had a gift for mixing separates in a way that appeared completely natural and at ease. Though he made style seem like an afterthought, it was this effortlessly chic sensibility that has inspired mood boards at top fashion brands. Poitier's signature look proved that understated elegance and comfort need not be mutually exclusive, a lesson his appearances continue to impart to this day.

Yves Saint Laurent

As the illustrious creative force behind the houses of Dior and his own global powerhouse brand, Yves Saint Laurent was no stranger to transforming fashion. But beyond his revolutionary runway contributions, the legendary designer epitomized effortless Parisian chic through his own idiosyncratic sense of personal style. Sharp tailoring, bootcut denim, worn-in shirts, and signature thick-rimmed eyewear comprised Saint Laurent's wardrobe - looks he imbued with rebellious rockstar energy. His embrace of nascent counterculture movements trickled down into the styles of millions. Saint Laurent, perhaps more than any other, understood the symbiotic relationship between high fashion and streetwear decades before it became commonplace. That his aesthetic choices still permeate modern wardrobes is a testament to both his impeccable taste and far-reaching influence on how men and women express themselves through clothing. An original tastemaker in every sense, Saint Laurent left an indelible mark on global style.

Gregory Peck

Gregory Peck's effortless charisma and chiselled good looks made him a star of Hollywood's Golden Era. But beyond screen presence, Peck demonstrated impeccable sartorial flair, mastering traditionally tricky pieces with stylish nonchalance. Off-white three-piece suits, tailored to emphasize his athletic build, became a Peck signature that defined the sophisticated 1950s leading man. A proponent of cultivating long-term relationships with esteemed custom clothiers, Peck treated fashion as an art form to perfect - transforming screen alter-egos into models of aesthetic aspiration. While many actors simply wear costumes, Peck internalized the power of presentation, making timeless style as much a part of his on-camera magnetism as skilful line delivery. Even amongst legendary mid-century matinee idols, Peck stands apart for the way he seamlessly blended acting talent with a refined personal panache that still dazzles viewers today.

Steve McQueen

As one of cinema's first true style icons, few have been as instrumental in popularizing now-classic looks as Steve McQueen. Whether rugged denim jeans, warm cable-knit sweaters or buttery-soft leather jackets, McQueen incarnated menswear staples with a rebellious flair that defined 1960s cool. Offscreen as much as on, he blended rugged masculinity with Old Hollywood glamour in a way that seems effortless, though its impact was seismic. So potent is McQueen's influence that even decades later, his subtle uniform of refined Americana remains supremely appealing. With relaxed good looks and bad boy charm to match, McQueen forged the template for many an actor and celebrity to follow. His indelible brand of casually cool sophistication ensures "The King of Cool" moniker is well-earned and his singular style continually draws fresh admirers. McQueen's impact lives on as both a source of inspiration and a reminder that sometimes less really is more.

Jack Kerouac

As a progenitor of the influential Beat Generation literary movement, Jack Kerouac incarnated its casual nonconformity through his relaxed personal style. Embracing functional labour like sturdy trousers, worn boots and weather-beaten denim as not just attire but an aesthetic protest, Kerouac epitomized the casual rebel intellectual. Rejecting flashy excess, he chose understated essentials that conveyed cool through lived-in integrity alone. From meandering journeys chronicled in iconic works like On the Road to simply sitting pen to page, Kerouac imbued everyday effort with poetry that shaped counterculture. That his working class-inspired uniform of simple joy, discomfort and independence became so widely copied is a testament to its authenticity and mass appeal. With legendary status as a true artist who walked the road less traveled, Kerouac stands as both muse and prototype for creative nonconformists to follow—making this seminal Beat's legacy as fresh and inspiring as the summer breezes he celebrated within unforgettable prose.