Power Dressing: The Gatsby Shirt

The History of Contrast White Collars and Cuffs

The contrast collar shirt, often called the Winchester shirt, has roots in the practical fashions of the Victorian era. During this time, men's dress shirts frequently came with detachable collars and cuffs, allowing for easier cleaning and replacement since collars soiled quickly from daily wear. This design was born out of necessity: starched white collars provided a polished look while the body of the shirt could be coloured or patterned, extending the garment's lifespan. The style gained prominence in the 19th century, named after Oliver Fisher Winchester, the 52nd Lieutenant Governor of Connecticut, though its popularity extended far beyond American politics.

By the early 20th century, contrast collars evolved into a symbol of refinement. In the 1920s, they appeared in various forms, including the long-pointed Spearpoint collar, reflecting the era's shift toward more streamlined menswear. The design waned mid-century but saw a resurgence in the 1960s through retailers like J. Press, where shirts often featured light blue end-on-end or madras bodies paired with white collars and cuffs. This Ivy League influence cemented the contrast collar as a preppy staple, blending aristocracy with everyday elegance. By the 1980s, it had transformed into a power symbol on Wall Street, embodying confidence and professional prowess.

Cinematic Fame

The contrast collar's cultural footprint is as striking as its design. Perhaps its most iconic moment came in the 1987 film Wall Street, where Michael Douglas's character, Gordon Gekko, donned striped shirts with bold white collars and cuffs. These shirts, often paired with suspenders and power suits, symbolised the era's capitalist excess and unbridled ambition - "greed is good," as Gekko famously declared. In HBO's Boardwalk Empire, Nucky Thompson (played by Steve Buscemi) would often sport contrast collars, evoking 1920s Prohibition-era elegance. Even in literature and film inspired by the Jazz Age, such as The Great Gatsby adaptations, the contrast detail hints at old-money opulence. These appearances underscore the shirt's enduring role as a visual shorthand for power, eccentricity, and timeless style.

How to Style It Today

The contrast collar shirt offers a sophisticated twist on classic menswear, balancing formality with versatility. For a modern take, pair it with a well-tailored suit - think charcoal grey or navy - for business or evening events, enhancing the crisp contrast. Opt for conservative patterns like subtle stripes, checks, or solids in pastel shades to keep the look refined and avoid overwhelming the outfit. Tie selection is key: steer clear of bold "power ties" in clashing colours; instead, choose subtle solids or patterns in complementary hues to let the collar shine. Our new season colours offer a fresh yet heritage-inspired option for the discerning gentleman.