The Duke of Windsor



It’s hard to isolate legendary figures in the development of fashion – who knows who the first person to roll their jeans was? Who first decided to tuck his pants into his boots? But from this historical ambiguity, there have been a select few whose personal style helped transform what was understood to be classic menswear, and their appreciation of fit and pattern paved the way for what we know today.


Within classic menswear, Prince Edward, the Duke of Windsor, the namesake of the Windsor and half-Windsor knot stands out. Born in 1894 to King George V, Edward was the eldest son and heir to the throne. After his father’s death in 1936, Edward became king, but his playboy lifestyle and his pursuit of a divorced American, Wallis Simpson, caused a constitutional crisis and led to Edward abdicating in favor of his younger brother, Albert. After leaving the throne, Edward, who kept his title as Duke of Windsor, married Simpson and spent time living in the Caribbean and France.


While the Duke’s personal life reads like a sordid novel – part of the trouble surrounding Simpson in the 1930s was that she was rumored to be a lover of Joachim von Ribbentrop, the Nazi ambassador to the United Kingdom – his taste in clothing was impeccable. As a member of the British Royal Family, Edward was clothed in the finest bespoke clothing, produced by tailors and cobblers whose names even today are synonymous with quality. Beyond his wealth, Edward had an eye for color, pattern and silhouette. Although very short – he likely stood around 5’4 – his sharply tailored suits with smooth lines lent him the height he lacked, and in pictures he looks imposing. All of his clothing was impeccably fitted, and displays the sense of casual elegance that we should all aspire to.


During his life Edward used a variety of tailors. The majority of his jackets were made by Scholte, a London tailor that went out of business, while he had his pants made by a series of tailors in the United States. He favored pairing loud odd jackets with muted, wider-leg pants with deep pleats, and many of his hundreds of shoes were bright spectators that lent his more formal suits a casual air. He avoided the braces and high-cut fishtail trousers that were popular during his youth.


The ultimate testament to his fashion sense is the timelessness of some of his outfits. While his bright madras jackets with turn back cuffs may have aged poorly, his classic dark double-breasted suits look straight out of a contemporary magazine. Perfection.


Want to know more? After his death and the death of Wallis Simpson, Sotheby’s auctioned off the Duke’s possessions, including his clothing. As part of this auction, Sotheby’s produced an extensive auction catalog, which features pictures of hundreds of the Duke’s outfits. If you’re lucky, you can snag a set of the books on eBay.

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