Step aside, Kate Middleton – there’s a new “it” royal in town. Almost 75 years after she caused a constitutional crisis in Britain, Bessie Wallis Simpson – the woman who rocked the world with a certain royal romance (Simpson was an American divorcée whose third husband, Prince Edward, Duke of Windsor, formerly King Edward VIII of the England, abdicated his throne to marry her) – has become the latest sartorial obsession for fashion-dom and inspired a host of fall trends.


From the moment she entered the spotlight style watchers breathlessly followed the controversial coupling of Edward, Duke of Windsor and the effortlessly chic American socialite. The media documented the Duchess’ wardrobe choices – Mainbocher, Madame Gres, Christian Dior – and, even decades after the King’s abdication, chronicled the star-crossed lovers comings and goings with paparazzi-like fervor.


Madonna’s new movie W.E. has, undoubtedly, put the focus back on Simpson. Directed by the pop star herself (a woman who knows something about courting controversy), the biopic not only hopes to shed new light on Simpson’s life, but, perhaps inadvertently, also turns the attention once again to one of the biggest jewellery collections of the 20th century.

The Duchess of Windsor’s taste in audacious bijoux was legendary and W.E. costume designer Arianne Phillips pored over the archives to recreate the looks. Cartier provided a number of sparkly replicas (some of which Madonna sported on the red carpet at TIFF to promote the film), but it was the dazzling diamond Zip necklace by Van Cleef & Arpels’ that became a symbol of Simpson’s impeccable taste. A feat of micro-engineering and couture craftsmanship, the haute joaillerie design lay dormant for a half century until just this year, when the storied bauble brand chose to revive the ultra-luxe fastener in four fetching new hues.

Simpson’s extravagances extended to her footwear as well. A devotee of iconic Italian cobbler Salvatore Ferragamo, the well-heeled Duchess regularly teetered on his spindly creations. How timely then that Ferragamo’s creative director, Massimiliano Giornetti, is bringing the look back this season with 28 new versions—among them a black croc style with a metal toe, a wool pinstriped pair, and a glitzy black crystal-encrusted duo worthy of any palace.

More on Simpson’s iconic style – think wasp-waisted gowns and lobster print) – on the next page…



The woman who famously remarked, “you can never be too rich or too thin” wore fashion exceedingly well. She might have had a penchant for elegant, fuss-free clothes (think wasp-waisted gowns or modern shifts to show off her slim figure), but the socialite also liked her fashion with a dose of fun – stealing the spotlight in surrealist lobster-print Sciaparelli gowns and Givenchy dresses playfully embroidered with mini monkeys. Not surprisingly, a coterie of designers drew inspiration from the Duchess for fall, including New York-based Vera Wang and Jonathan Simkhai who both channeled her glamour and innate elegance with rich arisocratic pieces. Most recently, Roland Mouret created an exquisite gold and diamond-embossed silk gown, appropriately named the “Wallis,” as a tribute to Simpson’s iconic style.

In That Woman the hotly anticipated new book about the life of Wallis Simpson, author Anne Sebba reveals the psychology behind Simpson’s fashion sense: "My husband gave up everything for me… I’m not a beautiful woman. I’m nothing to look at, so the only thing I can do is dress better than anyone else. 

If everyone looks at me when I enter a room, my husband can feel proud of me. That’s my chief responsibility.” A true arbiter of style, Simpson may not have been welcome at the British Royal Court but, with her wit and fearless approach to fashion, she’s certainly earned her crown.

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