For important occasions, both Legge-Bourke and Middleton keep it simple. The former donned a black and white suit and black pumps for the memorial service of Sarah, the Duchess of York's mother, in London—while Middleton graduated from St. Andrews University in a similarly monochromatic ensemble, down to the shoes.
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Prince William and his fiancée have been known to hit the slopes in Klosters, Switzerland—something he used to do with Legge-Bourke. Legge-Bourke was reportedly quite the daring one—the royal staffer allegedly allowed the princes to climb down a 160-foot dam in the mountains toward the end of her professional stint with them.
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Two years after officially joining the royal staff, Legge-Bourke had perfected the preppy look. Her pencil skirt, collared shirt, and belted waist create a timeless ensemble that Middleton made her own wardrobe after at Britain's annual sporting event, Game Fair.
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Though typically conservative when it comes to attire (Middleton's notoriously sexy fashion show aside), both women opted for red to spice up their neutrals on special occasions. Here, Legge-Bourke wears a crushed velvet blazer in crimson with a black camisole in 1997 while Middleton covered up at the Sovereign's Parade at the Royal Military Academy in 2006 in a cherry overcoat.
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With sparkling, almond-shaped blue eyes, wavy locks, and sweet half-smiles, both Legge-Bourke and Middleton boast a classically beautiful, yet relatable look.
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For special occasions, both Legge-Bourke and Middleton have been known to don the classic British accessory—an extravagant hat. Legge-Bourke's donned a powder-blue feathered hat at the Duke of Edinburgh's 60th Diamond Wedding Anniversary service in 2007, while Middleton perfected the feathered look at Laura Parker Bowles' 2006 wedding.
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