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Decades after her tragic death, Princess Diana's status as a fashion icon endures. When she first became a working royal, her outfits were pretty conservative. Even so, they were intended to put her in the spotlight. "The rule was to make her as noticeable as possible. It wasn't to make her shrink, it was to make her stand out," designer Bruce Oldfield recalled to The Times . As time went on, the princess' rebellious streak emerged. Diana broke strict royal rules on several occasions, including protocol about fashion, like skipping gloves during royal appearances. While that might seem like a minor infraction, Diana eventually challenged so many aspects of royal dress that she racked up quite a list of inappropriate outfits

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