Princess Margaret
Just like her older sister, Queen Elizabeth, was the perfect princess, Princess Margaret was the typical rebellious younger sister. After one very public love affair with an older man, Margaret continued to live a renegade life, which included heavy drinking, heavy smoking, an infamous party life and (allegedly) an affair with Mick Jagger.
Princess Sofia of Sweden
Prince Carl Philip of Sweden raised eyebrows when, a year after breaking up with his partner of 10 years, he began dating Sofia Hellqvist, a model. During her career as a model, Hellqvist worked as a glamour model, appeared in the pages of Swedish men's magazine Slitz and (allegedly!) made out with adult film star Jenna Jameson on the set of reality show Paradise Hotel.
Princess Stéphanie of Monaco
Next to her brief careers in fashion (as an apprentice at Christian Dior) and music (she has released two album to 'disappointing' reviews), Princess Stéphanie courted international attention when she had a baby girl named Camille out of wedlock and refused to tell anyone who her father was. Shortly after, the Princess began a relationship with 'married elephant trainer Franco Knie,' during which she moved into his 'circus caravan' with her three children. After that, she married acrobat Adans Lopez Peres, a member of her ex-boyfriend's circus. They were married for 10 months.
Meghan, Duchess of Sussex
Since meeting and marrying Prince Harry in 2017, Meghan Markle—now the Duchess of Sussex—has been accused multiple times of 'royal rule-breaking'… albeit unintentionally. From her ripped jeans to her messy buns, her friendship circle and even—gasp—jetting off to New York for a private baby shower, Meghan is generally considered to be a royal rebel.
Wallis, Duchess of Windsor and Prince Edward, Duke of Windsor
There's "rebellious" then there's "giving up your throne to marry your girlfriend" rebellious. Wallis Simpson and the then-King Edward VIII were the centre of tabloid attention for years when the king attempted to marry his American divorcee lover. When he was not allowed to marry her (and therefore make her queen), he abdicated his throne, married her and took the lesser title, 'Duke of Windsor.'
But forsaken thrones weren't the only controversy surrounding Wallis and Edward (known to friends and family as 'David'). They were also thought to be Nazi sympathisers and lived a infamously 'freewheeling' life in France together, where they threw parties and became embroiled in New York's 'café society'.
Diana, Princess of Wales
Both before and after her ill-fated marriage to Prince Charles, Lady Diana Spencer—later the Princess of Wales—never paid attention to the rules. Whether it was walking in landmine sites, hugging HIV positive patients, dating billionaires or being photographed in swimsuits, Diana always made headlines.
Princes Harry
Known as the royal family's 'bad boy' (until he settled down with his American princess, that is), Prince Harry has been involved in his fair share of controversies. From wearing a Nazi uniform to a costume party to having his naked photos leaked, Harry is no stranger to tabloid headlines.
Sarah, Duchess of York
Ever since Prince Andrew announced his engagement to bubbly redhead Sarah Ferguson—quite the contrast to primp and proper Lady Diana—the Duchess of York has courted controversy. When the couple divorced in 1996, Princess Margaret reportedly wrote a letter to her claiming she had "done more to bring shame on the family than could ever have been imagined".
Caroline, Princess of Hanover
Although nowadays she's a regal mother and grandmother with a very covetable Chanel wardrobe, Princess Caroline of Monaco—now Caroline, Princess of Hanover—had quite the colourful past. Prior to her marriage to French venture capitalist Philippe Junot, Caroline was linked to various well-known men including "Mark Shand, the younger brother of Camilla, Duchess of Cornwall; Guillermo Vilas; Sebastian Taylor, who had previously dated Princess Elizabeth of Yugoslavia; Jonathan Guinness, the son of Jonathan Guinness, 3rd Baron Moyne; Henri Giscard d'Estaing, the son of former President of France Valéry Giscard d'Estaing; and French singer Philippe Lavil."
