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10 Princesses Who Broke The Rules & 10 Who Played By The Book


10 Princesses Who Broke The Rules & 10 Who Played By The Book


Life Isn't A Fairy Tale

Princesses aren't always sweet and demure; in fact some are rebellious, nasty, and downright fraudulent! Some princesses did as they were told, while others struggled with the roles they were granted. All these women were complex characters, nothing like the fairytale princesses you grew up with.

File:Princess of Wales in 2023 (cropped)02.JPGIan Jones on Wikimedia

1. Stephanie Von Hohenlohe

Let's start things off with a bang: Stephanie von Hohenlohe was an illegitimate child from a common background who married an Austro-Hungarian prince while pregnant with an illegitimate child of her own. She was also, despite being Jewish, a Nazi spy. After divorcing her princely husband, Stephanie snuggled up to fascist sympathizers as well as members of Hitler's inner circle.

File:La princesse Stéphanie de Hohenlohe - btv1b530737489.jpgAgence Rol. Agence photographique (commanditaire) on Wikimedia

2. Princess Pingyang

Sometimes, you have to break the rules to right a wrong, something which Princess Pingyang knew well. The daughter of a general, Pingyang become the first female general of the Tang dynasty with more than 70,000 soldiers in her ranks. Her army contributed to the downfall of a corrupt emperor, and helped usher in the Chinese golden age.

File:唐公主(說唐演義全傳).jpgUnknown authorUnknown author on Wikimedia

3. Olga Of Kyiv

In comparison to Pingyang, Olga of Kyiv was a princess with a bodycount in the thousands. After her unpopular husband met an unfortunate demise, Olga took revenge into her own hands, by releasing an army of sulfurous pigeons upon her enemy's village, burning it to the ground. She was later canonized as a saint.

File:Княгиня Ольга (в крещении Елена). Чтец-3.pngUnknown authorUnknown author on Wikimedia

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4. Wu Zetian

Wu Zetian first stepped foot in the palace as an imperial concubine, and ended life as Emperor of China. Wu used her beauty and intelligence to gradually climb the rungs of the imperial ladder, until she was the emperor's chief wife. Disposing of rivals and pesky children as she rose, Wu acted as both emperor and empress, dowager to her son, and ruler in her own right.

File:Wuhou (2).jpgUnknown authorUnknown author on Wikimedia

5. Christina Of Sweden

Educated like a boy, with plenty of exercise, book learning, and swashbuckling, Christina of Sweden was fond of fencing, Catholicism, and other princesses. It was the Catholicism rather than her sexuality which caused problems for Lutheran Sweden. Christina's refusal to marry led to her abdicating the throne in favor of her cousin, and converting to Catholicism.

File:David Beck - Christina, Queen of Sweden 1644-1654 - Google Art Project.jpgDavid Beck on Wikimedia

6. Pauline Bonaparte

With how buttoned-up modern princesses are, it's almost unthinkable that one would pose in the nude, but that's exactly what Pauline Bonaparte did. Napoleon's younger sister had a reputation for promiscuity, throwing bacchanalian parties, and posing sans clothing for sculpture Antonio Canova. When Canova suggested Pauline pose as Diana the huntress instead, she responded that nobody would believe her chastity.'

File:Pauline Bonaparte princesse Borghese.jpgMarie-Guillemine Benoist on Wikimedia

7. Princess Margaret

In contrast to the responsibilities Elizabeth II shouldered as queen, her younger sister, Margaret, was living it up during the Swinging Sixties. The party princess was a rebel from childhood, when she was known to bite her sister during quarrels. Eventually, this behavior made it into a public eye; a heavy drinker and smoker, Margaret was photographed in nightclubs with the Beatles and Louis Armstrong.

File:Princess Margaret 1950 (F1257 s1057 it4930).jpgAlexandra Studio on Wikimedia

8. Princess Caraboo

Wearing exotic clothing and speaking a language nobody could understand, Princess Caraboo was the first exposure England had to the tropical island of Javasu. There has only one hitch: Javasu was as phony as Caraboo's story of her mother being eaten by cannibals. Caraboo was actually a cobbler's daughter named Mary Willcocks, who created this ruse seemingly for love of the game. 

File:Illustration facing page 44, Devonshire Characters and Strange Events.pngNathan Cooper Branwhite, engraver on Wikimedia

9. Diana Spencer

Hear us out before you start typing angry comments about besmirching Diana's name: sometimes, a little rebellion is exactly what the crown needs. Diana marched to the beat of her own drum, whether it was by competing in field races with other mothers or holding hands with HIV patients despite the stigma. Diana's divorce and subsequent openness about the royal family's influence on her mental health opened the floodgates for further activism and transparency around these issues.

File:Princess Diana - Royal Visit to Halifax, Nova Scotia - June 1983 (37448879456).jpgRuss2009 on Wikimedia

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10. Pauline Von Metternich

Pauline von Metternich was one of the most fashionable and educated women of the 19th century, and one of the last great royal patrons of the arts. So, what exactly did she do to end up on this list? Well, in 1892, Pauline's opinions over floral arrangements led to her dueling with a countess, which they did scandalously stripped down to their corsets to avoid infection or dirtying their clothes.

File:Portrait of Pauline Princess von Metternich-Sandor.jpgArtist of 19th century on Wikimedia

Now that we've discussed a few princesses who forged new paths, let's look at a few who stuck to the rules.

1. Menen Asfaw

As Empress of Ethiopia, Menen Asfaw was everything a noblewoman ought to be: pious, dutiful, and a right hand to her husband. Like Diana, Menen was known for her charity work, acting as patroness to the red cross, and founding a school for girls across Ethiopia. Following the Italian occupation of Ethiopia, Menen donated her crown to the Church of the Nativity in Bethlehem.

File:Menen Asfaw (impératrice d'Ethiopie) (CN) - btv1b53228939t.jpgCentral News (Agence photographique). Agence photographique pour le document reproduit (commanditaire) Agence Rol. Agence photographique (commanditaire) on Wikimedia

2. Soraya Tarzi

Truthfully, Soraya Tarzi could have belonged on either side of this list. Both Queen Consort of Minister of Education of Afghanistan, Soraya crusade for the unveiling of women, rallied against polygamy, and founded Afghanistan's first magazine for women. And yet, she did this all through official diplomatic channels, with the approval of her husband, who also believed in women's rights.

File:Queen Soraya of Afghanistan.jpgUnknown authorUnknown author on Wikimedia

3. Kate Middleton

To a large section of the British public, Princess Catherine can do no wrong. Called "the monarchy's greatest asset", Kate has helped bring the British Royal Family into modernity, encouraging further charity work focusing on children and mental health. Perhaps Kate's strength is the public eye is her desire to stay out of it, her privacy keeping her out of scandal.

File:Trooping the Colour (Hurley) 2025-06-14-11-17-A.jpgLauren Hurley / No 10 Downing Street on Wikimedia

4. Marie Of Romania

As a princess, Marie of Romania was popular, as a queen, there was nobody more loved. During WWI, Marie devoted her time to treating the wounded, aiding the red cross, visiting hospital, and transporting wounded soldiers to the hospital. In addition to her talents in painting, dancing, and horseback-riding, Marie was also an accomplished author, publishing 34 books. 

File:Queen Mary of Romania 2.jpgUnknown photographer on Wikimedia

5. Seondeok

Wise and kind, Seondeok was the first queen of Silla (now Korea), and she didn't have to take out any opponents to get there. Though Seondeok's reign was initially met with skepticism—some officials planned an uprising—she quickly won over both her public and her advisors. Seondeok's reign brought upon a Sillan renaissance in literature, art, and, especially, astronomy.

File:경주 남산 불곡 마애여래좌상 01.jpgDalgial on Wikimedia

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6. Empress Elisabeth

Empress Elisabeth—or, Sisi, as she was known—was everything a princess ought to be: beautiful, charitable and intelligent. However, Sisi's popularity could not compensate for her turbulent personal life; she struggled with her mental health all her life, particularly her relationship to food, body image, and athleticism. Even though she seemingly did everything right, she still met a grisly end.

File:Elisabeth of Austria, by Franz Xaver Winterhalter.jpgFranz Xaver Winterhalter on Wikimedia

7. Olga Nikolaevna

The oldest Romanov daughter, Grand Duchess Olga often took responsibility for her younger siblings. From childhood, Olga was known for her compassion towards others, donating portions of her inheritance to chaity, and treating wounded soldiers alongside her mother and younger sister. While Olga was not a perfect saint (she could be moody and struggled with her temper) she never let personal issues usurp the greater good.

File:Olgachair.jpgPhoto studio Boasson and Eggler, Saint Petersburg, Nevsky 24.; State Archive of the Russian Federation on Wikimedia

8. Grace Kelly

Though Grace Kelly was not born into royalty, her prim and proper demeanor made her a stark contrast to the other Hollywood stars of the era. After marrying Rainier III of Monaco, Grace gave up her acting career and dedicated her life to her new subjects. In addition to working with the red cross and several other Monégasque charities, she also founded an international charity in partnership with UNICEF, to benefit children around the world.

File:Grace Kelly Promotional Photograph Rear Window.jpgParamount publicity photographer. on Wikimedia

9. Empress Masako

Another commoner who married into royalty, Empress Masako embodies the resilience of modern Japan. Despite personal struggles and a succession crisis, Masako has weathered her transition from diplomat to princess to empress with grace. Masako's openness about her struggles with mental health & fertility have made her a role model for Japanese women.

File:Empress Masako at TICAD7.jpgTICAD7 Photographs on Wikimedia

10. Kaʻiulani

The last princess of the Kingdom of Hawaiʻi, Kaʻiulani was born into a turbulent dynasty. Like other princesses, Kaʻiulani was given a premium education in England, and her poise and tact challenged western notions of what native Hawaiians could be. Despite this, she could not prevent her country being annexed to the United States for the sake of corporate greed.

File:Kaiulani in 1897, wearing pearl necklace (PPWD-15-3.016, restored).jpgUnknown authorUnknown author on Wikimedia


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