The Most Inappropriate Outfits Worn By Princess Charlene

If there's anyone who has struggled to settle into royal life, it has to be Charlene, Princess of Monaco. Formerly Charlene Wittstock — a champion swimmer and Olympian who represented South Africa in the 2000 Summer Games — the athlete's world was turned upside down when she met Albert, Prince of Monaco. The prince first saw his future bride when she was competing in a swimming event in Monaco. In classic blue blood fashion, the prince's aides reached out to the athlete's management team, and the rest is history. 

The two were married in 2011, but the carriage didn't immediately ride them off into the sunset. Tabloids have long speculated that Princess Charlene was pushed into the marriage and lives an unhappy life behind Monaco's palace doors. While this may all just be speculation, the princess herself has opened up to Vogue about her troubles settling into the royal spotlight. One of her trickier trials? Finding her style. 

It seems the aspect of being Monaco's matriarch that the mother of two has struggled with the most has been the public's expectations of fashion excellence. And who could blame her? Before meeting Prince Albert, the athlete's closet was filled with swimming caps and sporty gear. While falling in love can change a person in many ways, filling their closet with royal-approved couture usually isn't one of them. While the Princess of Monaco has since found her footing, let's take a look back at some of Charlene's past fashion faux pas and inappropriate moments.

While Princess Charlene looks stunning in this beaded green gown, she has named this number as enemy No. 1 when it comes to her early fashion crimes. Speaking with Vogue in 2011, just a few months before her royal wedding, the future princess was open about how dressing for her first Red Cross Gala was a stressful, and ultimately unsuccessful, experience. 

"I was literally a fish out of water," she told the publication. "I thought it was all fun, fun, fun, and didn't give my outfit any thought. I had been playing beach volleyball all day, painted my nails red, and threw on a green dress. I thought I looked great at the time, but looking back, I realize that my debut into Monaco society should have been better executed!"

Considering the fact that Monaco's Red Cross Gala is one of the largest charity galas in the world, it's no surprise that the dignitaries and nobles that surrounded Charlene that night would have expected a bit more effort from their future leader. At £2,999 a head, the guest list is usually the who's who of European society. Having been founded in 1948 by Prince Louis II, it has also become quite the treasured tradition in the small principality. With this said, Charlene's strappy, emerald gown definitely flattered the former Olympian's physique, but the skin-bearing dress was perhaps better suited to a glam Hollywood premiere than a time-honored charity event. 

What's in a curtsy? Traditionally, a curtsy is reserved for women and girls when they are greeting someone of higher social rank than themselves. All you have to do is bend your knees quickly, with one foot crossed in front of the other, and voila, you have now respectfully greeted whichever duke, duchess, or princess you are greeting. However, while the actual action is quite simple, remembering the full title and rank of everyone on your guest list — and therefore, who it is appropriate to curtsy to — can be quite the headache. 

Just take it from Princess Charlene of Monaco. In the biography "Charlene: In Search of a Princess," South African writer Arlene Prinsloo translated an interview the royal gave to Rapport, an Afrikaans-language tabloid, in 2019. According to Prinsloo, the Princess of Monaco expressed frustration at herself, saying, "I address royals incorrectly, or often curtsy to those I shouldn't be curtsying to, or I forget to curtsy."

Even worse, Princess Charlene's outfits are often inappropriate for curtsying. Choosing high-end gowns from only the best designers and with only the most flattering silhouettes sounds hard enough, but imagine having to do squats in them — in front of the world. In the same interview with Rapport, Charlene opened up about wardrobe malfunctions she has experienced while curtsying. "The seam of my dress has split," she shared, "and I've also lost an earring in my blouse while curtsying."

From modernizing your wedding vows to switching into some funky shoes for the dance floor to even chopping off your hair before the reception, brides have been implementing more non-traditional wedding ideas in recent years. While you might imagine that these are usually met with happy tears and smiles from the bride's loved ones, a royal wedding is a completely different ballgame. 

Charlene, Princess of Monaco, sure made a splash when she donned her non-traditional suit jacket and palazzo jumpsuit for her civil ceremony to Prince Albert II on July 1, 2011. While the blonde beauty did eventually change into a stunning Armani Privé gown for the couple's Roman-Catholic ceremony the next day, the blazer and pants combo certainly turned heads when the newlyweds waved to their well-wishers from the palace balcony. What's more, the jumpsuit and blazer were different shades of pale blue, not white, which only made the ensemble all the more unconventional. 

As Prinsloo wrote, "The loose culotte pants were a daring gamble for a prospective Grimaldi bride, who in the past all wore dresses or skirt suits to the civil ceremony." Having previously had the privilege of having former movie star Grace Kelly as their princess, one can imagine that the people of Monaco were not prepared for such an edgy look. But hey, Charlene's no stranger to breaking royal protocol.

If you're a prospective princess and you think the media storm might die down after your blockbuster royal wedding, think again. Just ask Meghan Markle, who left the royal family altogether following incessant tabloid harassment, among other issues. While Princess Charlene wasn't tormented quite as badly as Prince Harry's bride, there was a large amount of pressure put on her shoulders following her 2011 wedding to Monaco's Prince Albert II. 

For starters, there was the expectation that the principality's new princess would make a name for herself in the fashion world. However, the gown Princess Charlene wore to Princess Madeleine of Sweden's wedding in 2013 left many royal watchers wanting. As Maddalena Mastrostefano, an expert in European monarchy, told Express, the brown dress and lack of jewels was a "bad PR move" and was not considered appropriate by the people of Monaco. "It was supposed to be tiaras and orders, she arrived with a brown dress and that was it," she said. 

With Prince Albert a no-show, this was Princess Charlene's first solo engagement since her marriage, and it was felt by the chic folk of Monaco that their the lone representative should have made a bigger fashion statement than this ruffled number. While the sheer bolero jacket and peplum shirt piece were interesting pieces, the fit wasn't as perfect as one would hope. What's more, the dark brown color of the gown made her fade into the background of the crowds. 

When Princess Charlene married Prince Albert II, she wasn't just marrying a man — she was also marrying a legacy. For better or worse, a crucial part of that legacy is the timeless style and elegance of Prince Albert's mother, Her Serene Highness, Princess Grace of Monaco. While the Monegasque royal family operated under the radar for many decades, they were thrust into the international spotlight when the American screen star retired from movies to marry Monaco's Prince Rainier III. 

Long before she even met Prince Rainier, Grace Kelly — as she is most widely known — had already carved out a reputation as being one of director Alfred Hitchcock's uber-polished, icy blondes. With her classically feminine silhouettes and austere fashion taste, Grace Kelly was the epitome of "style icon." While Princess Charlene resembles her late mother-in-law in her blondeness and beauty, it seems the new Monegasque matriarch is lacking in the fashion department. 

The gap between Kelly and Princess Charlene was on full display in 2010 when Prince Albert and his then-fiancée attended a private viewing of an exhibition at London's Victoria & Albert Museum titled "Grace Kelly: Style Icon," cataloging Kelly's place as a paragon of 1950s beauty. However, disappointingly, Princess Charlene opted to wear a basic knee-length black dress for this occasion. While this would be a cute number for a cozy date night, it did not meet the mark for an event celebrating Monaco's legendarily chic royal.

Red Cross Gala? More like lilac skirt gala. Princess Charlene swung wide when she opted for this structural ombre gown that bled from pale pink to a shocking iris color. Gone were the days of Prince Albert's then-girlfriend choosing her gala gowns on a whim, as she has admitted to doing at the 2006 gala. However, as beautiful as this floor-sweeping frock may be, there was one element of the dress that put it just over the line of inappropriate.

See that keyhole neckline? While this gap on the bodice surely kept Charlene cool in the Monegasque heat, it also ensured that all eyes were on her chest. If we were to see this feature on our red carpet favorites, like Rihanna or Margot Robbie, it might be met with rounds of applause and fire emojis galore on social media. However, the crowd in attendance of Monaco's largest charity gala was decidedly a different audience. 

Far from the stans, fans, and fashion lovers who might tune into red carpet ceremonies, the guest list of the 2008 Red Cross Gala included the likes of Ivana Trump, former wife of Donald Trump, former State Minister of Monaco Jean Paul Proust, and jeweler Alberto Repossi. Considering the overall conservative nature of the gala, this cleavage-baring gown was just a little too sexy for the event. 

Becoming a royal means that your planner is almost always filled with events like ribbon cuttings, state banquets, and garden parties. That is, unless you're Charlene, Princess of Monaco. The rebel royal made headlines when she appeared at a fashion show for Milan Fashion Week in 2017. For someone whose job it is to be a public servant, rocking out at such an avant-garde event was an unexpected move. However, if there's one thing Princess Charlene has proved good at, it's keeping the tabloids on their toes. 

With her blonde hair sheared into a short bob, Princess Charlene's spiky look announced to the crowd and the cameras alike that she was altogether a new kind of princess. No garden parties and floral dresses for her. Her look consisted of a silver minidress with skin-baring cut-outs along the bodice, strappy silver heels, and an oversized leather jacket to complete the look. 

While her mirror ball-inspired ensemble was the perfect choice for sitting front row at a fashion show, it was a bit out of bounds for a member of European royalty. With people around the world beginning to question the relevance of monarchy in our modern world, refraining from glitz and glamor could be read as a smart way for members of royalty to ingratiate themselves back into the public's good graces. With this political noise in the background, Princess Charlene's seductive gown is less of a style slay and more of a PR misstep.

What colors and patterns do you most associate with Christmas? If you live in the western part of the world, you might think of red and white with candy cane stripes, or if you're feeling fancy, maybe a light blue with snowflake patterns. However, for Charlene, Princess of Monaco, it seems that neutral tones and muted outdoorsy patterns are more her speed. 

While Charlene hasn't spoken publicly about this style choice, the outfit she wore to the Monegasque palace's annual Christmas party in December of 2020 was a bold enough statement in itself. The princess arrived at the event wearing a long black turtleneck under a bronze-colored kaftan with leaf and butterfly designs. She paired it with a sparkly gold face mask and — most surprising of all — a bold asymmetrical haircut. Before the event, the princess shaved half of her head. Experts told the Daily Mail that it seemed to be a deliberate attempt to rebel against royal expectations.

While the look was very on-brand for Charlene considering her past tomboy and punk rock-inspired looks, it felt a bit out of place with the otherwise jubilant and colorful vibe of the toy drive she was attending. In press photos released after the event, Princess Charlene's outfit is clearly in disharmony with the bright pinks, blues, and greens that make up the toy boxes on the shelves behind her. 

Prince Albert II and Princess Charlene are a strange pairing at the best of times. From the moment photos from their 2011 wedding were released showing Charlene wiping what looked like unhappy tears at the altar, rumors of friction and separation have plagued the royal couple. Over the years, Prince Albert's complicated relationships with his love children and awkward public moments with Princess Charlene have only added fuel to the tabloid fire. 

One such awkward outing occurred when Princess Charlene attended the 2018 Red Cross Gala in a gown completely uncoordinated with her husband's traditional ensemble. While Prince Albert wore a white tuxedo suit paired with black trousers and a crimson bowtie, his wife, who is 20 years his junior, wore an eye-catching metallic gown with a low-cut neckline that looked as if it was made out of medieval chainmail — or maybe fish scales? 

The dress smacks of something you might see on an experimental runway at New York Fashion Week rather than in the entryway of Monaco's Red Cross Gala. While it's undeniable that Princess Charlene looked stunning in the glittering gown, her aesthetic was out of sync with her husband's, whose classic suit looked as if it could have been taken right out of the 1940s,when Albert's great-grandfather first founded the charity ball. With links of metal chains lining the V-neck cut of Charlene's gown, it's clear that this hard rock number was not the best choice for the occasion. 

The Roman Catholic Church is an old institution — and we mean really old. In fact, the word "pope" was first used in the 4th century by Pope Siricius. And if you thought some European royals had long official titles, wait until you get a glance at some of the lengthier epithets the Roman Catholic Church's leader bears. Some of the pope's grander titles include Vicar of Jesus Christ, Supreme Pontiff of the Universal Church, and Metropolitan Archbishop of the Province of Rome.

With such a grandiose and storied history, it's no surprise that those who travel to Vatican City to meet the pope must adhere to a strict dress code. And yes, that even means royals. Traditionally, most female royals who meet the pope wear black lace. However, if you are a Catholic royal you possess something called "privilège du blanc," meaning that you are able to wear white in your meet and greet with the ol' Vicar of Jesus Christ.

Princess Charlene happens to be one of the select few women on the planet who are allowed to wear white when visiting the pope. And so, when Charlene met Pope Francis in 2016, she proudly donned an ivory dress with a cream-colored coat and a veil. However, her knees were also peeking out from her dress — a big no-no when it comes to greeting the head of the church.

Do you remember the naked dress trend? This was a phenomenon that started around the early 2010s that saw everyone from Beyoncé to Zoë Kravitz to Megan Fox to Emily Ratajkowski walking the red carpet donning super sheer gowns that left little to the imagination. With strategic peeks of skin and often some wisely placed gemstones over one's chest, these "naked" dresses earned the name because they gave the appearance that the celeb really was wearing nothing but their birthday suit. 

Often, these dresses included a lining that matched the wearer's skin tone; the look hammered home the illusion that the wearer was completely nude underneath. The trend has become so popular that some argue it has started to lose its shock factor. However, when Princess Charlene donned what could be considered a nude illusion dress at the 2013 Love Ball, she stood out from the other female attendees. As far as HuffPost was concerned, she managed to "out-glam" the host, model Natalia Vodianova.

The event was held in honor of Vodianova's Naked Heart Foundation. While it's possible that the princess chose this gown in honor of the foundation's name, the sultriness of her look eclipsed any sort of charitable celebration intended. With a strapless bodice in a pale blush color and a sheer overlay skirt that fanned out at the knees, there's no denying that this look matches the barely-there aesthetic of past nude illusion dresses. Depending on who you ask, it may be a bit too suggestive for a royal.