Outdated Outfits Princess Charlene Wore That Had Everyone Cringing

Even before she married Prince Albert of Monaco in 2011, Princess Charlene's fashion was coming under the international microscope — because there's nothing royal watchers like more than a new outfit to admire ... or admonish. While she has certainly scored a bevy of hits with stunning gowns at royal affairs, Princess Charlene has had some memorable fashion misses along the way, too.

Whether these ensembles break royal protocol is up for debate in some cases, but what we do know is that they fall into the category of outdated and cringeworthy. Not to worry, she's in good company. Plenty of royals have stumbled on occasion, including Catherine, Princess of Wales' fair share of passé fashion moments, and her sister-in-law Meghan Markle's occasional dated duds. 

It's hard to be on point all the time, especially when photographers consistently document your life. The Princess of Monaco may wish the photogs had missed some of her more outdated looks.

Back in the 2000s, the future princess was simply known as Charlene Wittstock, a swimming champion from Zimbabwe and South Africa. That is, in fact, how she met the Prince of Monaco: at a swimming competition in Monaco in 2000. They made their first official bow as a couple in 2006 and Charlene was suddenly thrust into the limelight with all her choices under scrutiny, especially her fashion ones.

At a cocktail party at the 2007 Monte Carlo Television Festival, Charlene wore a look that screams 2000, meaning it was a few years past its prime even back then. The lingerie-inspired empire waist top worn over a silky camisole was a favorite of the Y2K era, especially for evenings out. Party girls would pair them with bootcut jeans or black pants, but here, Wittstock went for a knee-length black skirt. Another sign of the times: The black clutch. Everyone carried a clutch (and wondered where to put it when you sat at a restaurant table). Also notable are her lack of accessories other than a very simple bracelet on her right wrist. Dangly chandelier earrings would've been apropos in this era, but obviously Charlene skipped that trend. 

The Grimaldis (the surname of the royal family in Monaco) have a tradition of handing out gifts to local children each December. As expected, Princess Charlene always dresses for the occasion. One year she wore a black sweater and red plaid skirt; another she donned a red fisherman-knit sweater and black jacket; and at another event she wore wide-leg trousers, a white button-up top, and beautiful thigh-length red pea coat.

One of her looks, worn in 2017, seemed a bit out of place for the time. On the top, she wore a red cape — fabulous in every regard. But on the bottom, she had leggings and heeled boots, reminiscent of jodhpurs and riding boots. This combination, which Coco Chanel made stylish for women outside of the horse-riding arena in the 1920s, had a resurgence in the '80s and '90s thanks to Ralph Lauren. However, not many fashion-forward people were wearing the look in 2017, especially not with heeled boots instead of flat. That being said, Charlene should definitely revisit the look in the 2020s. Back in June 2024, Kendall Jenner and Gigi Hadid wore the combo at a Vogue World: Paris fashion show, moving equestrian flare back to the fashion forefront.

Since its debut in 1929, the Monaco Grand Prix, the Formula One race held through the streets of the principality, has been one of the biggest events on the royals' schedule. And though it's a sports event, it is known as one of the most glamorous events in athletics, and certainly the most glamorous in car racing, with celebrities and glitterati descending on Monaco for the race and the accompanying parties.

Despite all the attention on the event, where Charlene hands the top three drivers their trophies, she's donned some of her strangest outfits to the prize-giving ceremony. In May 2019 she wore an asymmetrical mandarin-collared tunic over pink pants. We're not sure what she was going for here. Edgy flamingo? Unfortunately, the dress-over-pants look had a short-lived moment in early 2000s. Plus, the cheongsam-esque top was a fixture of the grunge-era '90s in western cultures, making it a miss for 2019 Monaco.

Prince Albert and Princess Charlene were of course among royals invited to King Charles III's 2023 coronation. Sadly, she also made the list of worst dressed at the coronation ceremony. This is a woman that designer Karl Lagerfeld deemed would be a global fashion icon (according to People). But at the May 2023 event, she didn't live up to the moniker. For starters, there was the cream suit, with a bit of a stodgy 1980s vibe. Was the addition of the buttons that didn't align meant to add some edge to the look? It didn't work. Then there's the sash situation. Charlene's broad shoulders, which naturally helped her swimming career, look even wider with this scarf draped across them. Not only that, but the cream nylons also looked like they belonged in the last century. Sadly, this wasn't to be her last hosiery offense.

Monaco's princess is stunning and deserves to deliver better than this, which will be emblazoned forever as one of her worst looks.

Another big day on the Grimaldi's social calendar is the annual National Day of Monaco in November, to celebrate the country. For the 2024 celebration at the palace, Princess Charlene wore a lilac suit with dark hose and pumps.

Though there are elements of Princess Charlene's look that work, as a whole, it's a dated pass. Let's start with the fascinator. Why is she wearing it? She's not in Great Britain or at a horse race. It was out of place here. Then there was the lilac suit. The pale purple hue has had brief spurts of popularity, but this is a distinct color trend from the 1990s, automatically dating the look. But the biggest offender of the ensemble are the black nylons and shoes. Why wear nylons at all? And the black is so stark compared with the pastel outfit. It gives off a mod '60s aesthetic, again, dating the look. Instead, she could've kept it simple with a pair of neutral heels and foregone the hosiery. And in case you're thinking she's wearing the hose to adhere to regal rules, we doubt it. More than once, Princess Charlene has broken with royal protocol.