Times Princess Charlene Has Channeled Grace Kelly's Iconic Looks

Princess Charlene of Monaco has faced sky-high expectations since the day she married the principality's sovereign, Prince Albert, in 2011. The last woman to wear the Monégasque crown was the Hollywood legend and fashion icon Princess Grace Kelly. Although Princess Charlene and Grace Kelly certainly shared similar struggles in private, there is no comparison between the way the two princesses were perceived by the public. While Grace was a wildly famous movie star before she became a royal, Charlene's background as a professional athlete and a commoner left Monaco's high society with its fair share of doubts. Grace had, essentially, left Charlene with big shoes to fill.

Commenting on this point in a conversation published in the Express in 2021, royal expert Coryne Hall explained, "It's a hard act for Charlene to follow, really, because she is always going to have these comparisons with Princess Grace." This reality has put a certain degree of pressure on Charlene; however, she has done her best to lean into it. Rather than avoiding comparisons to Grace altogether, Charlene has often embraced her late mother-in-law's fashion choices — keeping her iconic sense of style alive. Indeed, many of the most alluring outfits that Princess Charlene has ever worn actually mirror some of Grace's most striking ensembles. By paying homage to Grace's fashion choices — whether deliberatley or not — Charlene has been able to step more elegantly into her princess role. She has also, consequently, established herself as a fashion icon in her own right.

Nothing screams "movie star" like a big pair of shades — and Princess Grace Kelly of Monaco knew it. The Academy Award-winning actor made the shocking decision to ditch Tinseltown for good in order to marry Prince Rainier of Monaco in 1956. That very year, Grace was photographed on her way to go sailing in the principality, and, unlike her contemporaries in countries like Great Britain (think Queen Elizabeth II), she looked very California cool in a giant pair of black sunglasses. 

The Hollywood legend's eyewear choice has continued to inspire designers to this day. As Freddie Elborne of the brand Monc told The Telegraph four decades after Grace Kelly's death, "Every summer, a new sought-after variation of this design will materialize, but it's the women such as Grace Kelly and Marilyn Monroe who have given this style its timeless allure."

Grace's daughter-in-law, Princess Charlene, has embraced this particular accessory. During a meeting with Pope Leo XIV in 2026, Charlene donned the white attire traditionally required for Catholic sovereigns, per the Vatican's dress code. That said, Charlene deviated slightly from protocol by wearing a massive pair of black shades. While it would be highly unusual for another princess — think Princess Catherine of Wales or Princess Leonor of Spain — to sport sunglasses in such a high-profile meeting, Charlene channeled Grace, brimming with Hollywood glamour. 

Princess Charlene and Princess Grace Kelly may have both looked fantastic in sunglasses, but the stylistic similarities between the two women don't end there. Over the years, Charlene and Grace have sported dresses with comparable colors and cuts. At times, it's hard to know whether Charlene is purposefully paying tribute to her late mother-in-law or simply leaning into the trends that Grace Kelly so brilliantly established long ago. Nevertheless, Charlene has been known to rock the styles that Grace popularized in the past.

This was clear in September 2025 when Charlene attended the Ballon D'Or awards ceremony in Paris. On this occasion, she sported a stunning white floor-length gown. With its high neckline and long skirt, the piece immediately called to mind a similar dress that Grace had worn on the set of the movie "High Society" decades before. While Charlene's dress boasted long sleeves, Grace's actually bared her arms, creating something more of a Greco-Roman look.

Charlene's choice of dress highlighted the physical similarities she shared with her late mother-in-law. Both princesses are known for their blond hair, blue eyes, and fair complexion. At the Balloon D'Or ceremony, Charlene leaned into this parallel a little more — even curling her bangs the same way that Grace once did. While she did ultimately make the style her own, Charlene could not help but invoke Grace on the day of the event.

Princess Grace Kelly and Princess Charlene have a lot in common fashion-wise, even though they have taken slightly different approaches to styling. While Grace was largely known for her signature blond hair, Princess Charlene has made headlines based on her iconic (and disastrous) royal hair transformations. Despite this, when 2023 saw a brunette Charlene step out at a Monaco Grand Prix dinner, royal fans could not help but compare her to Grace Kelly. The princess' dark pixie cut did nothing to diminish that her $11,000 Valentino dress looked like the modern version of a frock that Grace had worn on the set of "Rear Window" decades earlier.

Charlene's stunning black and white dress featured bold lines and a bold silhouette. The asymmetric neckline and sleeve was just the right amount of edge, and the white and black skirt truly popped. Ultimately, though, the piece recalled Grace's black and white "Rear Window" dress. With a dark top and white skirt, this vintage frock featured same contrasting color scheme that would inspire Charlene years later. And while the modern princess' asymmetric dress bared one shoulder, her predecessor's dress featured slightly off-the-shoulder sleeves. These differences show that Charlene's tendency to find inspiration in Grace's wardrobe has not prevented her from transforming the actor's style choices into fashion statements of her own. 

Both Princess Grace Kelly and Princess Charlene came to understand that being a princess is not easy. Because both women were born into families of commoners, they both found that adjusting to royal life had its fair share of challenges. Among those was learning to balance "normal" parenting practices with royal wardrobe expectations. (Remember, royal families traditionally hire nannies to care for their children). Interestingly, Grace and Charlene both seemed to have found a middle ground in the traditional button-up shirt.

Indeed, on a school visit with her children, Princess Caroline and Prince Albert, Grace wore a button-up collared shirt and belted skirt. The ensemble really hit the mark. While informal enough for domestic duties, it still exuded a sense of regal energy. No one could accuse Grace of appearing overly informal; however, she still seemed relaxed enough to provide care for her little ones.

Decades later, Charlene visited Rust, Germany, with her twins, Prince Jacques and Princess Gabriella. On this occasion, the sovereign's wife was photographed wearing almost the exact outfit that Grace had once worn. Donning a button-up collared dress with a belted skirt, Charlene was Grace's spitting image. Increasing the resemblance even further, Charlene paired her outfit with a casual updo — just as Grace had done years before. The episode demonstrates Grace's prevailing influence in royal fashion as well as her permanent impact on Monégasque royal protocol.

It's hardly a secret that Princess Charlene and Princess Grace Kelly have looked amazing while wearing similar outfits. Their specialty? Dresses that combine dramatic cuts with cool colors. Back in 1955, Grace proved this point to be true, wearing a powder blue dress with a dramatic double-winged cape. Not only did this shade complement her skin tone, but it also made her eyes pop. Ever the royal woman, Grace made her cape look like a simple accessory rather than the star of the show.

Fascinatingly, Charlene sported a similar style at the 2026 Rose Ball. Opting for an icy grey Elie Saab gown, Charlene leaned into the same cool color palette that once looked so good on her late mother-in-law — and made it her own. Whereas Grace had once worn a full-blown cape with her dress, Charlene selected an asymmetrical gown with a single cape sleeve. The result was just as dramatic as something that Grace would have worn in Hollywood, although that was kind of the point. The theme of the 2026 Rose Ball theme was galaxy by Christian Louboutin, and Charlene intended to shine. Covered in sparkles and a sheer off-the-shoulder cape, Charlene looked like the personification of the Milky Way herself. She looked so regal in her attire that Princess Grace would have certainly been proud.

They say that green is the color of envy, but it's hard to imagine Princess Grace Kelly or Princess Charlene coveting anything at all. The two women had riches for days (Princess Charlene has the most expensive wardrobe of all the royal women in Europe), and they could pull off a wide range of colors — including bright green. In 1954, Grace stunned in a strapless emerald green gown that she wore for the occasion of St. Patrick's Day. With little green sparkles embroidered onto the top, the piece could have easily seemed a bit over-the-top. Grace, however, wore it beautifully, looking natural in the dress. In one shot, she was captured clutching a mug of coffee in both hands, while a newspaper was open on her lap. She looked both perfectly cozy and like the picture of elegance in the voluminous ball gown.

When Charlene wore an emerald dress of her own to the 61st Monte Carlo TV Festival in 2022, she replicated Grace's casual confidence. Sporting the same attention-grabbing color that had once graced her late mother-in-law's wardrobe, Charlene glimmered like a diamond — or should we say an emerald? She selected an asymmetrical cut that contrasted significantly with the sweetheart neckline that Grace had previously worn. However, her breezy confidence and clear comfort in the extra bold dress reminded us of Grace's effortless glamour. 

Princess Charlene sure has worn a lot of incredible capes, but she's not the first member of the Monégasque royal family to do so. Princess Grace Kelly was often photographed wearing dramatic capes to parties and galas. At the Night of 100 Stars benefit gala in 1982, Grace stunned in a deep indigo cape that married Hollywood drama with royal flair. While the dramatic ensemble might've pulled too much focus if just about anyone else wore it, such was not the case for Grace. She wasn't just a film icon; she was also a bona fide princess. Her look established a sense of royal status — one that would later inspire Charlene to stand out from the crowds, as well.

Over the years, Charlene has been known to follow in her late mother-in-law's cape-wearing footprints. This was evident in 2017 when she celebrated Christmas in a bright red coat cape. As she strolled out in front of members of the public, Charlene looked like she had come straight to Monaco from the North Pole. Her cape was a pure statement piece — fun and festive yet so dramatically royal that one could not even begin to question her status.

Two years later, Charlene wore another cape, this time to the Red Cross Ball. The green floor-length feature was sewn into her dress of the same color, adding extra flair. Once again, Charlene used one of Hollywood's favorite royal symbols to denote her status — and it totally worked. 

Although Princess Grace Kelly and Princess Charlene have been known for wearing capes to cover up, that does not mean they ruled out baring their shoulders. On the contrary, Grace and Charlene have both showed off their shoulders on numerous occasions, even accentuating this feature by wearing halter dresses. Charlene aced this look at the 2026 Red Cross Ball, where she stunned in a gold dress by Elie Saab. The piece drew attention to Charlene's shoulders with a neckline that resembled an Old Hollywood scarf. Given that Grace once wore similar styles, it's hard to believe that Charlene didn't get a bit of inspiration from her predecessor.

Indeed, back in the 1950s, as her career was blowing up, Grace posed for some lovely headshots. In one of the photos, she sported a periwinkle blue dress that boasted a cut not dissimilar from Charlene's Elie Saab piece. With a criss-cross halter neckline, the dress recalled a certain type of Old Hollywood scarf. It also showed off Grace's shoulders beautifully, all while elongating her neck. The similarity between Grace's dress and Charlene's just goes to show that some dresses never really go out of style. The fact that Charlene sought inspiration in one of Grace's best outfits also stands as proof of the late princess' status as a veritable fashion icon.

Princess Grace Kelly's fashion choices weren't always traditionally feminine — a fact that has not escaped her daughter-in-law, Princess Charlene. Although Grace has long been lauded as a 20th century symbol of femininity, the actor also enjoyed wearing slacks on occasion. This was evident shortly before she married Prince Rainier of Monaco. In the lead-up to her royal wedding, Grace posed for some photographs in casual wear. Sporting a collared shirt, high-waisted trousers, and a belt, the actor looked far more like the girl next door than the future Princess of Monaco.

Years later, Charlene emulated Grace's iconic look at the Princess Grace Awards in Monaco. Dressed in high-waisted slacks and a collared shirt, Charlene's ensemble seemed to pay tribute to the late princess. As per usual, however, Charlene added her own sartorial touches to the outfit, opting for a pair of black suspenders in lieu of a thick belt. She also dressed the casual wear up a bit by adding a blazer — in apparent recognition of the fact that she was attending a formal event. 

Charlene's outfit challenged notions surrounding what sort of clothing a princess can or cannot wear, while still honoring Grace. This move was very in line with Charlene's personality. After all, unlike many royal women, Charlene is a self-proclaimed tomboy with a decades-long history of preferring slacks to skirts. Donning trousers à la Grace was right up her alley.

Both Princess Grace Kelly and Princess Charlene have looked phenomenal in blue, but the princesses' shared love of the traditional royal color goes beyond the actual shade. Both Grace and Charlene have shown a penchant for wearing dresses that feature transparent blue fabric. While filming the 1955 movie "To Catch a Thief," Grace donned a blue gown accompanied by a sheer blue wrap-around. The look — which had been created just for her by designer Edith Head — did a beautiful job of creating an air of elegance and mystery around Grace. In 2025, Charlene stepped into a similar gown for the Red Cross Ball — and yes, she positively rocked the timeless look.

At the event, Charlene was an absolute vision. Her own periwinkle blue dress was dreamy yet regal. As with Grace's outfit, Charlene's embodied a sense of mystery, thanks to the lovely sheer blue cape that was draped over her arms. Interestingly, this particular outfit seemed like an open tribute to Grace's fashion choices, due to the way that Charlene styled it. With her hair swept into an updo that was almost identical to Grace's and her makeup applied in the same fashion as her late mother-in-law's, Charlene looked like a modern Grace Kelly. Dare we say, she pulled off the look with grace.