6 Historic Monaco Ball looks

Grace Kelly in red chiffon. Princess Caroline with an orchid tucked into her hair. Princess Charlene in a crystal-covered Versace gown. For more than seven decades, the Monaco Red Cross Ball has produced some of the Grimaldi family’s most memorable fashion moments.

Held each summer since 1948, the glamorous charity gala brings Monaco’s royal family together with an international guest list. Over the years, Lionel Richie, Karl Lagerfeld and Elizabeth Taylor have all attended. In 1959, King Juan Carlos I was seated beside Grace Kelly herself.

The ball has also offered a revealing look at the evolution of royal style across generations. Grace, Caroline, Stéphanie, Charlene and Charlotte Casiraghi have each brought a distinct point of view to the event, from classic Hollywood glamour to bold silhouettes and modern couture.

Here, the fashion editors at ¡HOLA! revisit six standout looks that made an impact when they first appeared and remain just as memorable today. Among them are Grace Kelly’s flowing red gown, Caroline’s unmistakably 1970s beauty look, and Charlotte Casiraghi’s daring Chanel minidress.

1. Grace Kelly in 1976

The American actress, then 47 and married to Prince Rainier III, arrived at the Red Cross Ball in a spectacular red chiffon gown. The long, ethereal design featured an attached cape, which she complemented with a magnificent Art Deco diamond necklace. The photograph remains one of the earliest surviving color images of the former actress and Princess of Monaco at the gala.

2. Princess Caroline of Monaco’s Unforgettable 1974 Look

At just 17, Grace Kelly’s daughter still maintained a relatively low profile within Monaco’s royal family. Her appearance at the Red Cross Ball, however, helped usher in a more prominent role at official engagements and marked an early step in her rise as a fashion icon.

Rather than echo her mother’s classic glamour, Caroline chose a simple white dress with subtle raised embroidery across the bodice. The true focal point, however, was her beauty look. An oversized orchid tucked into her hair gave the ensemble its dramatic flourish, while heavily defined lashes and electric blue eyeliner captured the spirit of the 1970s.

3. Princess Caroline’s Elegant Minimalism in 2004

“This is a look that will always work, even more than two decades after the princess wore it. That is the power of a black slip dress: its timelessness,” says Cristina González, a fashion editor at ¡HOLA!.

No retrospective would be complete without the understated gown Princess Caroline wore in 2004. The sleek black design required little more than gold jewelry to make it feel polished and complete.

4. Princess Stéphanie of Monaco at Her Most Daring

“She was the rebellious princess, the one who broke the rules and said no when everyone expected her to say yes. Her life, shaped by tragedy, media scrutiny and a fiercely guarded sense of freedom, has always been reflected in the way she dresses,” says ¡HOLA! fashion editor Miriam Núñez del Bosque.

Stéphanie’s daring choice for the 2004 gala made that rebellious streak unmistakable. She challenged traditional standards of royal elegance by partially baring her midriff in a cutout gown with a plunging V-neckline. The dress also showcased the athletic physique that had drawn criticism in the press at the time.

5. The Dress That Nodded to Princess Charlene’s Swimming Career

In 2018, Princess Charlene chose a dramatic Atelier Versace Haute Couture gown. The mermaid silhouette featured a blue ombré effect and was covered in Swarovski crystals arranged to resemble tiny scales. The intricate embroidery evoked both the geometric elegance of Art Deco and the lavish glamour of The Great Gatsby.

“The gown also stood out for its unusual necklines. The V-shaped front was embellished with strands of tiny crystals, while similar detailing cascaded vertically down the back,” recalls Paula Callejo, a fashion editor at ¡HOLA!

The aquatic motif was widely interpreted as a nod to Charlene’s past as an Olympic swimmer. Knowing that a statement gown needs little competition, she completed the look with understated jewelry and a single ear cuff.

6. Charlotte Casiraghi in a Metallic Minidress in 2021

Although she regularly attends other events in Monaco, Princess Caroline’s daughter rarely appears at the Red Cross Ball. Still, ¡HOLA! fashion editor in chief Luis Javier Merino considers her 2021 ensemble one of the gala’s standout looks.

“It was a metallic design with ruffles and braided trim from Chanel’s Resort 2021 collection. She paired it with peep-toe shoes and a Half Moon clutch from the same fashion house,” he explains.

The ensemble combined the elegance Charlotte inherited from her mother with the rebellious spirit of her aunt. Its unusually short hemline made it a particularly bold choice for such a formal occasion.