In 2024, Penélope Cruz and Chanel are as inseparable as the two C’s interlacing Chanel’s logo. Cruz’s brand ambassadorship might have become official in 2018, but her relationship with the French luxury house began as early as 1999 when she attended her first Chanel show. Over the years, she developed a close friendship with Chanel’s longtime creative director Karl Lagerfeld, later becoming one of his muses and then the co-chair of the 2023 Met Gala, themed “Karl Lagerfeld: A Line of Beauty” to honour Lagerfeld’s enduring legacy. These days, Cruz wears Chanel’s bouclé tweed, romantic laces or iconic bows to almost every event — very fitting for Chanel’s self-proclaimed biggest fan.

Dialling back to the beginning of her career, Cruz leaned into a more minimalistic aesthetic, ranging from a red slip dress at the 11th Palm Springs International Film Festival in 2000, to a strapless baby blue Dior haute couture gown at the amfAR Party in 2005. And while open necklines and elegant gowns have always been favoured, she has never shied away from switching into mannish suits instead, be it the boxy black set in 2001 or the sleek Giorgio Armani suit worn to the “On The Fringe” premier in 2022. One word to summarise Cruz’s style? Timeless — true a quarter of a century ago and true still.