Spanish actress Penelope Cruz decided she wanted to become an actress after watching Pedro Almodóvar’s cult rom-com Tie Me Up! Tie Me Down! in 1990. Two years later, she made her cinematic debut with her own cult flick, Jamón Jamón. Since, Penelope has gone on to forge a decades-long (and critically acclaimed) creative partnership with Almodóvar, himself, spanning 1999’s All About My Mother to Volver — which earned the actress an Oscar — and beyond. She’s starred in high-calibur Hollywood action flicks (Vanilla Sky) and Disney franchises (Pirates of the Caribbean) alike. Beyond cinema, she’s faced Chanel campaigns and even played eternal fashion icon Donatella Versace. In terms of her own personal style, Penelope’s singular look flourished around the turn-of-the-millennium. Rather than indulge the era’s most-worn trends (think Y2K’s hot pink micro minis, and diamante — although there is an incredible Chloé-by-Stella moment), Penelope championed a post-90s minimalism that took in slinky slip dresses, cashmere twinsets and pantsuits. Here, we take a look back at some of Penelope’s most iconic outfits of the 00s era.
At The Muse premiere, 1999
Actress Penelope Cruz made her movie debut in 1992 cult Spanish film Jamón Jamón, becoming an instant international sensation for both her beauty and acting chops. The actress followed up her acclaimed debut with roles in the 1992 Oscar-winning comedy-drama Belle Époque and Spanish director Pedro Almodóvar’s 1999 film All About My Mother, before making her Hollywood breakthrough in 2000. Here, a year before playing her star-making role in All The Pretty Horses, Penelope attends a red carpet ceremony wearing the look she’s best known for: the slinky slip dress.
At the Palm Springs International Film Festival, 2000
Penelope loved a slip dress moment. Into the Y2K era, the Spanish actress championed the 90s style staple, whether in slinky jersey or jewel tone satins. Here, to the Palm Springs Film Festival, Penelope wears a clingy red jersey take on her favoured look, complete with a wooly cover-up — another one of the actress’s signature pieces.
At the Golden Globes, 2000
As a teenager, Penelope became interested in acting after watching Almodóvar’s 1990 film Tie Me Up! Tie Me Down! Seven years later, she was cast in Almodóvar’s Live Flesh. The film marked the beginning of a two decade (and counting) long collaborative partnership between the duo. Penelope and Almodóvar’s second project All About My Mother earned the director the Golden Globe for Best Foreign Language Film. Here, Penelope, the film’s breakout star, attends the awards ceremony alongside the director, wearing her favoured slip dress layered beneath a diaphanous chiffon shawl.
PHOTO BY JIM RUYMEN/AFP VIA GETTY IMAGES
At an Academy Awards party, 2000
What’s Y2K fashion without a little bit of glitz? Here, to a dinner reception held before the 2000 Academy Awards, Penelope wears a diamante-encrusted halter top and low-rise trouser combo designed by none other than Stella McCartney (and right-hand woman Phoebe Philo) for Chloé’s iconic SS00 collection.
PHOTO BY KEVIN MAZUR/WIREIMAGE
At the Academy Awards, 2000
In addition to a Golden Globe, All About My Mother won the Academy Award for Best Foreign Language Film. To the ceremony, Penelope followed up her Golden Globes slip dress with a topaz blue satin strapless gown and an equally ethereal chiffon shawl.
PHOTO BY FRANK MICELOTTA ARCHIVE/GETTY IMAGES
At the Cannes Film Festival, 2000
Between making Hollywood breakout turns in 2000’s All The Pretty Horses and 2001’s Vanilla Sky, Penelope starred in the lesser known American film Woman On Top. In the fantastical romantic drama, Penelope plays Isabella, a renowned chef plagued by chronic motion sickness. Attending the film’s Cannes premiere alongside director Fina Torres, the actress wore a monochromatic twinset-and-pencil-skirt look paired with her trusty Prada sandals.
PHOTO BY CARLOS ALVAREZ/GETTY IMAGES
At a Ralph Lauren press conference, 2002
By 2002, ‘the tie’ had become a full-blown Y2K womenswear trend (thanks Avril Lavigne!). Here, however, Penelope puts her own sophisticated spin on the look in full three-piece suiting by Ralph Lauren. A perfectly unconventional Y2K look, fit for the one of the era’s most underrated style heroes.
