On November 11 2024, Hollywood heartthrob and acting legend Leonardo DiCaprio celebrates his 50th birthday.
When it comes to red carpet elegance, casual cool and It-boy dressing, few stars are as suave as Leo. From his heartthrob days in Romeo & Juliet and Titanic, making him one of the most coveted young actors in cinematic history, to his Academy Award-winning performances in The Revenant and The Wolf of Wall Street, Leonardo has not only cemented his reputation with his talent on-screen but has also solidified his status as one of the globe's ultimate style icons (we'll leave it up to you to discuss his girlfriend roster...)
It was his 1990s-style agenda that captured the hearts of people around the globe, a time when the media was becoming more focused on celebrity culture, and the youth demographic had more access to films and entertainment content. His good looks, charming persona and undeniable talent hit at the perfect time. His mid-length sweepy hair combined with his piercing blue eyes and effortlessly fashion-forward wardrobe, shot him to dreamboat status.
Whether he's wearing a classic tuxedo, wearing the biggest trends of his time, or oozing laid-back Los Angeles cool, Leo's fashion moments never ever fail. As the icon celebrates his milestone birthday, we take a closer look at his most memorable sartorial moments over the years.
© Jeff KravitzTJ Martell Music Event, 1989
15-year-old Leo epitomised late-80s cool in an orange patterned shirt that boys in East London would be fighting over on Depop in 2024.
© Vinnie ZuffanteAnnual National Board of Review of Motion Pictures Awards, 1994
Leonardo was a huge fan of the collarless shirt in the 90s. Here stepping out alongside Gwenyth Paltrow, he paired it with a navy corduroy suit.
© Catherine McGannNew York, 1995
A fresh-faced Leo posed for a photograph in New York aged 21, wearing a light-coloured waffle shirt that screamed 90s cool. Little did he know in the two years to follow with the release of Romeo & Juliet (1996) and Titanic (1997), his life was about to change forever...
© mikel robertsDouble Denim, 1995
In one of his most iconic photographs of all time, Leonardo posed in 1995 in a double denim off-duty look. The pièce de résistance? One single lick of hair cascading over the front of his face.
© Rose Hartman'The Basketball Diaries' premiere, 1995
Rocking up to the event with the equally as swoon-worthy Mark Wahlberg, Leo perfected 90s pinstripes in a vest and jacket combo, layered with a satin shirt.
© Patrick McMullanSeptember 15, 1995
Honestly? this burgundy leather jacket would slot perfectly into the wardrobes of It-girls and influencers in 2024. Obsessed.
© Steve GranitzRomeo & Juliet Los Angeles Premiere,1996
Attending the premiere of one of the films that defined his career, Leo stepped out with his then-girlfriend Kristen Zang wearing a navy suit with a satin sheen, paired with a crisp white shirt with a chunky collar. A special shoutout to Kristen's Burberry midi, too.
© Vince BucciCourtside Cool, 2004
Off the red carpet and into the Staples Center, Leo sat on the infamous front row of an LA Lakers game. He wore a black bomber jacket, a grey striped shirt, mid-wash jeans and a pair of Nike Shox. A laidback cap finished off his high-low dressing look.
© Isaac BrekkenCinemaCon, 2018
Jumping ahead a couple of decades, Leo proved his style is still as swoon-worthy as ever. He oozed cool in a grey suede bomber jacket and crisp white trainers.
© Emma McIntyreAcademy Museum of Motion Pictures, 2023
One look he's never ever got wrong? A classic black tie tux. He opted for a Gucci black satin shawl lapel tuxedo in2023, proving his penchant for enduring style on the red carpet.
