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Hailey Bieber has made no secret of the fact that she looks to Princess Diana for style inspiration – increasingly turning to her signature low-key looks when putting together her casual ensembles.
While many celebrities have drawn inspiration from Diana’s glamorous gowns, tiaras and show-stopping dresses, the wife of singer Justin Bieber has carved out a niche by focusing on Diana’s relaxed, off-duty wardrobe.
Who could forget those iconic photos of Princess Diana running around town in a baggy Virgin Fly Atlantic sweater, peach bike shorts, and chunky runners?
Hailey certainly remembers – and the trendsetting model has put her own millennial twist on the look.
The 28-year-old has spoken openly about her admiration for the late royal’s style and, in 2019, she praised Diana for ‘leaving behind such an iconic fashion and style legacy’.
Channelling Princess Diana’s sporty style, Hailey Bieber dressed down in Los Angeles in 2024, sporting the late royal’s signature off-duty pairing, an oversized top worn over super-short cycling shorts. The model’s look comprised a Saint Laurent jacket and Alo shorts, while Diana wore her famous Virgin Fly Atlantic sweater to the gym in 1995 which was gifted to her by the airline’s founder Richard Branson and was later auctioned for more than £40,000
Putting her own millennial twist on the late Princess Diana’s iconic off-duty looks, Hailey Bieber stepped out to buy a coffee in Beverly Hills in 2019. She kept it casual in an oversized grey Cornell University sweatshirt. Her top mirrored the Harvard design which Diana wore in 1997 while on a run
Hailing Diana as an inspiration, Hailey Bieber shares the late princess’s love of letterman jackets with this vintage Chicago Bulls satin version when out and about in 2019. It was similar to Diana’s iconic custom-made Philadelphia Eagles jacket which was given to her by broadcaster Jack Edelstein
One of Diana’s most iconic looks which Hailey has made her own is the athleisure ensemble.
Cycling shorts, an oversized university sweatshirt and sneakers have become the recipe for a modern-day Princess Diana moment.
In the late 1980s and early 1990s, Diana was often spotted in this combination, elevating what could have been a purely practical outfit with luxury accessories.
Diana’s understated Gucci Bamboo tote has found a parallel in Hailey’s collection of designer arm candy, from Bottega Veneta clutches to Prada shoulder bags.
Mirroring outfits made famous by the late princess, Hailey has taken a page straight out of Diana’s iconic style playbook, seamlessly blending vintage inspiration with her signature contemporary edge.
Diana had an unmatched ability to mix high fashion with casual, effortless charm, and Hailey has embraced that same ethos, bringing the princess’ iconic casual looks back to life for a new generation.
With modern alterations added to Diana’s style repertoire of oversized blazers, cycling shorts and high-waisted jeans, Bieber channels Diana’s sporty-meets-sophisticated vibe.
Diana famously wore a British Lung Foundation sweater to the Guards Polo Club in Windsor in 1988 which was layered under a blazer and paired with cowboy boots and a cap. In 2019, Hailey took inspiration from the late princess for a Vogue Paris photoshoot by wearing a near- identical outfit
During the Easter holidays in 1993, Princess Diana treated her sons to a day out at Thorpe Park in Surrey, when she dressed casually in a Hard Rock Cafe black leather jacket, black jeans and low-heeled boots. Hailey emulated the princess’ athleisure look with an oversized 23 Lux vintage jacket when she stepped out in New York City in January 2023
Effortlessly channelling Diana’s signature pared-back aesthetic in a Polo Ralph Lauren red puffer jacket, Hailey Bieber wrapped up for an alpine break in Aspen, Colorado, in 2023. The look is reminiscent of one the princess sported during a ski trip to Austria in 1994
Princess Diana championed the double denim trend during a ski trip to Lech, Austria, in 1993. Following in her fashionable footsteps, Hailey paired a jacket by The Row with Levi jeans when stopped off for a coffee in Los Angeles in 2019
Fast-forward to the 2020s and Hailey has embraced this look wholeheartedly, often photographed in her own version of Diana’s sporty chic style.
From gym-ready outfits to paparazzi-chic streetwear, Hailey’s wardrobe regularly pays homage to Diana in the most stylish ways.
Diana had an ability to make even the simplest outfits look chic and Hailey’s approach is similar. She takes classic pieces and makes them feel fresh, modern, and aspirational.
These quintessentially Diana combinations feel like a love letter to Diana’s enduring style. Yet she’s not simply copying looks, Hailey reinvents them, proving that true style is timeless.
She is constantly paying tribute to a woman who redefined what it meant to be a modern royal.
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