It will come as no surprise that the late Princess Diana remains the world’s ultimate style icon, even twenty-eight years after her passing. Her natural sense of style is as prolific today as it was during her years as a working royal. Arguably the world’s first true fashion influencer, Diana inspired countless individuals with her innovative approach to fashion trends and her pioneering influence.
As a fashion editor, I adore many of her iconic looks—from the famous ‘revenge dress’ to pastel suits and Gucci handbags. However, it’s her casual ensembles that truly capture the essence of her style. Diana’s wardrobe ranged from oversized sweaters to the directional moment she tucked jogging bottoms into high-heeled boots—a choice that was ahead of its time.
One memorable look was in 1989, when Diana was photographed dropping off Prince William and Prince Harry at Wetherby School. Her outfit epitomized elevated sportswear with an elegant twist. She teamed off-white joggers with a classic white T-shirt and super slouchy terracotta boots—a combination that shouldn’t work, but absolutely does. Completing the look with a pinstripe navy blazer and a cap, Diana showcased a style that feels as fresh today as it did then.
And it’s not just a relic of the past! Fashion influencer Katie Impey, known as @themumlife_styled on Instagram, recently published her own take on this iconic trend. She expertly styled blazers and scarves with joggers and boots, sharing side-by-side photos with Diana’s original look. Katie commented:
> “Big Fan of boots with joggers, HUGE in fact, always have been, but swipe for the OG influence.”
We spoke to Katie about her recreation of Diana’s outfit, and she explained to HELLO!:
> “There’s a real nonchalance to pairing boots with joggers, and it makes for the perfect off-duty, weekend look—casual but still feels effortlessly put together. I like to go baggy with the joggers for a balloon effect, add a blazer and baseball cap for an added element of smart casual.”
### Princess Diana: Queen of Sporty Chic
Princess Diana’s influence extended to athletic-inspired looks as well. In 1995, she was famously pictured leaving Chelsea Harbour Club gym, channeling ultimate gym bunny style. Diana teamed orange cycling shorts with a close-fit boxy sweatshirt, trainers, and a sleek black handbag. The look was impossibly polished, and fans fell in love with her dressed-down ensemble.
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## More Royal Style
– **I’m a fashion editor and Princess Diana is still my ultimate style icon 28 years on:** Prince William and Prince Harry’s mother will be forever remembered for her elite sense of style, from designer bags named after her to Catherine Walker suits. She was the queen of fashion.
– **Princess Diana’s rugby top is the 2025 autumn trend you should be investing in:** Rugby tops and shirts are huge this autumn-winter, and Diana led this style revival, first wearing one in 1997.
– **Princess Kate: Queen of the Pussy Bow:** The mother of Prince George, Princess Charlotte, and Princess Louis often champions the super flattering pussy bow blouse.
– **This chic AW25 supermarket collection has an outfit for every event in your festive calendar:** Abbey Clancy curates another stellar edit for F&F at Tesco, with prices from just £10.
– **Duchess Sophie subtly ‘tells a story’ with a silky £3k chocolate Armani gown:** The Duchess wowed at the Awareness Foundation dinner at the Lansdowne Club in London.
– **Queen Camilla makes £10k skull addition to outfit borrowed from late Queen:** Camilla wore a sentimental brooch for the 97th annual Field of Remembrance at Westminster Abbey.
– **Pippa Middleton’s forgotten spin on the ‘naked’ dress:** At Wimbledon 2017, the Princess of Wales’ sister opted for a daring dress covered in cut-outs.
– **Zara Tindall’s rarely-seen Mulberry ‘Bayswater’ bag:** Princess Anne’s daughter made a statement with the vibrant red bag at the Cheltenham Festival in 2011.
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Princess Diana’s influence on fashion endures. From glamorous eveningwear to elevated sportswear, her legacy lives on in today’s trends—proving she truly is the OG style icon for the ages.
https://www.hellomagazine.com/fashion/royal-style/866358/princess-diana-wearing-joggers-and-high-heel-boots-for-2025/
