How Celebs Echo Diana’s Iconic Street Style

Who’d have thought dressing like a royal could be so comfortable? Beloved by Kendall Jenner, Bella Hadid and the rest of fashion royalty, a sweatshirt-bike-short combo was one of Diana’s go-to pairings. In 2022 this look couldn’t be more current with our love of elevated sportswear and effortlessly chic off-duty styling. The recipe for this simple yet effective outfit starts with a comfy, oversized sweater, snug black shorts and chunky white trainers as a sporty base. Finish off the look with luxe accessories like gold jewellery, leather handbags and a slick pair of shades for that preppy princess polish. 

Cowboy boots may not be the first thing that comes to mind when we think of Princess Diana but she really knew how to wear them. Celebs have followed in Diana’s (literal) footsteps as they use cowboy boots to offset casual looks with a nod to preppy, equestrian style. A simple switch of your favourite sneakers for a pair of boots can give even the comfiest ensemble a fashion-forward flourish. Lean further into the aesthetic with polos and blazers for that heritage Ralph Lauren aesthetic Princess Diana so seamlessly embodied.

The Princess of Wales’ rise to fame ran parallel with the upsurge of blazers and shoulder pads in women’s fashion, one after another we watched a young Diana Spencer pull off the power-dressing silhouettes of the 1980s with grace. Early on in her public life, Spencer’s blazers would come accompanied by the pussybow blouses and feminine cardigans typical of royal dress codes, but after her separation from Prince Charles, we saw a more independent Diana emerge and with it, a cooler, more laid-back wardrobe. Suddenly the princess’s blazers were layered over white tees and blue denim, delivering effortlessly chic ensembles that have maintained their appeal throughout the decades. Models like Kaia Gerber and Emily Ratajkowski have taken notes from this style ethos, often using similar boxy blazers to elevate informal looks.