“There’s a Diana for every mood,” star of The Crown Emma Corrin once mused of the wardrobe pointers she picked up while playing the Princess of Wales. “She has a take on every aspect of what you might want to wear; she really is the ultimate style icon.” While Lady Di’s twists on traditional formal wear as a senior royal, and her school-run style as a mother to Princes William and Harry are all well-documented; her off-duty looks – which were often glimpses of Diana at her most confident – are less rhapsodised about. Holidaying with her family away from the glare of the spotlight, the former kindergarten aide’s character came alive in bold, splashy prints, and colour combinations deserving of tropical shores.
“Fashion might not have been a priority, but she loved to experiment,” her stylist Anna Harvey famously told British Vogue of the royal’s penchant for pattern and a head-turning palette. Nowhere did this sentiment ring more true than in the animal-print swimsuit and sarong sets, oversized gift-store T-shirts and logo caps she packed for far-flung destinations. From Mallorca and St Tropez to the exclusive Necker Island, the glimpses of a tanned and happy Diana that emerged bore no resemblance to the Sloane Ranger style that was her default London mode.
For Corrin, Di’s downtime looks played an important role in “humanising” the royal. The princess’s personal clothes were “where she felt most natural, most like herself”, and this self-assuredness radiated out of her. It was catnip for the watching world, who took style notes from the woman who always went her own way. Her chic cycling shorts and fabulous sunglasses, amongst her other summer essentials, were precursors to myriad fashion trends – then and now.
Here, the wardrobe binders the Princess of Wales used to bring panache to her most carefree ensembles (wind-whipped ’80s hair optional).
Truly fantastic swimwear
Princess Diana’s beachwear sets are legendary. Never underestimate the power of matching coords when sailing into a port.
Lo-fi sportswear
It-girls today reference Di’s gym gear for good reason: it’s unstudied (the hardest fashion to copy). We’d take the cycling shorts and collegiate sports sweaters the royal wore in the summer over the current trend for leggings and crop tops any day.
Oversized Tees
A stack of XL T-shirts balanced out the zany sarongs in her suitcase. Throw on over a swimsuit, add a cap and big shades, and you’ve got the quintessential Diana-at-the-beach ensemble.
The go-anywhere summer dress
Prairie-style, monster-collared dresses – a Diana signature – still deserved a spot in her downtime catalogue. Useful for navigating British summertime events, feminine frocks showed the sweetest side to the princess.
High-waisted trousers and shirts
Diana excelled at the trouser tuck: tops cinched neatly into unfailingly flattering high-waisted jeans and chinos. On holiday, Diana’s signature Sloaney shirts were swapped out in favour of tank tops that showed a freer side to her style (particularly in the mid ’90s when her divorce was finalised).
Killer sunglasses
Holiday Di is a reminder of the transformative power of a great pair of shades. The bolder, the better for the late princess.
A smattering of chunky gold jewellery
Does anything look better against freckled, sun-kissed skin? A handful of gold earrings is a packing essential to employ as an instant outfit elevator, à la Diana.
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