10 iconic Princess Diana street style moments
These are the looks that we still adore today...
Princess Diana's inimitable (much as we may try) approach to street style will go down in fashion history. She won the people's hearts with her grace and sensibility, but her trailblazing tendencies extended beyond humanitarianism – just ask Gen Z.
TikTok audiences are utterly obsessed with her off-duty looks, so much so that the hashtag #princessdianastreetstyle has amassed a whopping 57.4m views on the platform.
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Remarkable in itself, but in the context of fashion's ever-changing nature, the fact that so many of us are lusting after three-decade-old outfits is positively mind-blowing. (Although perhaps not after you reacquaint yourself with some of the princess' strongest looks.)
When Princess Diana first entered the public eye, her outfits were extremely of their time. Think twee cardigans, Edwardian-esque frills and a plethora of pussy bows – all extremely 80s, and yet, these prim pieces possessed a certain girlish charm and captured her ingénue spirit.
Over the years, she gravitated towards pieces with a slightly cooler edge. Arguably pioneering the now-omnipresent athleisure trend, Princess Diana's gym uniform (baggy graphic sweatshirts, cycling shorts, tube socks and chunky sneakers) is still utterly relevant today.
She turned royal fashion on its head with her chic school drop-off looks (think baseball jackets and utility-style midis), cementing her status as an outfit icon. Suffice it to say, whittling it down to just 10 was nothing short of agonising.
Hello! Fashion shares Princess Diana's most iconic street style moments:
Polo Chic, 1987
Not technically on the street, but Princess Diana's look worn on the grass at the Guards Polo Club is too good to miss.
Tennis Chic, 1988
Princess Diana remained stylish on every single occasion.
Guards Polo Club, 1988
The princess' balloon sweatshirt has since become one of her most iconic pieces.
The School Run, 1989
The stylish royal wore a belted pale pink utility-style midi dress to pick up Prince Harry after nursery.
Devon, 1990
Princess Diana looked resplendent in a tartan coat-dress by Catherine Walker during a visit to Devon.
Out in Knightsbridge, 1994
Princess Diana layered a blazer over a cream polo neck for a trip to Knightsbridge. She paired the look with two-tone loafers and oversized sunglasses.
The sweatshirt and shorts, 1995
In 1995, Di styled a navy Virgin Atlantic sweatshirt alongside orange cycling shorts.
Skiing in Austria, 1994
The princess donned a vibrant puffer jacket while on a skiing holiday in Austria.
Chicago, 1996
She stunned in a cream shift dress, a pearl necklace and a beige shoulder bag for a trip to Chicago.
The School Run, 1997
Princess Diana's Philadelphia Eagles jacket was one of her most treasured pieces of outerwear. She nailed high-low dressing by pairing it with a mini skirt.
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