10 iconic Princess Diana street style moments

Orin Carlin
·2-min read

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.

princess diana baseball cap
princess diana baseball cap

READ: Princess Diana's most iconic winter outfits

MORE: Mary Greenwell shares her royal-approved beauty tips

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.

READ: Every supermodel is copying Princess Diana's favourite street style accessory right now

MORE: Nicola Peltz's latest outfit was straight out of the Princess Diana playbook

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 to say, whittling it down to just 10 was nothing short of agonising.

Hello! Fashion shares Princess Diana's most iconic street style moments:

Princess Diana, Princess of Wales styles a navy Virgin Atlantic sweatshirt alongside orange cycling shorts
Princess Diana, Princess of Wales styles a navy Virgin Atlantic sweatshirt alongside orange cycling shorts
The stylish royal wore a belted pale pink utility-style midi dress to pick up Prince Harry after nursery
The stylish royal wore a belted pale pink utility-style midi dress to pick up Prince Harry after nursery
Princess Diana's Philadelphia Eagles jacket was one of her most treasured pieces of outerwear
Princess Diana's Philadelphia Eagles jacket was one of her most treasured pieces of outerwear
The princess' balloon sweatshirt has since become one of her most iconic pieces
The princess' balloon sweatshirt has since become one of her most iconic pieces
Princess Diana layered a blazer over a cream polo neck for a trip to Knightsbridge
Princess Diana layered a blazer over a cream polo neck for a trip to Knightsbridge
The princess donned a vibrant puffer jacket while on a skiing holiday in Austria
The princess donned a vibrant puffer jacket while on a skiing holiday in Austria
Princess Diana remained stylish on every single occasion
Princess Diana remained stylish on every single occasion
Princess Diana opted for a cream shift dress, a pearl necklace and a beige shoulder bag
Princess Diana opted for a cream shift dress, a pearl necklace and a beige shoulder bag
Not technically on the street, but Princess Diana's look worn on the grass at the Guards Polo Club is too good to miss
Not technically on the street, but Princess Diana's look worn on the grass at the Guards Polo Club is too good to miss
Princess Diana looked resplendent in a tartan coat-dress by Catherine Walker during a visit to Devon
Princess Diana looked resplendent in a tartan coat-dress by Catherine Walker during a visit to Devon

Like this story? Sign up to our Hello! Fashion newsletter to get your weekly 'Fashion Fix' delivered straight to your inbox.

Latest stories