diana© Photo: Getty Images

Princess Diana's top 10 most iconic fashion moments ever

The People's Princess had the best wardrobe around…

Fashion and Beauty News Editor
August 31, 2022

It's safe to say that Princess Diana was one of the most famous fashion icons of all time. She was so ahead of the curve with her wardrobe, donning an eclectic array of styles - cycling shorts, oversized sweaters, pie crust necklines and striking heels to name a few. 

READ: 14 of Princess Diana's cutest mum moments with William and Harry

She also rocked a variety of designer labels that are still very much on point today - not to mention the most desirable couture names in British history. 

With Wednesday marking 25 years since her passing, we have put together her most iconic outfits from some of her go-to designers. Which one is your favourite?

WATCH: Princess Diana's Enduring Fashion Legacy

The little black dress

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Diana dazzled in this Christina Stambolian dress

In at number one, we have the infamous little black dress by Christina Stambolian. The press nicknamed the frock the 'revenge dress' as Diana wore to a soiree on the day her husband admitted to infidelity in a televised interview. Accessorising the daring hem with heels, opaque tights and her trademark choker, this dress will be remembered forever.

Wedding Dress

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The wedding dress no-one could forget

Undoubtedly the most famous wedding dress of all time is Princess Diana's bridal gown. The fairytale style is instantly recognisable due to the huge skirt and statement puff sleeves. Designed by David Emanuel, it is truly iconic; especially as it featured a record-breaking 25-foot train and 10,000 mother of pearl sequins and pearl embellishments. Wow.

READ: Princess Diana's most iconic wedding guest outfits to recreate in 2021

The pastel mini dress

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Princess Diana stole the show in this pastel mini frock

The Princess of Wales was known for her impeccable taste and was the queen of eveningwear. As an independent, single woman following her divorce, Diana loved sporting a sleek silhouette and made jaws drop in this pale blue, fitted shift for a gala performance of Swan Lake at the Royal Albert Hall, just two months before her death.

The blue one-shoulder gown

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A silk gown made by Versace

Diana was a great friend of Gianni Versace and he made some truly wonderful frocks for the royal. The Princess always looked great in one-shouldered gowns and this electric blue creation by the designer ensured she stood out from the crowd.

READ: 8 times Meghan Markle channeled Princess Diana's iconic style

The nautical co-ord

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Princess Diana was the ultimate stylish sailor

It's hard to pull off an all-white outfit with military details, but Diana smashed it with this memorable number, even adding a sailor hat! This ensemble was created by Catherine Walker and her white headgear was designed by Graham Smith at Kangol. She rocked the getup during a visit to the Royal Military Academy Sandhurst in 1987 as she wanted to pay homage to her military hosts.

The sporty shorts

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Diana's sporty look is easily one of her most famous

Diana stepped out in her iconic peach-coloured cycling sports which she paired with an oversized graphic jumper as she left the Chelsea Harbour Club in 1995. The look has become a distinctive image of the nineties – and proved that the royal could nail a sportswear look in addition to a glittering evening ensemble.

Jeans and oversized blazer

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The royal looked incredible in denim

The People's Princess epitomised eighties style during a day out at the Guards Polo Club. She dressed casually, sporting a jumper that boasted The British Lung Foundation Logo on the front, blue jeans and an oversized blazer with some powerhouse shoulder pads.

The iridescent black dress

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Diana loved a black dress moment

Prince Harry and William's mother looked truly mesmerising in a black evening dress designed by Jacque Azagury while attending a gala evening in aid of Cancer Research at Bridgewater House in London back in 1995. She wore her statement necklace with the number – a piece of jewellery famously donned when she stepped out in her iconic 'revenge dress' a year prior in 1994.

The pink set

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The beloved princess looked pretty in pink

The royal looked pretty in candy pink during a visit to Argentina in 1995. She looked radiant in the carefully cut two-piece which featured a tailored, double-breasted jacket featuring short-sleeves and button-down detailing, and a coordinating pink skirt.

Polka dot frock

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Diana liked to play around with feminine prints 

Finally, Princess Diana channelled divine femininity in a polka dot frock during Derby Day at Epsom racecourse in Surrey in 1986. The garment, which was designed by Victor Edelstein, was elevated with a hat crafted by Frederick Fox. She completed her classic ensemble with some white tights and two-tone cream and black point-toe heels.

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