Princess Diana’s 30 best outfits
From the iconic cycling shorts and jumper outfits, to the revenge dress, Princess Diana’s outfits never disappointed. In fact, her taste in fashion was so ahead of her time that she continues to hold her status as a style icon to this very day.
Before her wedding to Prince Charles, Diana confessed that her wardrobe was only made up of “one long dress, one silk shirt, one smart pair of shoes, and that was it”. Yet over the years, she built up quite a collection of striking and memorable looks.
We’re going to take a deep dive into the look book of Princess Di, looking back on 30 of the best outfits she ever wore.
Ready for the ultimate style inspiration from Lady Diana herself? Let’s do it.
Teacher chic
In 1980, Lady Diana was snapped at the Nursery School she was teaching at, wearing a midi skirt paired with a long sleeved blouse and sweater-vest. We would absolutely still wear this today.
Wedding guest dress
Attending the wedding of Nicholas Soames and Catherine Weatherall, Lady Diana turned heads in a red polka dot, high neck and long sleeved dress.
Preppy
In 1981, Lady Di attended a polo match wearing a Liberty print shirt, matched to some yellow dungarees and pink espadrilles.
Princess Diana’s Wedding Dress
At her own fairytale wedding, Princess Diana wore an ivory silk taffeta bridal gown by Elizabeth and David Emanuel. The train of the dress was 25 ft long, the longest ever royal wedding dress! It had 10,000 pearls and stunning details. She wore her family heirloom the Spencer tiara which had been in her family for decades.
The neutral trench coat
On the newly weds’ first official visit to Wales, Diana wore a beige Caroline Charles coat with a feather-detail John Boyd hat.
Babydoll core
Okay, okay. This dress may not be to everyone’s taste. But the fact that Princess Diana could pull it off so magnificently speaks volumes. She wore this princess dress to the “Splendours of the Gonzaga” exhibition at the Victoria and Albert Museum in London.
Pretty in Blue
Looking stunning as always, Princess Diana attended a charity concert in a spotted blue dress by her wedding dress designers.
Ballet Core
In December, we wear red, glittering dresses. Princess Di attended a ballet at the Royal Opera House in Covent Garden.
Flowing dresses
Though technically a Princess, Diana was certainly the Queen of Modest fashion. Here she is at a school in Australia in a long yellow dress with white pumps and a gold bracelet.
Glitz and glam
Princess Diana opted for full glamour to attend an event in Melbourne, wearing a white Bruce Oldfield gown.
The Harry Styles Jumper
The jumper that influenced Harry Styles. Diana wore her Muir and Osborne “black sheep” sweater with white jeans to attend the polo.
The Matching Set
A look that we’d all wear today — Princess Diana went to the Polo with her friend in a matching skirt and blouse two piece.
Virgil’s Off-White Inspiration
Diana wore all her best looks to the Polo. Her outfit here in 1983 served as the inspiration for Virgil Abloh’s spring/summer 2018 Off-White collection.
A Monochrome Moment
The royal fashionista wore this monochromatic dress to an event in Saudi Arabia, 1986.
A Starry Sensation
What better outfit for the he Phantom of the Opera than a navy blue Murray Arbeid dress and hot-pink opera gloves?
Cannes Film Festival Dress
Diana serves as inspiration for anyone attending the Cannes Film Festival, wearing a strapless baby-blue Catherine Walker dress.
The Lemon Suit
Even in a suit, she manages to bring that classic soft Diana touch.
The School Run Outfit
While we’d like to think that this outfit was carefully thought out and put together, the smirk on Princess Di’s face kind of says otherwise. After all, it is the school run.
In all fairness, we can see ourselves wearing baggy trousers, cow boy boots, a blazer and a cap in this day and age.
The Striped Rainbow Dress
We cannot get enough of this striped dress. It’s everything. And it looks great with the velvet blazer. Obsessed.
The Sports Day Look
The camel skirt is giving, but her running is giving even more. Reason 1639257726 why we love Princess Diana.
The Black Bomber
There’s just something about Princess Di in a black bomber that is so hot. Gen-Z would be proud of her for picking slim jeans over skinny!
The Revenge Dress
Diana wore this black minidress by Greek designer, Christina Stambolian on the same evening that a documentary aired in which Prince Charles admitted to being unfaithful during their marriage. It thus became known as the “Revenge Dress” and boy does she look good.
The Casual Blazer
Diana headed out shopping in Knightsbridge in a neutral grey blazer, with a white turtleneck and trousers.
How does one look so good in such a simple outfit? It’s the Diana effect.
Little White Dress
Diana wore a short white Versace dress to attend the Children of Bosnia charity concert in Modena, Italy. She was well and truly in her villain era here.
Cycling Shorts and Jumper Outfit
It’s the moment we’ve all been waiting for — Princess Diana in the cycling shorts and jumper outfit.
The Lace Slip Dress
Diana attended the Met Gala in New York, 1996 wearing a beautiful John Galliano for Dior slip-style gown with her sapphire choker.
The Full Length Gown
Diana wore this navy dress by Catherine Walker to the premiere of In Love And War with director Richard Attenborough.
The Chanel Suit
Diana wore her pale blue Chanel suit on several occasions. Here, she visiting the British Lung Foundation in Hatton Garden, London.
The Floral Mini Dress
Princess Di attended a cocktail reception in an embellished floral cocktail dress along with her Jimmy Choos.
The Bikini
On her holiday to the South of France, Diana wore this pretty painterly bikini.
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