Today, my dear readers, we’ll be taking a look at some of my favourite fashion moments from the life of Diana, Princess of Wales.
In recent years, examining what women wear has been seen as a problem–specifically because men’s fashions aren’t scrutinised as closely. Let me just say, if men’s fashions were marginally more interesting, I guarantee that they’d be treated the same. Have you tried shopping in the men’s section? It’s often limited to shorts, jeans, and various t-shirts with logos on them… possibly a “formal” shirt now and again–and I use that term very loosely.
Nevertheless, I’m working on a similar list for Prince William and King Charles (if only to see if it’s possible), but goodness, is it more difficult than this one was! I instantly knew which of Diana’s fashion moments would make the list–I even knew which one would be first (yes, of course, it was that one).

1. Revenge Dress
Possibly her most famous look, Diana’s black off-shoulder gown by Christina Stambolian made headlines. Famously dubbed the “Revenge Dress” by the press (because she wore it after a certain someone went on television and confessed to adultery), Diana arrived at the Serpentine Gallery in London looking hors de prix. It was a power move like no other; that’s why this one is number one.
2. Black Sheep Jumper
A close second to the Revenge Dress, I’ve been dying to get my hands on a replica! The black sheep jumper (designed by Muir and Osborne for their Warm & Wonderful knitwear label) has become an iconic piece of Diana’s fashion legacy. She first wore it a month before her wedding, unknowingly predicting her status as an outlier in the royal family.


3. Taj Mahal Ensemble
People are familiar with the photo, of course. Who wouldn’t be? For a spouse to be photographed alone before a building that’s supposed to symbolise love? That’s a tragedy right there–but one that Diana wore very well.
Whether it was a choice or not, the striking colours of the collarless blazer, purple skirt, and matching pumps (very 90s, mind you) separated her from the background. They emphasised the solitude the media suspected she felt in her marriage. It’s a moment that’s still referenced many years later–and it’s one of my favourite looks because it feels so… problèmes de champagne.
4. Wedding Dress
It’d be criminal not to include the wedding dress on this list. The dress, designed by David and Elizabeth Emanuel, was a work of art. Hand-decorated with mother-of-pearl sequins and about 10,000 pearls, with its puff sleeves, ruffled neckline, and ball gown silhouette, it really played into the whole “fairytale” story that was making its rounds in the press.
My favourite feature of the dress–and probably the most memorable one–is the famous train that just trailed and trailed and trailed out of the carriage at St Paul’s.


5. Engagement Suit
It was difficult to pick the fifth fashion moment. I wanted it to be iconic but historically relevant. While there were so many stunning pieces to choose from (the sleeping beauty dress? The pink polka?) none of them really screamed “a moment that’ll go down in history” so much as the blue Cojana engagement suit.
It’s well known that Diana went to Harrods the day before to pick it out with her mother. It was one of her first forays into the fashion sphere–and one that would take the world by storm and set her on the journey to become the fashion icon we know and love today.
Looking back on the life of the Princess of Wales, it’s interesting to see how her style choices developed. From where she bought her blue engagement suit off the rack to her couture “Revenge Dress”, the years separating these two iconic Diana fashion moments are legendary in terms of style.
Of course, there are quite a few more Diana fashion moments that I’d like to mention. (This post got me thinking about My Top 5 Princess Diana Jumpers). These are, however, my favourite of her most iconic looks.
As I’ve said before, I’ll be working on a list for Prince William and King Charles–let’s hope that their top fashion moments don’t consist entirely of suits.


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