Princess Diana—Her Best Outfits and Style Influence Today

Hiiii guys and welcome back to another day of Haute Take!! Today we are discussing a super fun topic that I personally LOVE talking about—Princess Diana’s fashion.  

Known as the “people’s princess”, Princess Diana’s style was one that was way ahead of its time. Over her years in the spotlight, she wore several incredibly memorable outfits that still influence people’s style all over the world today. From her “off-duty” workout outfits to her iconic “revenge dress”, Diana never failed to look put together and elegant no matter what she was doing. While she often followed royal dress codes, she also pushed boundaries, proving that style is about self-expression. Whether it was her love for structured blazers, her sporty ‘90s aesthetic, or iconic dresses, Diana’s ability to make a statement through fashion was unmatched. Let’s take a closer look at her most memorable outfits and how her legacy continues to shape the way we dress today! 

My Top 5 Best Princess Diana Outfits

Princess Diana never failed to serve iconic, effortless elegance. While some of her outfits may have been a miss for me, she still had so many incredible looks that deserve all the praise. While it was so hard to pick a top 5, and even harder to put those top 5 in order, here are my favorite looks of hers!

First lets take a brief moment to acknowledge her ICONICCCCC absolutely GORGEOUS street style, since I only really included her outfits that were worn to specific events in the top 5. So here are three honorable mentions (in no particular order), before we get started.

All black business outfit? yes.

Off-duty athletic outfit? yes.

Put together casual streetwear? yes.

Alright! So now that those are out of the way, in fifth place, we have this gorgeous all PINK outfit (obviously I had to include) designed by Catherine Walker. She wore this while arriving in Sicily in April 1985, and it could not have been more perfect. The puff sleeves, the color, the pearls, everything about it is just gorgeous. And we all know how much I love my light pink 🥰The only thing I would change is having a silver watch instead of gold, but that is just me being picky. Overall, she killed this look! 

In fourth place, we have her iconic revenge dress. She wore this gorgeous black off the shoulder dress by Christina Stambolian while arriving at the Serpentine Gallery in London. This dress was later deemed to be her “revenge dress” following the public announcement of her husband Charles affair with another woman. All I have to say is ICONIC. She always loved to rock her off the shoulder tops and dresses, and this one just takes it to a whole new level. Everything about this outfit just screams single lady, ready to take on the world. It goes against the typical modest, prim and proper outfits, and was honestly the turning point of her style in which she began to expand her looks and push the boundaries of your classic royal family wardrobe. And for the 100th time...ICONIC.

In third place, we have this stunning white fitted suit dress by Catherine Walker. This dress is just giving elegant, old money aesthetic and it is just everything. From the color, to the fit, it is just perfectly suited for her and her style. She also usually loved to wear very vibrant colors, which is not really much my style, so seeing her in these more muted neutral tones is everything. The only thing I would change though? The hat. But other than that, an absolutely stunning outfit. 

In second place, we have one of her many iconic streetwear outfits, which provide such inspiration for how I want to dress when I am grown and a mom dropping off my kids at school. It just screams put together yet effortless at the same time. She also ALWAYS made sure the little details of her outfits matched, as seen by the shoes, bag, belt and sunglasses in this photo. My personal fashion sense is all about aesthetics and making sure the outfit is appealing to the eye as well as all cohesive and matching, so I appreciate when others also share that same interest. AMAZING.  

And finally, in number one, we have this absolutely GORGEOUS ✨pink✨ and white outfit she wore to a Swan Lake performance in London. I. Love. This. Outfit. Literally everything about it is simply perfection, you cannot tell me otherwise. To start off, just LOOK at that COLOR?? The pink is just so beautiful and matches her skin tone and color palette so incredibly well. And I always love a good pink and white moment. Also, going back to what I said before on the matching, cohesive outfits, every single item in this outfit matches. The way the skirt, purse, and SHOES (the shoes are a statement in themselves, I need them immediately) all match perfectly, the way the white and pink blend so well together, and the way the pearl earrings flawlessly match the white? Absolutely stunning. AND the slit in the back of the skirt adds the most gorgeous flow to the outfit, making it look comfortable and wearable while still being so proper and put together in the best way. Anyways, no complaints, no critiques. Slayed.

Diana’s Lasting Style Influence 

Even today, Diana’s influence is everywhere. Her signature oversized sweatshirts and biker shorts? A go-to off-duty look for influencers and models or even workout outfits. Her love for tailored blazers? A staple in business outfits and those attempting to follow the classic “old money” aesthetic. Her elegant evening gowns? The blueprint for modern red-carpet glamour. 

Fashion is all about reinvention, and Diana’s timeless aesthetic continues to evolve with each new generation. Whether it’s through archival-inspired runway collections, vintage revivals, or modern adaptations of her most famous outfits, her legacy remains just as powerful as ever. 

Are you as obsessed with Diana’s style as I am? Let me know which of her looks is your all-time favorite in the comments! Thanks for reading today’s blog!! See you next time 😊 

xoxo, 

Leah <3