5 Princess Diana Outfits That Will Make You Want to Live in Jeans and Blazers

Princess Diana's style has remained one of the biggest influences in the fashion world over the past 30 years with a number of her outfits proving as iconic now as they were when she first wore them. Whether you realise it or not, so much of what we wear today is inspired by the royal’s fashion choices, from her cycling short gym looks to her effortless white shirts—all still visible on the catwalks of the last few years. Trust us, a quick Google search or scroll through the many Diana tribute Instagram accounts (we advise you follow them all) will provide all the new-season inspiration you need.
Our favourite Diana looks, though, all have one thing in common: denim. These days you don't often (or ever) see Kate, Meghan or *whispers* Camilla wearing blue jeans— but somehow Diana always managed to pull them off while still looking royal as ever. In particular, she was a big fan of the jeans-and-blazer combo, which we think might have been her secret.
The epitome of high-low dressing, the iconic jeans-and-blazer outfit remains to this day a fashion-girl staple— likely because it makes an inherently casual wardrobe basic instantly feel pulled-together. As Diana proved, it's appropriate for so many occasions. From shopping trips to airport attire, sporting events and even speech-giving. In fact, after doing some digging into the Diana archives, we're pretty sure she's the reason our jeans-and-blazer obsession even exists in the first place...
Keep scrolling to shop some of her most recognisable combos (and ogle at how ahead of the times she was with her looks).
Style Notes: Without this blazer, Diana's sweatshirt and jeans outift would come across as super casual. The oversized silhouette which has inspired the likes of Balenciaga is the ultimate in power jacket.
Style Notes: Diana confirms the outfit-enhancing, appropriate-for-anything qualities of the blazer here. Let's also note the classic Supergas which we've just added to our capsule wardrobe shopping list.
Style Notes: So many trends in one outfit: tonal dressing, checked blazer, tights under jeans and chic ballet flats. We bow down.
Style Notes: Diana knew the timeless elegance of a crisp shirt. Just add black jeans, a buttoned blazer and gold earrings for a look that transcends time and trends.
Style Notes: The sunglasses, the gold hoops, the Western belt, the white jeans—this outfit couldn't be more now if it tried.
Up next: The Trending 2021 Items That Princess Diana Wore First

Emily Dawes is an editor, stylist and writer with over 12 years in the industry. Known for impeccable taste, our readers trust her advice, especially in her top-selling column, expensive-looking high street buys. Working for Who What Wear UK since 2020, Emily has been a contributing editor, branded content editor and affiliate editor. Now, as senior shopping editor, she leads the e-commerce content strategy. After obtaining a BA in English and American Studies from Nottingham University, Emily interned at The Mail on Sunday’s YOU. As the magazine’s fashion editor, she managed the fashion team and travelled the globe to style and direct fashion editorials and celebrity cover shoots. As a freelancer, she styled Grazia cover shoots, developed brand marketing and content plans and worked with VIP clients including Elizabeth Day.
-
FYI: This Shirt Trend Makes Jeans Look So Much Prettier
Yes, pretty.
-
The New Rules of Summer Denim: No Rips, No Fray, No Fuss
See the full set of rules inside.
-
The Anti–Skinny Pants Trend Cool New Yorkers Are Quick to Ditch Their Blue Jeans For
Buh-bye.
-
Every Cool New Yorker Knows These Anti-Trend Flats Look Better With Jeans Than Boots and Sneakers
Classic and chic.
-
I Called the Cuffed-Jeans Trend—7 Shoes Fashion People Are Wearing With the Chic Denim Style
Style the jeans like a fashion person.
-
Stop the Search—We've Discovered the Cool Denim Trend Every Fashion Person Will Be Wearing Throughout 2025
And 2026.
-
If The Row, Khaite, and Toteme Feel Too Expensive, Here Are 33 Pieces to Try Instead
Bring on the luxe-looking outfits.
-
9 Top, Jeans, and Shoe Outfit Combos That Fashion People Will Be Wearing This Spring
I plan to re-create these ASAP.