Decades after her passing, Princess Diana’s sense of style lives on. Here are some of our favorite casual looks of hers, and how to recreate them.
It’s been 25 years since Princess Diana’s tragic passing, and the world still feels the hole she left. One of the most beloved public figures of all time, the princess was known for being silly, casual, and relatable, all of which shone through in her wardrobe. Not that her fashion sense was her most admirable trait — we couldn’t begin to explain why she was nicknamed “The Peoples’ Princess.” And we can’t really help you be as good as she was, but we can help you look the part.
While her style can never be duplicated, it’s often imitated, and it’s no wonder: Even with her incredibly slender, tall frame (she stood a statuesque 5’10), she often wore styles that were simple and accessible, that any woman would look and feel beautiful in.
One way we continue to celebrate Diana’s legacy is by looking back at Princess Diana‘s most beloved outfits and fashion moments. Given how many jaw-droppingly gorgeous looks she served over the course of her short life, it was tough to choose just eight of them to share with you. We decided that since we aren’t going to any royal engagements or international balls anytime soon (at least, most of us aren’t) we would focus on Diana’s more casual looks. Most of them are quite easy to emulate if you know where to look, and a lot of the silhouettes we’ve chosen to focus on that may have seemed just slightly dated ten years ago are back at the height of popularity. From her tongue-in-cheek “black sheep” sweater to the Fair Isle jumper and rain boots she was photographed in shortly after her engagement to Prince Charles was announced, we’ve curated some pieces that will help you emulate some of her most admired outfits. As to her perfectly feathered blonde hair, unfortunately, you’re on your own. We hope that Lady Diana would be flattered to know that she’s still our fashion north star after all these years.
The 8 Best Princess Diana Fashion Moments and How to Recreate Them
Princess Diana’s Black Sheep Look
Of Diana Spencer’s thousands of iconic outfits, this black sheep sweater might just take the cake. It so perfectly encapsulates what she must have been feeling at the time without her having to say a word.
The Sweater
Rowing Blazers
Rowing Blazers is still making the original black sheep sweater, one of which is available in “Diana red.”
The Pants
Madewell
A straight leg jean would also work for this outfit, but we’re partial to the front pockets on these workwear-inspired pants that nearly match the pair Diana wore.
The Shoes
DSW
The asymmetrical buckle on these adorable red flats mimics the bow Diana wears around her neck for a new take on the look.
The Glasses
Ray-Ban
The giant, ‘80s sunglasses are an integral part of this fantastic outfit. If your sunnies need a little boost, these Ray-Ban ones are spot on and come in prescription.
Princess Diana’s Fableisure Look
Has anyone ever in the history of the world pulled off a more memorable athleisure look? The sweatshirt! The socks! The neon bike shorts! It’s enough to make someone fall off their treadmill.
The Shorts
Alo Yoga
These bike shorts are beautiful, bright, and will make your bum look the best!
The Sweatshirt (Option 1)
Walmart
No it’s not the exact “Fly Virgin” sweatshirt, but the Chevy logo and red script have the same vintage feel.
The Sweatshirt (Option 2)
Walmart
If you’re more into the logo-less look, we found a great, super cozy solid blue one. We suggest you get it oversized. We linked here to a large, but it’s available in all sizes.
The Sneakers
Nike
To emulate Diana’s iconic high-tops, go for something with a slightly modern twist. This Nike pair is inspired by the brand’s older designs, but a sleek leather body makes it feel more modern.
The Socks
The perfect crew sock? Don’t mind if we do. Put these on and then give ‘em a nice casual scrunch.
Princess Diana’s Jumper and Wellies Look
This was one of the first outfits Diana was photographed in when she was thrust onto the world’s stage. This photo was taken just two months before the royal wedding. Diana was only 19, but she already had such a strong sense of style.
The Sweater
Farm Rio
While nothing can compete with Diana’s llamas, this cozy and colorful sweater comes pretty close.
The Pants
Everlane
These high-rise corduroy pants are about as close to Diana’s as you’ll ever find.
The Boots
Zappos
Since Diana wore them back in the ‘80s, these tall hunter green rain boots have never gone out of style.
The Socks
Walmart
You need the tall red socks for this one. We love this set as they’re light enough to wear in the summer, but thick enough for rain boots in the winter.
Princess Diana’s Blazer with a Dad Hat Look
It’s amazing to see Diana in an outfit that could easily be worn by a celebrity mom today. This effortlessly cool look is one we can’t get enough of.
The Blazer
Madewell
A breasted blazer is perfect for every season, and will make anything you pair it with look expensive. To fit a sweatshirt under it like Di or to just be on the oversized-blazer trend, opt for a size up.
The Sweatshirt (Option 1)
British Lung Foundation
For the small price of £29.99 and a pretty reasonable international shipping fee, Diana’s British Lung Foundation sweatshirt can be yours!
The Sweatshirt (Option 2)
Walmart
While Diana’s sweatshirt is amazing, this one from Champion will give you that same nostalgic feel.
The Hat
REI
On the baseball hat front, we suggest keeping it simple and letting that effortless flat brim do the talking.
The Jeans
Everlane
A la Diana, we want you to have a pair of jeans that really lets you stick your hands in your pockets. These straight leg jeans have plenty of room for that, and the medium blue wash is very similar to Diana’s look.
The Boots
DSW
Knee-high brown leather boots will give you a little bit of lift while also saying, “I might go horseback riding with the queen later.”
Princess Diana’s Pretty In Pink Look
While she’s a vision in any color, this pink palette is absolutely dreamy. Add that to the fact that fuchsia is one of the hottest colors of the season, and you’ve got more than enough reasons to borrow this look.
The Pants
Amazon
These pants are practically identical to Princess Diana’s, AND they’re high-waisted! They’re really speaking our language!
The Shoes
Amazon
A white Sperry boat shoe is a great foundational item to have in your closet, whether you’re trying to look casually regal or not. But they are a must if you’re trying to recreate this Diana look.
Princess Diana’s Preppy and Plaid Look
If there’s one thing that’s undeniable about Diana Spencer, it’s that the woman looks incredible in prints. Since we’re just featuring one monumental cold-weather item here, we’ve decided to go crazy and give you three similar styles to choose from.
The Coat
Amazon
We think Di would appreciate the laidback look of this one. Pair it with a white turtleneck or white scarf and you’ve got the look.
Princess Diana’s I’m Over-All of It Look
Are we being a little too cheeky? We can’t help it. Anyway, we’re particularly drawn to this outfit because it captures Diana as the effortlessly beautiful, fun, youthful mother that she was. Not a stuffy or starched item in sight.
The Overalls
Everlane
Are you as thrilled as we are that these are still in style?! This pair is the spittin’ image of Diana’s.
The Shirt
Everlane
This structured top has a classic pattern with a cropped twist. It’s long enough to wear with high-waisted pants and won’t be too short under overalls, either. It’ll also look nice with a blazer if you want some extra coverage.
Princess Diana’s Skirt n’ Stripes Look
Three years into her marriage to Prince Charles, Princess Diana was undoubtedly under an enormous amount of stress, yet she was so often seen with a smile on her face. This outfit brings out that cheerful, optimistic side she always showed the world.
The Sweater
Alex Mill
A classic nautical piece, this sweater will live in your wardrobe for ages. It’s not exactly Diana’s design, but the pattern and shape hearken back to the original.
The Skirt
Bloomingdales
We are overwhelmed with the chicness that this skirt is serving. Someone catch us as we swoon.
The Shoes
Everlane
These cute little pumps mean business. They’ve got that vintage feel, that feminine silhouette, and a low heel. They’re current but not in all the right ways.
