Dressing like Diana has become somewhat of a national pastime these days, especially among Gen Z. But as a royal editor—and someone who is actually old enough to remember what it was like when Princess Diana died—I have a different perspective on her fashion legacy. I also happen to have a fairly photographic memory when it comes to her casual outfits, which comes in handy in my line of work.
There's something about Princess Diana's style that transcends decades and trends. "Fashion is of course cyclical, and Diana’s style archive is this treasure chest that designers keep going back to," Eloise Moran, author of The Lady Di Look Book and creator of the Instagram account Lady Di Revenge Looks, tells Marie Claire.
"She’s someone I’ve always described as the ‘every woman'—she had that rare quality where she could feel both aspirational and totally relatable," Moran adds. "Like Carolyn Bessette, she dressed herself, and there was just this inherent creativity and timelessness to the way she put herself together."
Moran notes that Princess Diana's style also "evolved so much" over the years, giving her the opportunity to try everything from "fairy tale" looks to "androgyny" and '80s glam. Perhaps that's why so many of the late princess's pieces still feel so fresh today—eventually, all of these looks are bound to come back in style.
Although I own numerous royally approved bags and pieces of jewelry that Kate Middleton and Meghan Markle have worn, I'm much more likely to wear outfits like Diana's—which sparked the idea for this story. Why not wear Princess Diana-inspired outfits for an entire week? The concept was easy enough, but what I didn't expect was how much these outfits changed my mood and even boosted my confidence.
I walked a little taller and felt more pulled-together, but I noticed the Diana effect even more when I stopped the experiment—so much so that I'm back to wearing a black Di-inspired dress while I'm writing this story.
Sloane Ranger
One of my all-time favorite Diana outfits is one she wore ahead of her engagement to Prince Charles. It's a a classic Sloane Ranger aesthetic: Fuzzy white cardigan, blue button-up shirt, pants, pearl necklace and a scarf. I was on a mission to recreate it for years, but could never find the perfect cardigan until I came across this Boden style a few years ago. Luckily, jaunty silk scarves are all the rage this season, and I thought there was no better time to kick off this fashion challenge than the day I went to visit some of Diana's most famous fashion pieces.
Luckily, it happened to be an unseasonably cold and rainy day in NYC so I was able to wear a heavy sweater to the press preview for Julien's Auctions's "Princess Diana's Style & A Royal Collection" event. And what better opportunity to wear my beloved Union Jack Hunter wellies? (Sadly, these are more than a decade old and no longer available, but I've linked similar below.)
While the auction itself isn't until June 26 in Beverly Hills, I got to see Princess Diana's floral "Caring Dress" that she wore on numerous trips to visit children's hospitals and a few other iconic looks—and even held her black Lady Dior bag, something I never imagined actually doing.
Virgin Atlantic Sweatshirt
There's no way you can dress like Diana without recreating one of her most iconic outfits: bike shorts with a crewneck sweatshirt. The princess wore numerous variations of this look, including Harvard, Northwestern and USA-themed sweatshirts when she went to her gym, the Chelsea Harbour Club.
I've had this replica of Diana's Virgin Atlantic design for years, and although it was way too chilly to be wearing shorts at the beach on this particular day, I toughed it out for the project. Etsy is a fantastic source if you're looking for an exact copy of Di's Virgin Atlantic shirt, but the great thing about this combo is you can really pair any sweatshirt with bike shorts and get that royal feeling. For a bit of a Chelsea shout-out, I added my own beloved Chelsea FC cap. Even if Diana didn't publicly support a football team, I have a feeling she'd be one of The Blues.
Crisp White Shirt and Jeans
Diana wore this look during a trip to Bosnia in August 1997, just weeks before her death, but she also wore other variations on the tucked-in button-up shirt and jeans over the years. I wore this on a Saturday and felt just a tad overdressed at my son's game amid a sea of sweatpant-wearing parents...but also way more pulled-together.
This is admittedly not something I'd ever have worn without Diana's inspo, as simple of an outfit formula as it is. I'm more likely to be seen in a floral print or bright color than a classic white shirt, but combined with gold jewelry and my Gladstn London tote, it gave off quiet luxury vibes and definitely boosted my mood.
What I love about this elevated casual option is that doesn't look out of place running errands, but makes you feel just that extra bit more polished. It's also giving '90s mom, as my son confirmed when he declared that I "looked just like Mary Cooper on Young Sheldon in that episode where the dad dies." Mission accomplished?
Prairie Collar Shirt
While this isn't an exact recreation of a Diana look, she never met a wide collar she didn't like. From dresses to blouses, she often wore styles with prairie collars accented with ruffles, frills and embroidery.
The options are endless when it comes to this style, but my new Anthropologie blouse is one piece that can go with everything from jeans to shorts to skirts—I'll be getting plenty of use out of it this summer. A collar like this makes any top feel more special than a T-shirt, but it's just as cute on a dress (my favorites are from Reformation and Kate-approved designer Alessandra Rich).
Flowy Pink Dress
I'm definitely not pregnant, but I've always loved this pink maternity look Diana wore to a polo match while she was expecting Prince William. To my surprise, I found the perfect dress while picking some things up at a Kohl's near my in-laws over Memorial Day weekend. Bubblegum pink isn't my color, but this jewel-toned shade works if you've got a similar skin tone.
I went up one size for a more relaxed fit, and this was the ideal dress for a Friday of running errands (this particular shot was taken in an H&M fitting room after returning some fails from my Diana fashion quest). I accessorized with two Princess Kate pieces: Her Spells of Love Alia hoops and a gold bangle from Jamaican brand Steelz and Mantraz that the princess wore on her 2022 Caribbean tour.
Button-Front Skirt
Sadly, I'm skipping out on the butter yellow trend this year, but Diana happened to be the OG yellow influencer. While I tried (and returned) a similar blouse to the one Diana wore in the above photo, pairing a chambray shirt from my closet with a button-front skirt proved to be a much better option.
Diana loved a big button earring, although Chanel could be a risky gift, as her former butler, Paul Burrell, told me last Christmas. I think she would've enjoyed these Lavished Renewed earrings, despite the double C association (Charles and Camilla...). The company upcycles designer buttons and zipper-pulls into jewelry, so no two pieces are the same.
White Dotted Dress
When I think of Royal Ascot, Diana's white dress with black polka dots immediately comes to mind. It's a look the Princess of Wales recreated years later when she wore a very similar Alessandra Rich dress—and when it comes to my own Ascot outfit this year, I'm leaning towards the dotted aesthetic, too (more to come there).
For my niece's recent graduation, I pulled a River Island dress out of my closet that I hadn't worn since Queen Elizabeth's Platinum Jubilee. This time, I replaced the included belt with a red bow-trimmed style—a trick Diana often used to give a pop of color to an outfit.
