Reimagining Princess Diana’s Most Iconic Looks

This year marks the 20th anniversary of Princess Diana’s death. There has been a slew of documentaries in the UK (some good, some bad) and a refreshed homage to her legendary style. After all, the royal family’s first ever bonafide global celebrity was not just a beautiful young princess; she was, and remains to this day, the ultimate fashion icon.

Princess Diana was the quintessential Sloane Ranger. Used to describe a certain kind of boarding-school-educated British gal from the upper class or the upper middle-class (I’m not going to explain the British class system here; I don’t have 20 years to write this), the “Sloane Ranger” (a term born in 1975) is a portmanteau of Chelsea’s Sloane Square and Lone Ranger. The Sloane Ranger still exists today, in watered-down form, but her apex was the ’80s: the decade in which Princess Diana became a national and global obsession.

She favored two-tone court shoes, polkadots and pearls, stonewash jeans, baggy sweaters, pink suits in every conceivable cut and hue, tweedy jackets, puff-sleeved tartan and jaunty berets, big gold clip-on earrings, white stilettos and ruched evening dresses. She wore white jeans with white t-shirts and loafers (hi Leandra!) and pink with purple was her colorway of choice. Her favorite labels were Catherine Walker, Bellville Sassoon, Bruce Oldfield and Victor Edelstein.

But what would Princess Diana wear today? According to Kate Finnigan for The Telegraph’s Stella magazine, “Stealth chic would be her thing.” She’d favor “white J Brand jeans, cashmere round-necks” and houses such as Ralph Lauren, Ralph & Russo, Tom Ford, Valentino and Chanel.

I, on the other hand, prefer to re-imagine her aesthetic as something bolder, and cooler, in outfits that might make the same impact that she did back in the ’80s. So I took her iconic looks and updated them for 2017. It helps, of course, that so much of what Diana wore is back: the polkadots, the pearls, the tartan and tweed and frilly shirts and faded Levi’s and white stilettos and clip-on gold earrings and white-worn-with-white-and-loafers and PINK SUITS. So many pink suits. You know I love a pink suit.

I was conscious while writing this piece that I didn’t want to be exploitative or piss-takey. I wanted my looks to be playful but firmly within the boundary of “homage.” For that reason, I chose not to shoot one of my favorite outfits, worn by Diana while out on a jog: cropped cycle shorts, thick eighties athletic socks, white sneaks and an oversize gray Harvard sweater. Diana once spoke about how the paparazzi hounded her whenever she went running. Thus, I only re-interpreted looks that she wore publicly (rather than privately), when she was “on ceremony” and dolled up to the nines.

In one of my favorite portraits of Diana, she wears a tartan blazer and beret. Today, I like to imagine she’d be drawn to Balmain. Any beret-wearer worth her salt knows that Itchy Scratchy Patchy, co-helmed by supermodel Edie Campbell and her artist best friend, Christabel MacGreevy, is the way forward. The beret spells anarchy, because to the reticent and reserved royal family, Princess Diana was anarchic.

Ganni suit, vintage floral shirt -- another here, vintage earrings -- similar here, Manolo Blahnik mules Ganni suit, vintage floral shirt -- another here, vintage earrings -- similar here, Manolo Blahnik mules

Polkadots were to the 80s what Monse is to polkadots now. This cut-out, bias-cut, leg-split polkadot dress is a 2017 spin, and according to Kenneth Jay Lane, the pearl choker is back. Strangely into it. Diana was rarely without a white court and white shoes are everywhere right now, not just in my wardrobe. Gianvito Rossi even makes the exact glossy black toe-capped white court she loved, if you think you can handle it.

Last but not least, the quintessential Diana look, barely untouched by me because it’s timeless: A tweedy blazer. A frilled shirt. Faded jeans. A big brown belt. Ice-white heels. She wore it then, I’d wear it now.

Hair by Hershesons, photos by Frances Davison.

Pandora Sykes

Pandora Sykes

Pandora Sykes is a contributing editor at Man Repeller, freelance journalist, stylist and consultant of She is also the co-host of the weekly news/pop-culture podcast The High Low. Follow her on Twitter @pinsykes @thehighlowshow and Instagram @pandorasykes.

More from Archive