We Recreated 11 Of Princess Di’s Best Looks

Whether you're a monarchist or not, with season four of The Crown becoming the show of lockdown 2.0, there's no doubt you'll be drawn into the fanfare surrounding this season's central figure, Princess Diana (played by newcomer Emma Corrin). Tantalising court drama aside, for us the excitement lies in the show's costumes. The supersize meringue wedding gown is of course be a highlight but beyond the showstopping fashion moments that punctuated Princess Diana's royal engagements, it's her off-duty style which continues to strike a chord.

While photos of her in frou-frou Laura Ashley-esque dresses or a minimalist LBD and pearls circulate Instagram's best '80s and '90s throwback accounts, many of the pieces Diana influenced people to wear at the time have come back around – just ask Virgil Abloh and Alessandra Rich, designers who have each paid homage to the princess, or Hailey Baldwin, who broke the internet with a Miss Vogue shoot dedicated to Di's best looks.


"She was ahead of her time," Rowing Blazers founder Jack Carlson told Refinery29 ahead of the brand's launch of reissued Princess Di knitwear. "She perfected the art of mixing high and low, and blurred the lines between menswear and womenswear. She was doing streetwear before streetwear was a thing — but at the same time she was the archetype of the Sloane Ranger! She was all of these contradictions, and that’s what made her so iconic – and what makes her so relevant to what’s happening in fashion now."

Ahead, we've recreated 11 of Princess Diana's most enduring looks, from lockdown-appropriate loungewear to Ganni-esque XXL collars.

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Diana dons rain-appropriate wellies with corduroy trousers and homespun knitwear at Balmoral.
BEYOND RETRO 1980s Pink Jumper, $26.00 Buy
Toast Cord Tapered Trousers, $135.00 Buy
Hunter Original Tall Boot in Hunter Green, $95.00 $69.95 Buy
This look, which Diana wore to the gym, has been much copied and with good reason. A vintage sweatshirt, bike shorts and retro kicks is surely the perfect lockdown outfit formula.
The East End Thrift Store Vintage 90s Team Philips Blue Sweatshirt, $24.94 Buy
Girlfriend Collective High Rise Shorts in Honey, $40.00 Buy
New Balance 452 Trainers, $60.00 Buy
Princess Di was sporting XXL collars long before the likes of Ganni, Gucci and Rixo ushered in their return. Team with a floral skirt and patent belt, like Di at the polo.
Monki Sailor Collar Blouse, $30.00 Buy
Gucci GG Logo Belt, $305.00 Buy
BEYOND RETRO 1980s Floral Print Maxi Skirt, $18.00 Buy
Another 10/10 look from a polo match. If we ever get around to wearing workwear and jeans again, you'll find us teaming them with baseball caps, charity sweatshirts and cowboy boots.
Karen Millen Luxe Wool Blend Suit Jacket, $129.00 $90.30 Buy
Weekday Rowe Extra High Straight Jeans, $40.00 Buy
Isabel Marant Danta Leather Western Boots, $680.00 $272.00 Buy
We're pretty sure we saw this exact look (from yet another polo match) on Instagram this summer. Find pastel-hued dungarees, add a vintage floral blouse and some espadrilles and you've got a staycation 2020 look sorted.
Dôen Jane Floral-Print Cotton-Blend Voile Blouse, $170.00 Buy
Fila Embroidered Logo Dungarees, $91.00 Buy
Castañer Carina 60 Canvas and Jute Espadrille Wedges, $85.00 Buy
Photo: Tim Graham/Getty Images.
Princess Diana on a ski trip to Austria in the '90s or Balenciaga AW16?
Rowing Blazers Navy "All is Vanity" Unicorn Nylon Cap, $90.00 Buy
Pieces Oversized Cat Eye Sunglasses, $12.00 Buy
Weekday Hedda Puffer Jacket, $70.00 Buy
Further proof that no one wore a blazer like Princess Di, here she is shopping in Knightsbridge. Brownie points for the matching two-tone accessories.
Zara Oversized Blazer, $59.99 Buy
Isabel Marant Étoile Corsy High-Rise Jeans, $195.00 Buy
G.H. Bass & Co. Weejuns Penny Loafers Black & White Leather, $130.00 Buy
Cottagecore, eat your heart out! This ruffled polka dot dress – complete with clutch, ballet pumps and pearls – was worn by a pregnant Diana in the Scilly Isles in '82 but could easily be found on our Instagram feeds today.
Benjamin Fox Isabella Dress, $180.00 Buy
Miu Miu Vintage Black Leather Clutch Bag, $85.00 Buy
ASOS DESIGN Leather Bow Ballet Flats, $25.00 $20.00 Buy
Photo: Tim Graham/Getty Images.
If this doesn't scream "popping to the shops on our lunch break while WFH", we don't know what does. Turns out Diana was the queen of loungewear, not 2020.
GOODMOVE Cotton Crew Neck Sweatshirt, $25.00 Buy
GOODMOVE Cotton Rich Cuffed Joggers, $25.00 Buy
BERTIE Western Knee High Boots, $165.00 Buy
Diana's infamous Black Sheep jumper was made by Warm & Wonderful but preppy Manhattan label Rowing Blazers has teamed up with the OG designers to relaunch it. Team yours with white collars and loose trousers, too.
Warm & Wonderful x Rowing Blazers Women's Sheep Sweater, $250.00 Buy
Topshop White Embroidered Peter Pan Collar, $15.99 Buy
Jigsaw Fine Drill Wide Trouser, $98.00 $39.00 Buy
Unexpected styling trick from the Diana archives: throw a vintage baseball jacket over a bodycon dress, add gold hoops and you're good to go.
Astrid & Miyu Mystic Simple Hoops in Gold, $49.00 Buy
The Requirement Room Vintage 1970s Varsity Letter D Letterman Jacket, $62.00 Buy
Zara TRF Fitted Dress, $12.99 Buy
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