Kate Middleton and Princess Diana: The Two Princess of Wales’ Best Style Twinning Moments

Princess Kate and Princess Diana

JAYNE FINCHER/GETTY ; KARWAI TANG/WIREIMAGE


As Kate Middleton steps up into a new royal role as the Princess of Wales, she follows in the fashionable footsteps of another Princess of Wales — her mother-in-law, Princess Diana — and occasionally pays tribute through dress.

“I think we have seen lots of examples where the reference is very intentional and I think that Kate uses fashion to pay tribute to Diana in a very positive way,” Bethan Holt, Fashion News and Features Director of The Daily Telegraph, tells PEOPLE.

Holt points out that it was Kate’s husband, Prince William, who suggested the idea for Diana’s charity gown auction in 1997, noting that the new Prince of Wales “has always been very conscious of his mother as a style icon.”

“I think that William and Kate between them might have decided that actually on some occasions it’s a really nice thing for Kate to reference the fact that Diana is still a fashion muse today and to do that through her own clothes,” she says.

Kate Middleton, Princess Diana

Kate Middleton; Princess Diana. CHRIS JACKSON/GETTY; TIM GRAHAM PHOTO LIBRARY VIA GETTY

Polka dots are always in style for the Princess of Wales! Kate looked timeless in the classic print at Royal Ascot in June, channeling Diana’s polka dot look at the Epsom Derby (another equestrian event) in 1986.

Kate even completed the look with an angular hat and pearl drop earrings, as her late mother-in-law did decades before.

princess diana; kate middleton

TIM GRAHAM PHOTO LIBRARY VIA GETTY ; ANWAR HUSSEIN / ALAMY

“What’s really key about these times when Kate references Diana, it’s not like a costume. She brings it right up to date so she makes it look relevant for now,” Holt, the author of The Queen: 70 Years of Majestic Style, notes. “She’s not doing an ’80s power shoulder or a puff ball skirt, she’s making it look sleeker and more contemporary. She makes it her own without looking like she’s playing ‘dress up as Diana.’ “

Kate made black watch tartan look fresh during an outing in Scotland in 2019, evocative of the plaids Princess Diana often reached for in the ’80s and ’90s.

princess diana; kate middleton

JAYNE FINCHER/PRINCESS DIANA ARCHIVE/GETTY; MARK CUTHBERT/UK PRESS VIA GETTY

Diana stylishly stepped out in a structured suit with frogging and epaulettes to visit the Royal Military Academy Sandhurst in 1987, and Kate has copied the same military inspiration for related engagements.

Fashion fans know that Kate increasingly channeled Diana in recent years, which Holt says is a sign of confidence.

“I think for a long time she was a little bit reluctant with her style, and the reasoning behind that was meant to be that Diana was this huge global style icon and those were really big shoes for Catherine to fill,” the fashion director says.

princess-diana-3

DOMINIC LIPINSKI/PA IMAGES/GETTY; TIM GRAHAM/GETTY

“For a few years at the beginning of her marriage, she was very tentative and we didn’t see her doing it very much,” Holt says of the deliberate tributes. “As she’s become more confident in her own style, knowing what works for her, she’s then been able to incorporate those Diana moments into her own wardrobe and she’s done it in a way that really makes sense.”

Kate popped in a red and white houndstooth coat dress while pregnant with Prince Louis during a royal tour of Sweden and Norway in 2018, nodding to a statement jacket of Diana’s in the early ’90s.

princess diana; kate middleton

FOX PHOTOS/HULTON ARCHIVE/GETTY; SAMIR HUSSEIN/GETTY

“The ’80s look is totally back in fashion, so even if you didn’t get the Diana reference, then Kate would also be looking fashionable in wearing those outfits. I think it shows her acknowledging that fashion is still obsessed with Diana,” Holt says.

Diana was all smiles in a sailor suit in 1981, which Kate made modern with a sweater set in 2011.

Princess Diana, Kate Middleton

Princess Diana; Kate Middleton. JAYNE FINCHER/PRINCESS DIANA ARCHIVE/GETTY; CHRIS JACKSON/GETTY

Kate lit up the world premiere of the James Bond film No Time to Die in a glittering long-sleeved gold gown in September 2021, calling back to Diana’s metallic moment at the 1985 London premiere of another Bond film, A View to Kill.

princess-diana-6

CENTRAL PRESS/GETTY;MARK CUTHBERT/UK PRESS/GETTY

From particular prints to certain silhouettes, Holt says Kate’s whole attitude to fashion is inspired by Diana.

“The look she goes for is very feminine. It’s not super-princessy, but she does dress in quite a traditional ladylike way which Diana was very well known for,” the expert says.

Here, the women twin in black strapless gowns on their way to evening events.

Duchess of Cambridge; Princess Diana

Princess Diana in 1981 and Kate Middleton in March 2022 wearing emerald green gala gowns. PA IMAGES/ALAMY STOCK PHOTO; ANWAR HUSSEIN/GETTY IMAGES

With her first state visit as the Princess of Wales set for November, Princess Kate will surely sparkle as Diana did before her.

“She can reinvent what looking like the Princess of Wales means, because if you say ‘Princess of Wales’ now, we still think of Diana, but in a few years we are going to be thinking of Catherine, which is quite phenomenal,” Holt adds.

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Princess Diana and Kate Middleton wearing the sapphire engagement ring by Garrard. CHRIS JACKSON/GETTY IMAGES; TIM GRAHAM/GETTY IMAGES

Fashion comparisons between Diana and Kate inevitably began over a decade ago, when Prince William proposed with Diana’s iconic sapphire engagement ring in 2010.

As she’s married into the royal family and risen through its ranks, Kate has always taken these analogies with grace, and will continue to as the new Princess of Wales.

Palace sources say that Princess Kate “appreciates the history associated with this role but will understandably want to look to the future as she creates her own path.”

Adds Jamie Lowther-Pinkerton, Prince William’s former private secretary: “She will do so with humility and by acknowledging the past but in her own way.”

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