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Princess Diana’s Blazer And Jeans Era Was By Far Her Best

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When pictures emerged of Elizabeth Debicki wearing Princess Diana’s infamous revenge dress on set, we knew that season five of The Crown would deliver royally good fashion. But it’s the later images of Debicki wearing the uniform Lady Di honed for herself some years after that Christina Stambolian dress stole headlines which caused us to double take. The likeness between the actor and princess is really very good. And the costumes are an excellent reminder that the period during which Diana had distanced herself from royal protocol was when she looked her most confident and, arguably, her most stylish.

Elizabeth Debicki doing Di’s tailoring era now.

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From Balmoral to London, Di did private jetting in business-chic style in August 1992.

Julian Parker

Diana’s armour in the late ’90s revolved around boxy blazers, crisp shirting and slim-cut jeans, worn with Tod’s Gommino loafers and a Dior Lady Di bag. These looks, worn most often on her Red Cross visits abroad and to and from the Wetherby school gates, signalled a certain capability and dignity without ever looking too calculated. “She used clothes to [send a] message very powerfully,” says Amanda Wakeley, the woman behind some of the beautifully-cut jackets fashioned to make Diana feel important and self-assured. Wakeley’s secret? Lining the sleeves with silk so her suits felt impossibly soft.

Diana dressing down her favourite blazer with Superga plimsolls in Angola, January 1997.

Pool/Tim Graham Picture Library

After a long-haul flight to Sarajevo, Di still radiated professionalism thanks to her signature, strong-shouldered armour, August 1997.

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In Diana’s hands, the blazer became more than just a signifier of “business”. She veered from her so-called “Sloane Ranger” preppy style and paired her jackets with long-line pleated skirts and pumps; tracksuits and cowboy boots. She was seminal in propelling the blazer forward as an all-rounder, not just something to take to work. Which is why the images of Debicki on set in Croydon resonate. We can imagine wearing The Crown’s version of Diana’s business-casual, like many of the princess’s famous looks, now.

Looking smart at the Grand Prix in July 1994.

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Dark tailoring for the win in London, March 1997.

Tim Graham

If the paparazzi shots are anything to go by, Debicki has nailed the ease with which Diana carried herself during this period. “In the beginning, she was sort of wearing a costume,” explains Wakeley. “Her style became effortless as the years ticked on.” While modern-day royals certainly deliver polish, no one has quite mastered the throw-on-and-go insouciance of the Diana blazer era and that’s why we still put her on a pedestal. 

Does shopping in Knightsbridge get any chicer? October 1994. 

Julian Parker

The school-gates look engrained in the public psyche, April 1989.

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Diana, Princess of Wales in Dior.
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