How To Execute Winter’s Trickiest Boot Trend With Princess Diana Flair

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Diana, Princess of Wales’s style legacy lives on through her campy knitted jumpers, monster-collared blouses and the trouser-boot tuck. The latter divisive styling flourish has seen a resurgence this season owing to the popularity of Chanel’s pirate boots (yes, swashbuckling got stylish) and Wellington boots (the tall outdoorsy update to Bottega’s cult stompers). But for some, the classic French-girl fold of trouser into boot (see also Isabel Marant, who is a transeasonal supporter) has never fallen out of fashion.

Proof that the Diana tuck is in the realm of bourgeois Parisian style has consistently been provided by Hedi Slimane since he got into his stride at Celine. The creative director reconnected the house with its roots and the polite, elegant fashion of its founder Céline Vipiana. Among the hallmarks of the brand–such as culottes, pussy-bow blouses, capes, pleated knee-length skirts and horsebit belts–are glossy knee-high boots. When one of the City of Light’s leading fashion voices shouts, others listen.

Princess Diana at the Guards Polo Club in 1987.

© David Crump/Daily Mail/Shutterstock

But if the #oldoldCeline look is synonymous with upper-class polish, 2020’s boot tuck is a little more free form owing to the boots on trend – and our reliance on loungewear. British Vogue deputy editor and fashion features director, Sarah Harris, is firmly in this new wave of trouser cinchers. “Admittedly, I never used to be in favour of this look because it was the epitome of Sloane–the neat blue jean, smart shiny black riding boot, tweed blazer and knotted pashmina around the neck—but with a few style nuances it’s become one of my favourite looks to emerge in recent seasons,” she explains.

Princess Diana on the school run in 1986.

© Steve Back/Daily Mail/Shutterstock

Harris has a few rules for executing a non-Sloaney tuck that has the louche flair of Princess Diana on the school-run circa the late ’80s. “Firstly, never choose a skinny jean, choose a straight-leg or slim boyfriend style,” advises Harris. “Although skinny jeans are a no, black leggings will always look great, paired with a huge sweatshirt or a cashmere cardigan, or a mannish white shirt and an oversized blazer. I think the idea of the styling is that it has to look nonchalant, the tuck-in has to look rushed, like you just stepped into the boots and ran out of the house. When it looks too neat, it looks too thought-out, that’s when it falls apart.” 

Princess Diana at the polo in 1988.

© Getty Images

Camille Charrière, a staunch supporter, concurs: “I think it can look extra chic tucked into a crisp white high-waisted trouser, but can also work over any kind of athleisure when running out the house for an errand. I love tucking my denim into cowboy boots (very Lady Di) and my leggings into chunky high boots for when I can’t be bothered to put a look together.” Use the picture of the late Princess of Wales with her pale trousers tucked in her signature brown boots – which is firmly ingrained in the cultural psyche and has been reshared more than a few times around the airing of season four of The Crown – as a failsafe template.

Blanca Miró wearing Chanel’s pirate boots.

© Edward Berthelot

“Chanel’s pirate boot is probably one of the most versatile boots of the season,” advises Harris. “Virginie Viard showed the style with everything from trousers to day dresses to evening wear, so it’s no surprise that it’s also the easiest boot to scrunch trousers into. The shape is ideal; they’re lifted slightly on a heel which will always lengthen legs, the opening is wide enough to tuck a boyfriend jean in and the turned down cuff on them adds another element of interest to the proportion.” Priced at £1,600, the Chanel trouser tuck is an investment for life. But, others, such as Charrière’s preferred Coperni Bridge boots (£532), still have the royal stamp of approval.

Camille Charrière modelling Coperni boots outside the Hermès show at Paris Fashion Week.

© Christian Vierig

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