7 Princess Diana looks you could still wear now - and how to recreate them

Think Diana, Princess of Wales, and though fashion icon would probably come to mind, you might assume that her style belongs firmly in the Eighties and Nineties archives. From puffball skirts to exaggerated shoulders and frills galore, Diana was famously unafraid to embrace the biggest trends of the day, many of which have now been consigned to the fashion history books, unlikely ever to be revived again.

And yet, there's a slew of the late Princess’s outfits that would look as good now as they did when she first wore them. Indeed, many have even influenced current trends; think of cycling shorts, a look inspired by the Nineties sportswear look which Diana epitomised, or cowboy boots, which she wore off-duty to add personality to jeans or tracksuits.

On what would have been Diana’s 59th birthday, these are seven of her classic outfits which are perfect contenders for re-creation in 2020...

The polo skirt and shirt

This has to be one of my favourite ever Diana looks - the jumper casually tossed over the shoulders makes it apparently effortless but note how she has picked out the red to tie it all together with just enough regal polish. A floral midi skirt is a timeless investment - opt for a style that’s not too full, like this £65 button-through from And Other Stories - and pair with a statement white blouse (follow Strange Moon Vintage on Instagram for daily drops of similar styles), then perfect the artful sweater toss.

The cool kaftan

The Princess may have worn this crisp Catherine Walker kaftan as a sign of sartorial respect during a visit to Saudi Arabia, but it’s still the ideal look to channel on a hot summer’s day. Arket have several modern takes to try, from this burgundy abstract floral design (now £45) to this sleeveless blue style (£99). If it's a cooler day, wear with white jeans for a further twist on Diana's outfit.

The slip dress

One of Diana’s most famous post-royal fashion moments was when she attended the Met Gala in New York as the first person to wear John Galliano’s designs for Dior. He created this navy silk slip dress, a rather risqué choice for a one-time HRH and mother to the future king, but it was a seminal moment in Diana’s bid for independence, carving out a new international and glamorous image for herself.

A navy silk dress remains a classic today - you could wear it like Diana, dressed up with pearl jewellery, or pare it back with minimal adornment and simple sandals or trainers. Whistles’ beautiful panelled dress has just been reduced to £109 in the sale.

The gym look

For all Diana’s ballgowns and dialled-up daywear, it is her gym style which still resonates most, nearly 23 years on from her death. Her favoured combinations of logo sweatshirts, cycle shorts, trainers and designer bags, worn for her visits to Chelsea’s Harbour Club, have found a new generation of Millennial and Gen Z fans who are inspired by this early example of luxe athleisure.

Look to Ninety Percent for sustainably-made cycle shorts (£80) and team with a vintage sweatshirt - Beyond Retro has an excellent selection.

The sundress

Has there ever been a time when a floral dress of some description wasn’t a perfect summer style solution? Certainly, Diana had a host of options in her repertoire, just as the Duchess of Cambridge does today. This bright painterly design was perhaps one of the Princess’s best known, and a striking choice for a visit to Nigeria.

Last week, Kate debuted a fresh floral frock by Indonesia-based sustainable label, Faithfull The Brand, her latest take on the eye-catching sundress trend; this £189 design by the same label will conjure modern Diana vibes.

School run chic

While many yummy mummies might recoil at the idea of doing the school run in a grey tracksuit, Diana was able to lend the ensemble fashion edge by pairing it with a baseball cap, blazer and cowboy boots.

It may take a brave woman to recreate this formula head-to-toe (though, brava, if you’re up for giving it a try) so instead take inspiration from the styling and key pieces - tuck jeans into cowboy boots (see Rokit for the best vintage buys) or offset casual loungewear with a smart jacket, a great way to repurpose more dressed-up pieces if you're not heading to the office at the moment.

Shirt and chinos

So simple yet so expertly executed. In her 30s, Diana learnt that less can be more, and that it’s how you wear an outfit that’s important. This laid-back combination of chinos, a white shirt and Tod’s suede driving loafers is a lesson in making casual look polished; note the sunglasses hooked into the shirt, the classic gold jewellery and nonchalantly rolled shirt sleeves.

You could source this outfit anew entirely from Massimo Dutti, Zara's big sister label which specialises in refined, grown-up style; wear its £49.95 linen shirt with its stone jeans (also £49.95) and caramel loafers (on sale at £44.95)

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