Princess Diana remains a style icon even now

Princess Diana remains a style icon even now. It’s a quarter of a century since she left us but her off-duty fashion is everywhere, in the shops and on the catwalk – and has never looked so eerily familiar

  •  Her ‘preppy’ look was named after upmarket American ‘preparatory schools’
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Almost 26 years after her death, Princess Diana remains a style icon, her influence evident on the SS23 runways from the sharp, shoulder-padded blazers at Balenciaga to prim tweed at Chanel. But, there’s one trend proving more popular than the rest, and that’s the preppy trend.

Originating in the United States, preppy initially referred to the style of those attending Ivy League and preparatory schools (hence the name ‘preppy’). The unofficial uniform of these wealthy students consisted of polo shirts, cable knit jumpers, loafers and of course, crew neck sweatshirts emblazoned with each university’s name and logo – something Diana herself wore in 1997 when she was photographed leaving the gym in a Harvard sweatshirt.

The 1950s saw the preppy style expand to include knitted twin sets, sweater vests, check prints, and a more athleisure influence in the form of rugby shirts, these garments all acting as visual signs of heritage, wealth, and influence.

There’s no denying that preppy chic really came into its own in the 80s though, as designers such as Tommy Hilfiger, Calvin Klein and Lacoste championed the look and Princess Diana became the poster girl for the trend. 

Her v-neck cricket jumpers, worn long on the body and layered beneath power blazers were a business-meets-sportswear clash. Similarly, her baseball cap and billowing trousers tucked into cowboy boots represents another clash, that of Diana’s desire to be both normal in her role as mother, but privileged as the Princess of Wales.

A smiling Princess Diana leaving the Chelsea Harbour Club in 1995 wearing her iconic oversized USA sweatshirt and fucsia-pink cycling shorts

This  lookalike Princess Diana sweatshirt is available on the Shein website and labelled  USA Sweatshirt  for £8.99

Princess Diana in her ‘preppy’ Ivy League grey and crimson Harvard sweatshirt after a work out in Earls Court in 1997

This almost identical grey and crimson Harvard sweatshirt is available on ASOS for £35 this season

Diana’s fashion was always intentional as the young Princess recognised the sartorial meaning clothes could carry. Her choice in debuting her famous ‘revenge dress’ was no coincidence, after all. 

Alongside the ball gowns, she was most photographed in athleisure wear – her go-to uniform of slogan sweatshirt, cycling shorts, and mid-calf socks worn with white trainers teamed with a large red overcoat which is very on trend at the moment.

Perhaps an attempt to assert some normalcy against the rules and regulations she hat to adhere to as a member of the royal family, yet she maintained a sense of glamour and regality even in these sportswear ensembles with the designer handbags and sunglasses she accessorised with.

It’s no wonder Diana was so taken with the preppy trend, rooted as it is in American symbols of privilege while embracing a casualness not traditionally accepted in the British royal family. She possessed a sense of contradiction in her life as well as her clothing.

Princess Diana doing the school run in April 1989 wearing a navy blue baseball cap and an oversized blazer which is very fashionable this year, too

This Ralph Lauren logo embroidered cotton baseball cap is available on the website and in stores for £45.00

Princess Diana wore this iconic outfit in Scotland in 1988. The power jacket with shoulder pads and the oversized cricket sweater is one of the top ‘preppy’ looks this summer

This must have preppy Ecru Cricket Jumper for £60 is available on the John Lewis website 

Diana wore this oversized red coat  which is all the rage this season and white Reebok tennis socks against her strong brown legs in 1996

This oversized red coat which was priced at £48 is almost identical to the one Princess Diana wore in 1996 has sold out on the ASOS website

Princess Diana giving Prince Harry a piggy back  at the Smiths Lawn Polo, Windsor in 1987. She was wearing her Mickey Mouse sweat shirt with jeans and still looked chic

This white crew neck Mickey Mouse sweatshirt is £14.00 from New Look

Princess Diana with her navy oversized sweatshirt and white cycling shorts seen at the Chelsea Harbour Club in 1996

Princess Diana leaving the Chelsea Harbour Club in 1995 wearing her iconic Navy Virgin Atlantic sweatshirt that she always wore and  her favourite white cycling shorts 

This navy and red Wellness sweatshirt from the Sporty and Rich brand is a tad expensive at £148 but definitely has the ‘preppy’ look

This whole look from Pretty Little thing could be straight from the early nineties with the white cycling shorts, large sweat shirt for £22 saying ‘Better Days Ahead’ on the back and cotton sports socks

While the preppy trend continued to adapt and alter in the following decades, the current preppy trend is most synonymous with that of the late 80s and early 90s identity.

Today’s en-vogue preppy look was first debuted on the autumn/winter 22 catwalks by the likes of Louis Vuitton, Miu Miu, Gucci and Ralph Lauren who sent models down the runways decked out in ties, v-neck jumpers, check suits, and sharp shoulders galore. Make no mistake, preppy chic is set to continue this season, but with an updated and modern twist. 

So before you dust off your headband, pull on your tartan check mini skirt, and buckle up your Mary Janes, the SS23 way to do preppy is more laidback Diana cool than polished Sloane ranger. If you go down the prim and proper route, you’ve missed the mark.

It’s no surprise this trend keeps coming back in fashion. It’s a timeless and classic look that lends a feeling of polish to the wearer, allowing almost anyone to look good in the style. Comprised of wardrobe basics from blazers that transition seamlessly from the office to evening events, and cricket jumpers that provide a refresh to your weekend off-duty look whether simply knotted over shoulders or worn as a much-needed layer. 

Worn together they may exude a preppy feel, but worn separately they simply provide the foundations of a capsule wardrobe. Contrary to other trends of the minute, preppy clothing is available across the high street allowing shoppers of any budget to get in on the look. And because you’re buying high-functioning staples that possess both versatility and longevity, it may be worth splurging on a quality item take your lead from the Princess circa 1987. 

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