Almost 26 years after her death, Princess Diana remains a style icon, her influence evident on the SS23 catwalks, from pointed shouldered blazers at Balenciaga to prim tweed at Chanel. But, there is one trend that is proving more popular than the rest, and that is the preppy trend.
Originating in the United States, preppy originally referred to the style of those who attended the Ivy League and prep schools (hence the name “preppy”). The unofficial uniform for these wealthy students consisted of polo shirts, cable knit sweaters, 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, plaid prints and a more athletic 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 took off in the ’80s, as designers such as Tommy Hilfiger, Calvin Klein and Lacoste championed the look and Princess Diana became the poster child for the trend.
His v-neck cricket sweaters, worn long on the body and layered under powerful blazers were a clash of business and sportswear. Likewise, her baseball cap and baggy trousers tucked into cowboy boots represent another clash, that of Diana’s desire to be both normal in her role as a mother, yet privileged as Princess of Wales. .
A smiling Princess Diana leaving Chelsea Harbor Club in 1995 wearing her iconic oversized American sweatshirt and fucsia pink cycling shorts
This Princess Diana lookalike sweatshirt is available on Shein’s website and tagged USA Sweatshirt for £8.99
Princess Diana in her gray and crimson Ivy League Harvard sweatshirt after a training session at Earls Court in 1997
This almost identical gray and crimson Harvard sweatshirt is available at ASOS for £35 this season
Diana’s fashion was always intentional as the young princess recognized the sartorial significance clothes could have. Her choice to debut her famous “revenge dress” was no coincidence, after all.
Aside from prom dresses, she’s been photographed the most in activewear – her go-to uniform consisting of a slogan sweatshirt, cycling shorts and calf-length socks worn with matching white trainers to a big red overcoat which is very trendy at the moment.
Perhaps an attempt to assert some normalcy against the rules and regulations she had to adhere to as a member of the royal family, but she maintained a sense of glamor and royalty even in these sportswear ensembles with the designer handbags and sunglasses she accessorized.
It’s no wonder Diana was so taken with the preppy trend, rooted in American symbols of privilege while embracing a casualness traditionally not accepted in the British royal family. She possessed a sense of contradiction in her life as well as in her clothing.
Princess Diana running to school in April 1989 wearing a navy baseball cap and oversized blazer which is also very fashionable this year
This Ralph Lauren logo-embroidered cotton cap is available on the website and in stores for €45.00
Princess Diana wore this iconic outfit in Scotland in 1988. The electric jacket with shoulder pads and oversized cricket jumper are one of the best ‘preppy’ looks this summer.
This must have preppy Ecru Cricket Jumper for £60 is available from the John Lewis website
Diana wore that oversized red coat that is all the rage this season and white Reebok tennis socks against her strong brown legs in 1996
This £48 oversized red coat is almost identical to the one Princess Diana wore in 1996 and was sold on the ASOS website.
Princess Diana gives Prince Harry a layered back at Smiths Lawn Polo in Windsor in 1987. She wore her Mickey Mouse sweatshirt with jeans and always looked chic
This White Mickey Mouse Crew Neck Sweatshirt is £14.00 at New Look
Princess Diana in her navy oversized sweatshirt and white cycling shorts seen at the Chelsea Harbor Club in 1996
Princess Diana leaving Chelsea Harbor Club in 1995 wearing her iconic Navy Virgin Atlantic sweatshirt which she always wore and her favorite white cycling shorts
This navy and red Wellness sweatshirt from Sporty and Rich is a bit pricey at £148 but definitely has the ‘preppy’ look
This whole Pretty Little Thing look could be straight out of the early 90s with the white cycling shorts, a large sweatshirt for £22 that says ‘Better Days Ahead’ on the back and cotton sports socks.
While the preppy trend continued to adapt and change over the following decades, the current preppy trend is more synonymous with that of the late 80s and early 90s identity.
Today’s hot preppy look made its debut on the Fall/Winter 22 runways as the likes of Louis Vuitton, Miu Miu, Gucci and Ralph Lauren sent models down the runway wearing ties, sweaters V-necks, plaid suits and pointed shoulders galore. Make no mistake, preppy chic is set to continue this season, but with an updated, modern twist.
So before you dust off your headband, don your tartan plaid miniskirt and buckle up your Mary Janes, the SS23 way to go preppy is more laid back Diana cool than polished Sloane ranger. If you’re going the prim and proper way, you’ve missed the mark.
It’s no surprise that this trend is coming back into fashion. It is a timeless and classic look that gives a polished feel to the wearer, allowing almost anyone to look good in style. Comprised of wardrobe staples, blazers that transition seamlessly from office to night out, and cricket sweaters that refresh your weekend look, whether simply tied over the shoulders or worn as a must-have layer.
Worn together they can give off a preppy feel, but worn separately they are simply the basics of a capsule wardrobe. Unlike other up-to-the-minute trends, preppy clothing is available on the high street, allowing shoppers of all budgets to dabble in the look. And because you’re buying highly functional staples that possess both versatility and longevity, it may be worth splurging on a quality item like the Circa 1987 Princess.