Nearly 26 years after her death, Princess Diana remains a style icon, her influence evident on the SS23 catwalks, from the sharp, shoulder-padded blazers at Balenciaga to primitive tweed at Chanel. But there’s one trend that’s proving to be more popular than the rest, and that’s the preppy trend.
Originally from the United States, preppy initially referred to the style of those who attended Ivy League and prep schools (hence the name “preppy”). The unofficial uniform of 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.
In the 1950s, the preppy style expanded to include knitted twin sets, sweater vests, check prints and a more sporty influence in the form of rugby shirts, all of which act as visual signs of heritage, wealth and influence.
There’s no denying that preppy chic really came into its own in the 1980s, when designers like Tommy Hilfiger, Calvin Klein and Lacoste championed the look and Princess Diana spearheaded the trend.
Her v-neck cricket jerseys, worn long on the body and layered under power blazers, were a clash between business and sportswear. Likewise, her baseball cap and billowing trousers tucked into cowboy boots represent another clash, that of Diana’s desire to be both normal in her role as a mother, but privileged as the Princess of Wales.
A smiling Princess Diana leaves the Chelsea Harbor Club in 1995 in her iconic oversized USA sweatshirt and fucsia-pink cycling shorts
This lookalike Princess Diana sweatshirt is available on the Shein website and is labeled USA Sweatshirt for £8.99
Princess Diana in her ‘preppy’ Ivy League gray and crimson Harvard sweatshirt after training at Earls Court in 1997
This nearly identical gray and crimson Harvard sweatshirt is available this season at ASOS for £35
Diana’s fashion was always deliberate as the young princess recognized the sartorial significance of clothes. After all, her choice to debut her famous ‘revenge dress’ was no coincidence.
Besides the ball gowns, she was most photographed in casual wear – her go-to uniform of slogan sweatshirt, cycling shorts and half-high socks worn with white trainers along with a large red overcoat that is very trendy right now.
Perhaps an attempt to assert some normalcy against the rules and regulations she must abide by as a member of the royal family, she still maintained a sense of glamor and regality even in these sportswear ensembles with the designer handbags and sunglasses she accessorized with.
It’s no wonder Diana was so enamored 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 both in her life and in her dress.
Princess Diana did the school run in April 1989 wearing a navy blue baseball cap and an oversized blazer that is also very much on trend this year
This cotton baseball cap with embroidered Ralph Lauren logo 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 jersey for £60 is available on the John Lewis website
Diana wore this oversized red coat that’s all the rage this season and white Reebok tennis socks against her strong brown legs in 1996
Priced at £48, this oversized red coat is almost identical to the one worn by Princess Diana in 1996 and is sold out on the ASOS website
Princess Diana piggybacked Prince Harry in the Smiths Lawn Polo, Windsor in 1987. She wore her Mickey Mouse sweatshirt with jeans and still looked chic
This white Mickey Mouse crew neck sweatshirt is £14.00 from New Look
Princess Diana in her navy blue oversized sweatshirt and white cycling shorts seen at the Chelsea Harbor Club in 1996
Princess Diana left the Chelsea Harbor Club in 1995 in her iconic navy blue Virgin Atlantic sweatshirt she always wore and her favorite white cycling shorts
This navy blue and red wellness sweatshirt from the Sporty and Rich brand is a little expensive at £148, but definitely has the ‘preppy’ look
This whole Pretty Little Thing look could have been straight out of the early 1990s with the white cycling shorts, the £22 large sweatshirt that says ‘Better Days Ahead’ on the back and cotton sports socks
While the preppy trend continued to adapt and change 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 introduced to the Fall/Winter 22 catwalks by the likes of Louis Vuitton, Miu Miu, Gucci and Ralph Lauren. sharp shoulders galore. Make no mistake, preppy chic continues this season, but with an updated and modern twist.
So before you dust off your headband, throw on your plaid miniskirt, and strap on your Mary Janes, the SS23 way to act preppy is more laid-back Diana cool than polished Sloane ranger. If you follow the first and correct route, you have missed the target.
No wonder this trend keeps coming back in fashion. It is a timeless and classic look that gives the wearer a sense of shine, making almost anyone look good in the style. Consisting of basic wardrobes of blazers that transition seamlessly from the office to evening events, and cricket jumpers that freshen up your off-duty weekend look, whether simply tied over the shoulders or worn as a much-needed layer.
Worn together, they may exude a preppy feel, but worn separately, they simply form the basis of a capsule wardrobe. Unlike other trends of the moment, preppy clothing is available across the street, so shoppers of all budgets can get in on the look. And because you’re buying high-performance staples that have both versatility and longevity, it can be worth splurging on a quality item, take your example from the Princess circa 1987.