Lady Di, Princess Di, “the People’s Princess”, Diana; no matter what name you know her by, Diana Spencer was and still is one of the most iconic and well-known individuals in the history of the British monarchy. Praised for her charity work, charm, and down-to-earth disposition, stating that the late Princess of Wales was adored by her people would be an understatement. She left a lasting legacy not only as a Princess, but simply as Diana: a kind-hearted soul whose benevolence changed Britain for the better. 

One well known aspect of Diana’s legacy falls within a slightly unexpected realm: Fashion. Diana Spencer’s style, from lavish gowns to chic model-off-duty looks, has become an undeniable aesthetic in the fashion world. Her looks are the definition of timeless and natural beauty, and have been recreated time and time again by celebrities and everyday folks alike trying to achieve her effortless style. Get these classic Diana Spencer looks that have made their way from ‘90s England all the way to 2022.

The Biker Shorts + Crewneck Combo

The iconic “Diana leaving the gym look” is one of her most casual, yet most well known looks to date. In it, she sports sneakers, biker shorts & graphic crewnecks, usually tied together with an elegant handbag and pair of sunglasses. Biker shorts, a staple of the 90’s that were popularized by Diana, returned to their former glory in 2021, and have remained steadily popular since. 

Jackets & Blazers 

Blazers were a well known staple in Diana’s wardrobe. Pairing them with just about anything from skirts, to jeans, to slacks, big jackets and sleek sharp blazer looks never failed to take one of Diana’s more casual outfits to a whole new level. Currently, blazers have become more and more prominent outside of the business-professional world, popping up in fashion trends everywhere starting around 2021.

The Revenge Dress

If there is one look Diana is known for, it's the Revenge Dress. In November of 1994 after Prince Charles publicly admitted his affair with the now current Queen Consort Camilla, Diana attended an event for Vanity Fair wearing a short, off-the-shoulder black dress that both shocked and delighted viewers at the time. Since then, the concept of both the Revenge Dress and the Little Black Dress has been merged, mixed, and re-created time and time again.

Button-ups & Belts 

The chic combination of button-ups, belts, and the classic ‘90s mom jeans was often a look sported by Diana. While on the slightly more casual side, this combination is a very well known part of Diana’s wardrobe as it captures a timeless ‘90s style that will continue to re-enter current fashion trends.

The Stylish Sweater

This list would not be complete without mention of Diana’s iconic statement sweaters. Often giving off the hand knit wool look, Diana’s sweaters ranged from chique and understated to colorful and over-the-top. Perhaps her most classic statement sweater to date is the ‘Black Sheep’ sweater, a red woolen crewneck printed entirely with small white sheep with one black sheep standing out against the group. This is thought to be Diana’s discrete commentary on being the “black sheep” of the royal family as it is widely known that she never felt truly accepted within their circle. This sweater, as well as many of Diana’s others, has been re-printed and recreated across various sites and distributors in an attempt to mimic her iconic and unique style.

From her chic button-ups and belts to her stylish crewneck and biker short combos, Diana Spencer’s ageless looks do not appear to be leaving the fashion world any time soon. With a style that transcends time comes a legacy that has and will continue to impact the world of fashion for years to come.

Written by Emma Ehle, Photography by Sanjana Bejawada, Social Media by Taylor Gustafon