Though her life in the public eye lasted less than two decades, Princess Diana’s legacy as a style icon is as enduring as ever. Even decades after her untimely death, Diana’s looks remain timeless, and her go-to outfit formulas continue to inspire new generations.
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The late Princess of Wales had many iconic outfits befitting a royal, with crown jewels and pastel skirt suits. But the people’s princess wasn’t afraid to step out in more casual ensembles, too. Her contributions to style go far beyond diamonds and gowns, artfully mixing casual pieces with more formal ones, pairing blazers with baseball hats and jeans with Western-style boots. One of her most famous outfits, which paired bike shorts with a sweatshirt, even inspired the term Princess Diana weather, otherwise known as those 60-degree days when it’s warm enough to show your legs but cold enough to wear a sweater. And though her job called for prim and proper pieces, she never failed to infuse her own sense of style, choosing bold colors, prints, and silhouettes. The way she wore simple, tailored pieces like trousers, blouses, and button-downs created a blueprint for effortless elegance and what today might be called quiet luxury.
To channel the late princess’s iconic style, try these seven pairings.
Sweatshirt and Bike Shorts
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One of Diana’s most iconic contributions to style is her sweatshirt and bike short combo. She first debuted the look in 1995, but it’s proven timeless. The comfortable and universally flattering look makes the perfect transitional outfit.
Pearl Chokers
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Diana’s infamous revenge dress look wouldn’t be complete without the five-strand pearl choker she accessorized with. And though most associate the necklace with this outfit, it’s far from the only time she pulled out this accessory, or ones like it. Diana wore fitted pearl strands with dresses of all necklines and proved they can be worn with both daytime and nighttime looks.
Play with Polkda Dots
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Diana never shied away from a bold color or print, and polka dots were a favorite. Whether it’s a full polka dot ensemble or a small detail on a blouse under a blazer, the print exudes playful elegance. Diana wore it in particularly feminine silhouettes, like dresses and pussy bow blouses, and paired it with equally elegant accessories like pearl earrings.
Blazer and Belt Combo
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Great blazers were the backbone of Diana’s wardrobe. She often chose ones with shoulder pads and styled them with belts that cinched the waist, a play on proportions that creates an angular hourglass silhouette. Though the big shoulder and high waist combination is distinctly ’80s, it still works today.
Mix Casual Pieces With More Tailored Ones
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Diana’s formula for casual dressing included jeans and boots, a blazer and a baseball hat. Diana’s love for blazers knew no bounds, and her artful combination of more formal, tailored pieces with more casual ones is as timeless as it comes.
Color Blocking
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Never one to shy away from color, Princess Diana was known to pair contrasting colors like pink, red, purple, and black. Color blocking, which is largely attributed to the artist Piet Mondrian, first took over fashion in the 1960s, but it resurfaces every few decades. To put a Diana spin on the technique, choose tailored jackets and dresses.
Colored Tights
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One of the royal family rules is that tights must be worn with skirts and dresses, and Diana didn’t limit herself to black or tan stockings. She matched her stockings to her dress, switching out red, brown, and white varieties. Diana was partial to sheer stockings, but more opaque styles worked, too.
