Recreate Princess Diana’s Most Iconic Styles and Looks From Her Black Sheep Sweater to Revenge Dress
The people’s princess was ahead of her time when it came to trends we see today
There’s no denying that Princess Diana was—and still is considered to be—an icon and cultural phenomenon. From entering into the Royal Family at just 20 years old to her admirable advocacy and philanthropic work for AIDS, Princess Diana truly was America’s princess (despite the Royal Family being based in the U.K.). She was deeply beloved for many reasons and had constant eyes on her at all times until she tragically passed in 1997. She wasn’t just loved for her charming persona and warm spirit though—she also served as major style inspiration from the ‘80s to today. Keep reading for the best Princess Diana style moments, and how you can recreate her most iconic looks today.
What was Princess Diana’s style?
Princess Diana was the queen of street style, and truly a fashion icon. She was looked to in the 1980s for outfit inspiration, and now, 30+ years later, her style still reigns supreme and inspires Gen Z, millennials and Gen X alike. Her casual-cool street style mixed with her sophisticated royalty-worthy outfits made Princess Diana the ultimate “it” girl.
Princess Diana’s street style was often met with oversized crewnecks, comfy biker shorts, sweaters layered over collared button-down tops, casual denim and shoulder-padded, oversized blazers. A lot of the looks we saw her wearing in the ‘80s are now considered trendy four decades later—many, if not all, of the pieces just listed are commonly worn today.
As for Princess Diana’s more “dressy” outfits and formal style, she loved wearing skirt and blazer two-piece sets, along with straight and fitted T-length dresses. She almost always had a pair of earrings in, usually chunky studs or pearls. She’s also famously known for her “revenge dress,” a sexy, black, off-the-shoulder cocktail dress that was paired with a statement pearl choker, sheer black tights and heels, which she stepped out in the night that her husband, Prince Charles, admitted on television he had an affair.
11 best Princess Diana style moments and how to get the look
Keep reading for the most notable Princess Diana outfits and street style, as well as how you can recreate the looks today.
Princess Diana’s infamous black sheep sweater
This sweater that Princess Diana wore in 1983 was more than just stylish—it symbolized something greater. White sheep decorate the majority of the sweater, aside from one notable black sheep. A “black sheep” refers to someone who doesn’t necessarily fit in with their family or social group. Princess Diana wasn’t afraid to speak her mind and do things out of the norm, which could make her the Royal Family’s “black sheep.”
Get the look: You can recreate this look identically with Rowing Blazers Warm & Wonderful “Diana Edition” Cotton Sheep Sweater, which is the exact brand of the OG sweater Princess Diana wore. Or, for a more affordable alternative, try A1 Jackets Princess Diana Black Sheep Sweater on Amazon. Pair it with relaxed white pants and red or black flats. Or, for a look that’s not identical but more “inspired by” the sweater, we like L’Oeuf Poche Diana Sweater.
Princess Diana’s “Revenge Dress”
As mentioned above, this is one of Princess Diana’s most famous looks. Her “revenge dress” was plastered all over news headlines, and seemed to be in response to Prince Charles admitting his affair on television.
Get the look: A black, off-the-shoulder cocktail or evening dress is what you need to recreate this look. We like Norma Kamali Tara Side Drape Gown, which has the off-the-shoulder style, asymmetrical hemline and ruching similar to the original. Finish the look with a pearl necklace and sheer, black tights.
Princess Diana’s go-to biker shorts and oversized crew combo
Biker shorts may be trendy now, but they’re nothing new. Princess Diana often wore them in the ‘80s with comfy and cute oversized crewnecks. She liked to top the look off with scrunched crew socks and sneakers.
Get the look: You can channel this look with any pair of biker shorts and oversized sweatshirt. If you want this exact look, try Spiritual Gangster Love Sculp Seamless Rib Bike Shorts in “Neon Coral” along with TZshirts Fly Atlantic Princess Diana Sweatshirt.
Two-piece skirt sets
Princess Diana was known to wear skirt and blazer sets for more “dressy” or professional occasions. This pink set is so chic, and her chunky gold earrings elevate the look.
Get the look: What’s great about a skirt suit is it can be worn together or separately. Choosing a set in a fun shade adds a pop of color to your work wardrobe. Try Nipon Boutique Curved Collar Button-Front Jacket & Pencil Skirt Suit.
Statement sleeve blouses
A statement sleeve can take a blouse from drab to fab instantly. The ‘80s were all about padded shoulders and puff sleeves, which Princess Diana sported with many of her outfits. This black-and-white puff sleeve top showcased her fun-spirited style.
Get the look: Pair Mint Velvet White Polka Dot Ruffle Top with anything from black jeans to slacks or even a midi skirt.
Princess Diana’s oversized blazers
Again, Princess Diana couldn’t stay away from the padded shoulders that ruled the ‘80s. Oversized blazers with shoulder pads were a huge trend during this decade, and Princess Diana followed suit. In this chic look, she’s wearing a green oversized blazer over a simple white turtleneck with white jeans. She broke up the white with a brown belt, and accessorized with a brown and white tote and loafers.
Get the look: Take your favorite white or off-white long-sleeve and tuck it into white jeans or slacks. Layer Endless Rose Oversized Notched Collar Blazer over the top, put on a brown belt, slip into a pair of brown and white penny loafers and add a tote.
Varsity jacket meets modern bomber jacket
Letterman jackets were another major trend of the ‘80s, and have a similar fit to the modern-day bomber jacket we see trending. Here, Princess Diana sported a Philadelphia Eagles jacket over a black skirt and tights, making the typically dressy look more casual.
Get the look: There are so many ways you can recreate this look and put your own spin on it. Start with a black midi skirt and black top, or a black dress, over black sheer tights. For the jacket, wear your favorite sports team-themed varsity bomber jacket, or for a more affordable and versatile option, any standard, neutral bomber jacket works.
Princess Diana’s blazer and denim combo
A graphic crewneck pairs well with everything from lounge pants to denim, as Princess Diana proves with this look. For an extra layer, toss on an oversized blazer or jacket.
Get the look: For a comfy-casual look that’s just a bit more elevated, look no further than a cozy crewneck, your favorite jeans and a blazer. And to finish off the look, toss on a baseball cap and a pair of tall brown boots.
Princess Diana’s blue chiffon dress moment
At the Cannes Film Festival in 1987, Princess Diana arrived in this gorgeous baby blue, chiffon gown. The neck scarf is a trend we’re starting to see come back, and adds the most elegant touch.
Get the look: For a blue chiffon dress similar to Princess Diana’s, we like Birdy Grey Grace Convertible Dress With Slit in “Ice Blue.” For the neck scarf, try Wander Agio Long Scarf in “Light Blue.”
Polo club chic
Another baby blue moment, Princess Diana looked sophisticated in blue pinstripe straight-leg pants paired with a white blouse. You could wear this outfit to the office, a daytime outing and more.
Get the look: Abercrombie & Fitch Harper Tailored Linen-Blend Pant are the perfect pinstripe pant option and are lightweight and comfy thanks to the linen-blend fabric. Wear them with Zara Peter Pan Collar Blouse, and add a skinny white belt.
Straight-fitting cocktail dresses
A simple cocktail dress was a staple in Princess Diana’s closet and often had a straight-down fit. This floral number was worn by the princess in June 1997, making it the perfect summer dress.
Get the look: For a similar look, we recommend Milumia Floral Ruched Dress on Amazon. Wear it to a cocktail party, date night and other fancier occasions.
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