Princess Diana first entered the public eye in the '80s. Even early on, it was easy to tell she was super fashionable. But as she found her voice and her own way deviate from the strict rules of the monarchy, she came more into her own style, as well. Princess Diana's '90s fashion was amongst her best. She was bolder and more daring, taking all kinds of style risks to stay on trend.
As the '90s styles come back now, much of what the Princess of Wales wore in that decade is popular again. For instance, Hailey Bieber recently did a Diana-themed photo shoot replicating her old looks. Just goes to show how iconic her style was then, and how it remains a large part of her legacy today.
We've rounded up 20 of the princess' best '90s outfits that personify the decade's trends. Just don't be surprised if something seen here is also in a store window in 2021.
Eagles Jacket
The Philadelphia Eagles are an NFL team, but British-born Diana decided to sport the coat anyway. She paired the oversized jacket with a sleek black dress and a wide belt. That combo of bulky and fitted was very '90s, and it doesn't surprise us that Diana was among the early '90s trendsetters with this 1991 outfit.
Neutral Tones
While the 1980s were all about bright neon colors, color palettes used for fashion in the 1990s were much more natural and earthy. The princess nailed this style switch during an April 1991 trip to Brazil where she donned this tan skirt and blouse. She also worked in two other staples of the decade: flowy skirts and belts.
Pastel Floral
The colors on this dress are also more muted than they would have been in the '80s. And the flowers are more realistic than the abstract patterns seen in the previous decade. Pairing the outfit with a simple pearl necklace and earrings tied the whole look together. Meanwhile, Diana's companion, US first lady Barbara Bush, looks like she's still trapped in the '80s.
The Perfect Blazer
As '90s fashions come back into style now, this outfit would be just as acceptable today as it was in 1991 when the princess wore it. Everything from the mint color of the blazer to its simple check pattern to her basic black dress fit the decade perfectly. She wore this to visit Niagara Falls with her young sons.
Keeping It Casual
The baggy T-shirt tucked into the mom jeans with the leather belt is very 1992. The princess was one of the first royals to really show off her casual wardrobe in public, and fashionistas everywhere are better for it. Diana really was so stylish that she could pull off both an evening gown and a T-shirt with stars printed on it. There are no rules when it comes to her royal wardrobe.
Jean Jumpsuit
In 1993, Diana took her sons skiing in Austria, and they bundled up in super '90s outfits. The princess wore a chic denim jumpsuit coupled with a belt, white boots, and a trendy leather jacket. And then her sons both had those classic blue and purple windbreakers that it seems like every child wore back then. Iconic.
New Take on the Drop Waist
The '80s were known for drop-waist dresses, but the '90s put a new spin on the idea with super long blazers. It was the same general silhouette done in a new way. Diana paired her pastel blue blazer with a long pleated skirt and matching heels. Also look how little Prince Harry was here. It was 1993, so he was just 8 years old.
More Skiing Style
Vacation Diana is honestly a whole mood. This photo was taken in 1994, and the princess is totally rocking her oversized turtleneck tucked into her black leopard print pants. We love that she was unafraid to wear an animal print even while representing the royal family. Diana walked so Kate Middleton could run in her leopard print skirt.
Menswear
The third wave of feminism kicked off in the '90s, and it saw many women choosing to focus on their careers instead of or while having families. Fashion trends reflected this, with more women wearing traditionally "masculine" clothes. Meghan Markle is great at pulling off the menswear style now, and Princess Diana was back then.
Her Revenge Dress
This sexy black gown was nicknamed "the revenge dress," because Princess Diana wore it after Prince Charles publicly admitted to having cheated on her. She showed the whole world what he was missing out on. This outfit is also spectacularly '90s between the black pantyhose and pearl choker necklace.
All '90s, All the Time
Today's Instagram influencers are probably drooling over this chic 1994 outfit that Diana threw together. It's got all the '90s hallmarks — a turtleneck, neutral colors, a blazer, a belt, chic sunglasses, and loafers. If we had to describe that decade's fashion to someone and could only use one image, it would be this one.
Practically Inventing Athleisure
Today, athleisure is everywhere — especially after we just spent a year inside our houses. Who needs real pants or tight-fitting tops when we can wear stretchy bike shorts and oversized sweatshirts? It's that combo of baggy and fitted again. Diana pioneered this look for when she went to the gym, as she was one of the first royals to use a public gym.
Silky Blue
While the '90s didn't rely as much on bright colors, satin and silky materials were often used to help dresses make a statement. This gown is a Versace design that Diana wore in 1996 when attending a dinner in Sydney, Australia. She kept her jewelry to a minimum to show off her asymmetrical neckline and let the fabric shine on its own.
Stripes on Stripes
Patterns in the '90s were more streamlined, like pinstripes and checks instead of the big colorful shapes of the 1980s. Diana wore this striped blazer with a matching striped blouse while speaking on behalf of one of her charities in 1996. The outfit is serious and professional while still being fashionable.
Met Gala Slip Dress
In 1996, Princess Diana attended the fashion event of the year — the Met Gala thrown by Vogue editor Anna Wintour. The stylish princess picked a super '90s outfit to wear: the slip dress. It was a pretty daring choice, considering that it looked like lingerie. But Diana has never shied away from taking fashion risks.
Monochrome
Outfits that are all one color are trendy again, but Diana first wore this all-black ensemble in 1997. Her oversized blazer stands out the most, as do her kitten heels. Unlike the Duchess of Cambridge, Diana tended to prefer flats or low heels to the sky-high stilettos that Kate often wears today.
Chic Pantsuit
To go along with the third wave of feminism, the '90s were all about the pantsuit. So Diana traded her skirt suits of the '80s for this chic, oversized gray suit. We love the fringe detail on the lapel. The princess put this on to have lunch with her stepmom, and in a power suit like this, it must have been a power lunch.
Baby Pink
It's not that the '90s didn't have any color, but the colors that were used were either muted or pastel compared to the bright neons of the '80s. This baby pink suit was designed by Versace and makes Diana look like a sophisticated Barbie. She sported it while in Argentina in 1995. It was actually a piece she wore more than once throughout the '90s, so it must have been one of her favorites.
Baby Blue
Another popular pastel color in the '90s was baby blue. The princess wore this crystal embellished Jacques Azagury dress to the ballet in 1997 — just a couple of months before her death. By now, she had divorced Prince Charles and was taking even more fashion risks, like wearing this rather low-cut dress.
Striped Sweater
We saw the princess in baby pink and baby blue, now see her in a combo of the two. This sweater hit all the '90s trends. It was oversized, striped, and pastel-colored. She paired it with white jeans and blue flats on her way to go play tennis in the spring of 1997. We wish she could have lived longer so we could have seen her other decades of fashion. Diana in the early 2000s would have been iconic.
