Princess Diana’s 50 Most Iconic Fashion Moments

In her engagement photos, a fresh-faced Lady Diana Spencer wore sapphire blue to match her engagement ring, and the photos were an instant hit.

No one wears wellies like Princess Di wore wellies. Although not one of her most famous looks, this outfit from before her wedding inspired women across the world to haul out their rainboots.

Diana’s wedding gown, in all its 1980s glory, was instantly iconic after her nuptials aired to an estimated TV audience of 750 million.

In phase one of the Diana and Charles honeymoon, this dress made waves. Who says florals have to be boring?

When your honeymoon includes hunting and fishing at a Scottish estate, it’s best to try to do it in style, like in this two-piece tweed set.

If this dress that Diana wore during her first pregnancy looks familiar, it may be because Kate Middleton wore a very similar outfit when she left the hospital with Prince George.

A princess wearing pink doesn’t seem like anything revolutionary, but this outfit just further solidified Diana’s reputation as an icon. Many royals wear gloves at formal events, but Diana never did because she felt it made her closer to the people.

This Victorian-inspired gown became almost as famous as Diana’s dance partner in this photo, a young John Travolta.

For the royal family, wearing a bathing suit this skimpy is downright scandalous. For fashion fans around the world? Just right.

It’s hard to stand next to Nancy Reagan, one of the chicest first ladies in US history, and look this great. Diana pulls it off with ease in a white jacket and skirt.

Leave it to Princess Diana to take what was supposed to a choker and wear it as a headband.

In an outfit that was a little more on the conservative side, Diana seemed to be giving a nod to Jackie Kennedy.

Princess Diana had her daring style moments, but she knew how to be regal when the situation demanded.

Not one of her most memorable red carpet moments or anything, but who looks this good while skiing? Seriously.

This dress may seem simple, but it’s a classic formula: Cinderella style, baby blue. Princess Di wore it in Cannes. This dress sold at auction in 2011 for £80k.

Some say Princess Diana overdid it in this tartan Escada coat and Philip Somerville hat. In her defense, it was the ’80s!

Princess Diana attended the Remembrance Day ceremonies in a more somber look — but the birdcage veil still makes it stand out.

Only Princess Diana could wear cowboy boots, a sweatshirt, and a blazer in a totally unconventional but effortlessly cool ensemble.

Diana channels military-chic in this white and gold set.

Polka dots can often look overwhelming, but Princess Diana pulled them off in a stylish way.

Most people recognize this photo because of the always adorable Prince Harry, but Diana’s matching outfit was eye-catching, too.

Bring on the shoulder pads! Even wearing a trend that now feels so outdated, Diana manages to still seem timeless.

This photo could have been taken in 2017. Diana’s dress, hair, and makeup are totally classic. Is that millennial pink I see?

This sparkly column gown is another timeless Princess Di look. If you saw this on the red carpet in 2017, you wouldn’t bat an eye.

Diana had a knack for making casual look effortless and modern, which this tunic definitely does.

What’s the most luxurious thing in this picture, Diana’s dress, the Rolls Royce she’s climbing out of, or her tiara? The answer: all of the above.

The combo of this tiara, the high-collared jacket, and her signature blue eyeshadow had the press calling this Diana’s “Elvis” look (in a good way).

Compared to some of Diana’s other red carpet looks, this floral dress is almost tame, but still stunning nonetheless.

Note to self: Wear more hats. Diana’s matchy look was just bold enough to catch the world’s attention.

Another baby blue gown that instantly captured hearts when Diana wore it in Cameroon.