Princess Diana's 50 most iconic fashion moments

1

1981

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.

2

1981

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.

3

1981

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

4

1981

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

5

1981

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.

6

1982

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.

7

1983

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.

8

1985

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

9

1985

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

10

1985

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.

11

1985

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

12

1985

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

13

1986

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

14

1986

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

15

1987

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.

16

1987

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

17

1988

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

18

1988

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

19

1988

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

20

1988

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

21

1988

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

22

1988

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 Even wearing a trend that now feels so outdated, Diana manages to still seem timeless.

23

1989

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

24

1989

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.

25

1989

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

26

1989

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.

27

1989

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).

28

1989

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

29

1989

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

30

1989

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

31

1989

Color blocking at its finest, this suit and hat certainly left an impression.

32

1990

As she entered the nineties, Diana set the trend for the decade's minimalistic style.

33

1990

Most people today wouldn't dare wear a dress, shoes, and clutch all in the same bright red color, but Diana pulled it off impressively. She apparently rewore this dress eight separate times.

34

(1992)

This dress was actually a repurposed version of another gown Diana worn before, showing the world that even a Princess can recycle her clothes.

35

1992

OK, in all fairness, this outfit isn't nearly as legendary as the famous photo it produced, but the red jacket and purple skirt combo still deserves a mention.

36

1994

Ah, yes, the "revenge" dress. Diana famously wore this LBD the day Prince Charles publicly admitted to having an affair. Needless to say, she knocked him off the front page the next day.

37

1995

Post-separation from Prince Charles, Princess Diana didn't shy away from showing a little leg, like in this white Versace number.

38

1995

Sometimes simple is better, as Diana proved with this statement blue coat worn over a plain black dress.

39

1995

Before crop tops and two-piece sets were cool, Diana wore a dress that gave the illusion of both.

40

1995

That neckline! This Catherine Walker dress was daring but still totally tasteful.

41

1995

What do you wear to present at the CFDA Awards? A navy blue dress with a new slicked-back hairstyle.

42

1996

For Princess Diana's one and only visit to Chicago, she wowed by accidentally wearing "Northwestern Purple."

43

1996

This Versace dress that Diana wore on her tour of Australia fit her like a glove, and cemented this blue as a trending color.

44

1996

Wait, is that lace I see? Diana wore a hint of the lingerie-esque trend that took over the '90s (and has made a resurgence in the past few years).

45

1997

While visiting patients in a hospital in Angola, Diana sported a classic chambray shirt and chinos.

46

(1997)

Yes, the front of this dress is beautiful, but what really made it stand out was the lace insert in the back, which you can see in this video.

47

1997

This Catherine Walker dress screamed "legs for days."

48

1997

It takes a special type of person to wear a red this vibrant, and this gown was fitting for the American Red Cross Gala Diana was attending.

49

1997

When you meet Mother Teresa, wearing white seems like the appropriate choice.

50

1997

Princess Diana wore this blue dress to the ballet Swan Lake. It's hard to stand out amongst a sea of beautiful ballerinas, but she obviously did. And, FYI, her necklace was just put on sale for $12 million.

Princess Diana's 50 most iconic fashion moments

In honor of what would be her 56th birthday, a look back at her best outfits.

1981

1981

1981

1981

1981

1982

1983

1985

1985

1985

1985

1985

1986

1986

1987

1987

1988

1988

1988

1988

1988

1988

1989

1989

1989

1989

1989

1989

1989

1989

1989

1990

1990

(1992)

1992

1994

1995

1995

1995

1995

1995

1996

1996

1996

1997

(1997)

1997

1997

1997

1997