Moms and Dads

25 of Princess Diana’s Most Iconic and Timeless Looks

by Kevyn Gohu
September 2, 2022

Celebrate the 25th Death Anniversary of Princess Diana with her most iconic and timeless looks!

Remembered as the “People’s Princess”, Princess Diana’s death shook the world. Although her marriage with Prince Charles was nothing short of turbulent, it didn’t stop her from being a wonderful mother to Harry and William. To many, she will always be the Princess of Wales. And to remember her on her 25th death anniversary, here are 25 of Princess Diana’s most iconic looks that will still make waves in today’s fashion.

1. Princess Diana’s Wedding Gown

Princess Diana’s Wedding Gown was considered one of the most well-guarded secrets of the fashion industry. It sported a 25-foot-long train, made of ivory taffeta and antique lace. Princess Diana personally chose David and Elizabeth Emanuel as the designers because she loved the chiffon blouse they made.

The wedding gown, in 2018, was considered the “Most Influential British Royal Wedding Dresses of All Time” because hours later, brides-to-be made requests to designers to “replicate” it.

2. The Revenge Dress

When Camille and Prince Charles’ relationship went public, Princess Diana sported her iconic “little black dress” look. Designed by Christina Stambolian, the dress was considered “daring” during her time and she wore it on the day Charles revealed his cheating — hence its title. She sported it in 1994 during her appearance in the Serpentine Gallery.

3. Downtime Diana

Many remember Princess Diana for her multiple royal engagements. But the late princess had her downtime too, sporting an oversized black jacket with a casual white t-shirt, faded jeans, and tan leather boots. She even made a baseball cap look chic!

4. Casual Blazer and Sneakers

Ever wonder when and how blazers and sneakers became a thing? While there’s no exact origin, Princess Diana knew how to make this iconic look work. She coordinated her blazer and walking sneakers to be navy blue to match her all-denim inners.

5. Neutral Co-ords

With neutral being all the rage now, take a page out of Princess Diana’s book as she casually went around in a beige-colored suit co-ord with a white inner. It’s also in this photo that many said it was one of her last “smiling photos” with her son, William, as they were on their way to lunch in Chelsea.

6. A Jumpsuit and Pink Converse

Royal or not, everyone needs a pair of Converse sneakers. Princess Diana had a cute pale pink pair for herself!

7. The “Elvis” Dress

Pearls will always be a classic and this pearl-adorned white dress and bolero set was designed by one of Princess Diana’s preferred designers, Catherine Walker. She wore the dress in October 1989 during fashion week in Hong Kong. Quoted by InStyle in 2012, Catherine Walker revealed how she “couldn’t imagine anyone else [sans Princess Diana] wearing the iconic look”.

8. The Polo and Jeans look

Admit it, as moms, some just throw on a polo and jeans for an instant simple and chic look. It just so happens Princess Diana thought the same.

9. The Yellow Sundress

Along with her inspiring and illuminating smile, the late Princess Diana sported a yellow high-neck sundress while visiting school kids in Australia. She also paired them with white leather accessories.

10. Going All White

Some are afraid to wear all white but Princess Diana does it right. With a black belt, a black and white pair of flats, and a large floral tote for accent, she struts a more casual look with a white tank top and jeans.

11. Princess Diana’s Athleisure Look

She was doing athleisure before it became cool. This iconic Princess Diana athleisure look involved a large sweater, a pair of cycling shorts, calf-high socks, and a pair of sneakers.

12. The Black Sheep Sweater

Princess Diana was not one to shy away from repeating the same outfit twice. But her Black Sheep look became iconic because it sent a loud message when she became a royal. As if telling the world that she was still “an outsider”. Prince Harry even replicated this look once!

13. Elephant Suit and Tie

Suits and ties are often for men but Princess Diana sported hers quite well. She wore a navy blue suit with golden elephants as a pattern on her tie and cuff links.

14. The Princess Biker Look

Nobody said that a princess can’t wear a black leather jacket. The black leather jacket has always been a classic that even Princess Diana made it work with a red t-shirt, jeans, and white rubber shoes.

15. Ice Blue Satin Dress

Being pregnant did not exempt Princess Diana from her royal duties. While pregnant with Prince Harry, she looked absolutely glowing in an ice blue satin dress with a drop-waist silhouette.

16. White Suit with a Black Bow Tie

Princess Diana looked absolutely dapper with her white suit combination and her little black bowtie. She also used a black clutch to serve as an accent with her suit.

17. The Nautical Look with a White Pleated Midi Skirt

The late princess of Wales was certainly fond of her pleated midi skirts. She once wore a white pleated midi skirt with a nautical-themed sweater to match her metallic flats.

18. White and Black Puff Sleeves

A mom’s greatest frustration, if not her belly, is her arms being flabby. Princess Diana’s puff-sleeved look is perfect for moms who wish to hide their arms but still look chic.

19. Polka Dot Dress

Nothing screams Happy New Year or luck more than a polka dot dress. Some even say that wearing polka dots means ushering more money for the year. If not a top, try a polka dot dress like Princess Diana’s.

20. Pinstripe Suit or Pants

Pinstripes were one of Princess Diana’s more frequented patterns besides Tartan for her visits to Scotland. The pattern still works, creating a rather slimming and elongated silhouette.

21. Culottes or Capri Pants

Culottes or Capri Pants are making a comeback and go pretty well with a white polo. Princess Diana sported a pair of capri pants with a white polo and a red cardigan draping on her shoulders. She also used some bright-colored heels to make the look work, too.

22. Black Gowns

When it comes to formal events save for weddings, one can’t go wrong with a black gown. Princess Diana often favored the off-shoulder neckline for her gowns or dresses.

23. Her Little White Dress

There’s nothing wrong with having a little white dress. Black might rub people the wrong way so having a little white dress helps. Princess Diana also had one to match with her silver clutch since not many were too fond of her wearing black.

24. Turtle Neck

Turtlenecks can be both casual or formal, depending on the bottom and shoes. Princess Diana sported a bright red one but not without pairing it with a thick cinch belt, a black and white checkered skirt, and a pair of black heels to elevate the outfit.

25. Suit Dress

Possibly one of the most flexible attires, Princess Diana always had a suit dress for her royal engagements. Considering how they could be both smart casual or formal, it’s no surprise she had a whole lot of them.

Princess Diana was iconic not just in fashion but as a mother and a princess.

Until today, many mourn her death. A beloved icon, she created so many ripples in the world that many of her beneficiaries and family members still feel it. Princess Diana is a woman who still inspires even beyond the grave, setting up the standard and stage for those who wish to attain a certain level of grace, poise, and benevolence akin to royalty.