Princess Diana’s 20 Most Iconic Hat Moments

by Karen

Princess Diana was famous for many things - from her volunteer work to her natural beauty. Her legacy also lives on through fashion. This legendary royal had a way of always looking chic no matter the occasion. Her clothing was stunning and so were her accessories.

To pay tribute to her iconic sense of style, here are Princess Diana’s 20 Most Iconic Hat Moments.


Lady In Red

This charming red hat from designer John Boyd was worn during a visit to Halifax, Nova Scotia in 1983. She paired it with a red and white checkerboard print dress.

Princess Diana Lady in Red

Barely Veiled

Lady Di was known for her captivating gaze. On a trip to Canada in 1983, she wore a breathtaking baby blue hat accented by a bow and a lovely birdcage veil.

Princess Diana Barely Veiled

Looking Luxe

Dressed in ivory from head to toe on a trip to Tasmania in 1983, this statement-making fascinator paired a petite veil with a lovely floral accent on the side.

Princess Diana Looking Luxe


Pretty In Pink

Princess Diana always looked incredibly ladylike. But on a trip to the Sydney Opera House in 1983, she embraced her femininity by styling a floral dress with a pink hat. A strand of pearls tied the entire look together.

Princess Diana in Pink

Retro-Inspired Glamour

This pillbox hat was a charming reference to the 1960s. She wore this statement accessory to a charity event in 1983.  

Princess Diana Retro-Inspired Glamour

 Elegant & Artistic

This fashion-forward hat from Frederick Fox was perfect for her trip to Anzio, Italy in 1985.  The bold shape is softened by the white brim.

Princess Diana elegant and Artistic

Sailor Chic

Princess Diana wore a chic version of a sailors hat while aboard a boat in La Spezia, Italy in 1985. On anyone else this might have looked silly, but Diana makes it work thanks to her sharp pinstripe suit.

Princess Diana Sailor Style

Elegant Yet Extravagant

This entire ensemble - which she wore to Easter services in 1987 - perfectly showcases the excess nature of late 80s fashion. This pale blue hat features an oversized brim and is complemented by a white belt.

Princess Diana Elegant Yet Extravagant



When visiting the always fashionable  city of Paris in 1988, Diana paired an all-black outfit with a bold top hat from designer Viv Knowlands. The red poppy on her lapel adds a perfect pop of color.

Princess Diana Prim Parisienne


1920s Inspired

Princess Di took a cue from the 1920s when she adorned her look with an ivory cloche hat in 1991. This beautiful, minimalist accessory was designed by Philip Somerville.

Princess Diana 1920s inspired


Over The Top

There are dramatic accessories…and then there is this oversized hat from Philip Somerville. Princess Diana wore this lavender and black net hat to an event at Green Park, London in 1994.

princess Diana over the top hat


Bold Color Blocking

It’s impossible to ignore the bold, structured top hat Princess Diana wore in 1995. The white and navy color blocking gives it a slightly nautical appearance - especially when paired with a button-down dress.

Princess Diana Bold Color Blocking


Regal Royalty

Although feminine, this regal ensemble worn by the princess in 1982 would be nothing without the sharp, military-inspired Glengarry-style hat.

Princess Diana Regal Royalty


Sweet & Sophisticated 

Usually, Princess Di’s hats would match the color of her dress. On a visit to New Zealand in 1983, she wore a green dress and white accessories - including this sweet bowler hat.

Princess Diana Sweet & Sophisticated

Garden Party Ready

Floral ribbons accented this lovely, vintage-inspired hat that Princess Diana wore in 1983.

Princess Diana Garden Party

Victorian Era

Princess Diana channeled a bygone era when she wore this wine-colored hat from designer John Boyd. The matching dress made it the definition of old fashioned elegance.

Princess Diana Victorian era hat


Beret Beautiful

Not everyone can pull off a red beret…but not everyone is Lady Diana. Her red and black outfit is stunning thanks to the bold beret, which she wore to a ceremony in 1984

Princess Diana Beret Beautiful

Middle Eastern Glam

On a trip to Dubai in 1989, she wore a turban-style hat by designer Philip Somerville. The bold colors and matching lapels make it even more eye-catching.

Princess Diana Middle Eastern Glam


Prints on Prints

This look proves that the beautiful Princess Diana could pull off anything. On a lesser woman, this all-tartan outfit would have been too much. But she manages to make it look truly inspired. 

Princess Diana Prints on Prints


First Lady Inspired

The royal channeled the equally iconic Jackie O when she wore this pink pillbox hat in 1995. A matching Versace dress made her entire look even more presidential.

Princess Diana First Lady Inspired

Want Some Of Her Style For Yourself?

Our collection of vintage-inspired hats allows you to have your own iconic Princess Diana moment. Here are our top picks, all inspired by The People’s Princess.


Pair this with a pastel-colored dress and pearls for a head to toe look that is fresh, feminine, and sophisticated.


Go bold by pairing this black fascinator with a black dress. Add a bright shoe or a bold handbag to add a stunning pop of color.


This stylish hat has an over-the-top personality, which mimics some of Princess Diana’s early looks. Wear it with a burgundy dress to feel like royalty.




Princess Diana hats infographic

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