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The 10 most stylish Royal Ascot hats of all time

Still need headpiece inspiration for Royal Ascot 2023 next week? Look no further...

10 chicest Ascot Hats of all time : Meghan Markle, Hana Cross and Kate Middleton at Ascot
Lauren Ramsay
Online Writer
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Royal Ascot 2023 is just around the corner (or should we say, down the stretch). And like any other special occasion, meticulously planning an outfit is essential. But in some ways, the most fashion-forward event of the British social season requires that more work than the rest, because a headpiece is an integral part of the dress code.

Since the event began in 1911, Ascot fashion has always stuck to the sartorial rules that still stand today and haven't changed much overtime. Including the requirements around hats and fascinators. 

MORE: The 23 best Royal Ascot outfits of all time

RELATED: 5 Ascot 2023 outfit ideas that are actually pretty major 

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Particularly for those in the prestigious royal enclosure, the regulation is slightly more strict: "Hats must be worn. However, a headpiece or hatinator with a minimum base diameter of 4 inches/10cm is acceptable," is the advice on the official website.

Fear not though. This doesn't mean your inner fashionista has to compromise, as proven by the chicest slew of hats below. Throughout the festival's 112 year history, there has been some unforgettable headgear. And if you're still stuck on what to wear next week, use these stylish guests as inspiration...

The 10 best Royal Ascot hats of all time:

Princess Margaret, 1969

Princess Margaret at Ascot in 1969© Getty
Princess Margaret

For the fourth day of the races in 1969, Princess Margaret wore a dramatic white hat adorned with daisies.

Princess Diana, 1988

Princess Diana at Ascot in 1988© Getty
Princess Diana

The late of Princess of Wales wore a super chic black and white spotted dress by Victor Edelstein and a Philip Somerville hat.

A Guest, 1990

A Guest at Royal Ascot in 1990© Getty
A Guest

A guest took florals in summer and made it dramatic in the coolest poppy hat we've ever seen to grace Ascot.

Meghan Markle, 2018

The Duchess of Sussex at Ascot in 2018© Getty
The Duchess of Sussex

For the opening day of Ascot in 2018, Meghan oozed chic in a wide black-and white-hat by Philip Treacy. Meghan opted for a custom Givenchy dress made by creative director Clare Waight Keller.

Princess Kate, 2019

Princess Kate at Ascot 2019© Getty
Princess Kate

This look has become one of Princess Kate's most iconic in her tenure as British royal. Ascot 2019 is where she first wore this stunning powder blue Elie Saab dress and Phillip Treacy hat combo. Since then she has sported the exact same look this year, for the 2023 Buckingham Palace Garden Party.

Lady Kitty Spencer, 2019

Lady Kitty Spencer at Royal Ascot 2019© Getty
Lady Kitty Spencer

Princess Diana's niece wore this monochrome Phillp Treacy piece (noticing a royal millinery theme here?) in 2019. Rumour has it that she had to lie vertically in the car thanks to the OTT black spike sticking upwards. The kind of dramatic outfit we love.

Rosie Tapner, 2022

Rosie Tapner at Royal Ascot 2022© Getty
Rosie Tapner

Racing TV presenter Rosie Tapnerwore a totally royal-approved outfit, and a stunning hat. Both her chic lace dress and blue, grey and cream headpiece were created by Catherine Walker.

Princess Beatrice, 2022

Princess Beatrice of Yorkand Edoardo Mapelli Mozzi attend Royal Ascot 2022 at Ascot Racecourse on June 14, 2022© Getty
Princess Beatrice of Yorkand Edoardo Mapelli Mozzi

Beatrice oozed femininity in a Zimmermann dress and a floral headpiece by Juliette Botterill Millinery.

Betty Bachz, 2022

Betty Bachz at Royal Ascot in 2022© Getty
Betty Bachz

Betty stunned in a Preen by Thornton Bregazzi dress paired with the 'Mimi' boater boasting three origami crinoline birds from Awon Golding millinery.

Hana Cross, 2022

Hana Cross at Royal Ascot, 2022© Getty
Hana Cross

Hello! Fashion's December 2022 cover girl Hana Cross was the moment on Ladies Day last year in a rose-adorned dress by Alessandra Rich, paired with a black floral headpiece by Monique Lee millinery.

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