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10 chicest Ascot Hats of all time : Meghan Markle, Hana Cross and Kate Middleton at Ascot

The 20 most stylish Royal Ascot hats of all time

Need headpiece inspiration for weddings or race days? Look no further...

Lauren Ramsay
Fashion and Lifestyle Writer
Updated: June 24, 2024
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Like any other special occasion, meticulously planning an outfit is essential. But in some ways Royal Ascot, 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. 

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 from 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, scroll on to use these stylish guests as inspiration...

MORE: The History of Ascot Fashion from 1711 - 2024

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

What hats can I wear at Ascot?

Royal Enclosure: In Ascot's Royal Enclosure, it is a requirement that all guests wear hats. The tradition and formality of the event calls for stylish and elegant headwear. Acceptable hats include wide-brimmed styles, and hatinators. A hatinator, similar to a fascinator but generally larger, should have a minimum base diameter of 10cm to meet the dress code. "A headpiece or hatinator with a minimum base diameter of 4 inches / 10cm is acceptable," the official dress code stipulates. This rule ensures that the headpiece is substantial enough to maintain the event's sophisticated aesthetic. So, whether you choose a classic hat, a chic fascinator, or a stylish hatinator, make sure it meets the size requirement to enjoy the day in compliance with Ascot's dress standards.

ASCOT, ENGLAND - JUNE 20: Hana Cross attends day one of Royal Ascot 2023 at Ascot Racecourse on June 20, 2023 in Ascot, England. (Photo by Kirstin Sinclair/Getty Images for Royal Ascot)© Kirstin Sinclair
Royal Ascot's formal dress code means we a treated a plethora of stunning hats

Queen Anne Enclosure and Village Enclosure: The rules here still require a headpiece, but it is slightly more relaxed than in the Royal Enclosure. "A hat, headpiece or fascinator" are all deemed acceptable by Ascot's guidelines. 

Windsor Enclosure: While there is no official dress code for the Windsor Enclosure at Ascot, guests are encouraged to dress in smart daywear to match the event's elegant atmosphere. "A hat, headpiece or fascinator is encouraged," explains the guide. Embracing these accessories not only enhances your outfit but also allows you to fully participate in the festive and stylish spirit of Ascot.

What hats can I not wear to Royal Ascot?

Fascinators are a big no-no in the Royal Enclosure. A fascinator is a small, decorative headpiece attached to a band or clip, often adorned with feathers, flowers, or beads, but they are often not formal enough to meet the strict dress code. 

The 20 best Royal Ascot hats of all time:

1/20

Eugenie is an artistic director© Max Mumby/Indigo

Princess Eugenie - 2024

Princess Eugenie accessorised her Ascot look with an Emily London pink boater featuring a decorative bow, and tasseled hat pin, which added a touch of playful elegance.

2/20

Harriet wore a splendid hat© Max Mumby/Indigo

Harriet Sperling

This delicate cream ecru straw teardrop beret percher was a stunning choice from Harriet Sperling. Trimmed with a twisted straw bow and featuring a large, dramatic flower made from soft, flowing fabric. The structured base of the hat provided a perfect balance to the oversized floral detail, creating a harmonious and eye-catching look.

3/20

Laura-Ann Barr© Chris Jackson

Laura-Ann Barr - 2024

Little Buds founder Laura-Ann Barr brought Barbiecore to the racecourse in a vibrant pink headpiece, with rose accents, that added a romantic touch to the day.

4/20

Louise Roe - 2023© Kirstin Sinclair

Louise Roe - 2023

TV presenter and style icon Louise Roe attended day four of Royal Ascot in a stunning daisy adorned netted beret. 

5/20

Hana Cross at Royal Ascot, 2022

Hana Cross - 2022

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.

6/20

Princess Kate Middleton on June 17, 2022 in Ascot, England. (Photo by Chris Jackson/Getty Images)© Chris Jackson

Princess Kate - 2022

Princess Kate's sophisticated wide-brimmed hat was a classic. The hat combined a chocolate base with white floral accents along the brim, creating a striking contrast.

7/20

Betty Bachz at Royal Ascot in 2022

Betty Bachz - 2022

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

8/20

Princess Beatrice wearing a floral headpiece at Royal Ascot at Ascot Racecourse on June 14, 2022 © Getty

Princess Beatrice - 2022

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

9/20

Rosie Tapner at Royal Ascot 2022

Rosie Tapner - 2022

Racing TV presenter Rosie Tapner wore 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.

10/20

Hum Fleming - 2021© Kirstin Sinclair

Hum Fleming - 2021

British fashion insider Hum Fleming wore a menswear-inspired headpiece designed to emmulate a classic top hat during Royal Ascot 2021.

11/20

 Emma Weymouth, Marchioness of Bath attends day 3 of Royal Ascot at Ascot Racecourse on June 17, 2021 in Ascot, England.© Max Mumby/Indigo

Emma Thynn, Marchioness of Bath - 2021

Emma Thynn's unique hat was a pale pink creation featuring an abstract, sculptural form. The hat includes intricate, folded fabric details that create a sense of movement and texture, complemented by the delicate pink hue.

12/20

Lady Kitty Spencer at Royal Ascot 2019

Lady Kitty Spencer - 2019

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.

13/20

Princess Kate at Ascot 2019

Princess Kate - 2019

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 sported the exact same look for the 2023 Buckingham Palace Garden Party.

14/20

Harry and Meghan attended Royal Ascot shortly after their wedding© Getty

The Duchess of Sussex - 2018

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.

15/20

Viscountess Serena Linley - 1994© Tim Graham

Viscountess Serena Linley - 1994

The future Countess of Snowdon, who married David Armstrong-Jones, the only son of Princess Margaret, dazzled in a oversized lilac hat covered in purple plumage. 

16/20

A female racegoer wearing a black dress, black evening gloves, and a red poppy hat on the first day of the Royal Ascot, 19 June 1990.© Tim Graham

Flower Power - 1990

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

17/20

Diana, Princess of Wales attended Ascot race meeting in England, wearing a black and white spotted dress by Victor Edelstein and a Philip Somerville hat, June 1988.  © Princess Diana Archive

Princess Diana - 1988

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

18/20

Princess Margaret (1930 - 2002) and the Queen Mother (1900 - 2002) arriving for the fourth day at Ascot© George W. Hales

Princess Margaret - 1969

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

19/20

Mrs. James Elliott - 1965© Mirrorpix

Mrs. James Elliott - 1965

The racegoer stunned in a large hat crafted from French lace and net. More is more. 

20/20

Yvonne Bentley - 1964© Fox Photos

Yvonne Bentley - 1964

Yvonne protected her tall hat from the rain on Ladies Day at Ascot racecourse. The hat, which she made herself, was 18 inches high and made of white nylon.

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