The best Cheltenham Festival outfits of all time

Publish date: 2024-04-20

See the most incredible fashion moments from throughout the races history...

Cheltenham festival is one of the most illustrious events in the British social season calendar.

Racegoers have been putting their best fashion feet forward since the race's beginnings in 1860, with everybody from royals to racing fanatics using the day to showcase their best outfits.

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Standout sartorial agendas have become an integral part of racing, particularly Cheltenham and Royal Ascot, with emphasis placed on elaborate dressing. Cheltenham is arguably the more relaxed of the two, considering it has no dress code, but instead suggests: "Style is as individual as you. The Cheltenham Festival is the perfect occasion to wear your best outfits and favourite accessories." 

This year, however, a major change was made to the racing roster. Ladies Day has been at the core of horse racing festivals for centuries - a day that traditionally encouraged women to dress to impress, but this year Cheltenham bosses announced they would be changing the name to 'Style Wednesday;' from 2024 onwards.

“This year we relaunched day two of the festival as Style Wednesday to celebrate ‘fast horses, slow fashion’, encouraging racegoers to make more sustainable fashion choices, showcasing their unique and personal style,” a statement said.

Opening the floor (or, track) to put more emphasis on style and less on gender, proves just how fundamental fashion is at the iconic races.

Here are some of the best Cheltenham Festival outfits of all time...

Jade Holland Cooper

The unofficial 'queen' of Cheltenham, as far as the style stakes are concerned, has to be eponymous designer Jade Holland Cooper. For the 2024 festival she was spotted arriving on day one in an utterly chic three-piece suit. 

Onyi Moss

Onyi Moss perfected Barbiecore chic in 2024, wearing a bubblegum pink mini dress and matching trench coat, paired with tights and black and gold block heels.

Pixie Lott

British singer Pixie Lott looked effortlessly glam in a checkered a-line jacket dress with a matching monochrome hat and a Holland Cooper crossbody bag in 2022.

Georgia Toffolo

Georgia Toffolo stole the show in 2022 when she wore the chicest Paul Costelloe dress paired with Givenchy boots.

Rosie Tapner

In 2022 Rosie Tapner was the epitome of country glam in a checkered coat suit, suede boots, silk scarf and fedora hat.

Liv Tyler

Liv Tyler perfected wearing all black at the races in 2017, wearing a long-sleeved midi dress, court pumps and a crocheted hat paired with an embellished handbag.

Princess Kate

Prince William's then-girlfriend Kate Middleton attended the final day of Cheltenham Festival on March 16, 2007 in a powder blue blazer and beret style fascinator. 

Sharron Davies

In 1999, Olympic Swimming champion Sharron Davies opted for a two-piece blazer and mini skirt set, paired with opaque tights and knee-high boots.

Princess Diana

In 1982, Princess Diana opted for a bold red mid-length coat paired with a red fascination and black ballet flats.

Lady Willoughby de Broke

In 1962, Rachel Verney, Lady Willoughby de Broke wore the chicest relaxed fitting jacket featuring 3/4 length sleeves and statement black details. She paired it with light-coloured arm-length gloves

Lady Mary Lygon

Lady Mary Lygon (right) wore a fluffy midi coat with a dramatic structured collar in 1937.

Diana Coventry

Miss Diana Coventry (left) wore a fluffy printed coat, strappy block heels and a black headpiece in 1931.

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