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From March 10 to 13, Cheltenham transforms into a bustling hub as hundreds of thousands gather for an event akin to a winter Royal Ascot or the countryside’s answer to London Fashion Week—the Cheltenham Festival.

While the thrill of the races is undeniable—with prize money for the main event second only to the Grand National—this year, fashion takes the spotlight more than ever before.

Why is that? Ladies Day, a tradition steeped in history, makes a grand return following its 2019 hiatus, offering £10,000 in prizes for the best-dressed attendees.

This promises to be a true ‘country catwalk,’ featuring the elite of high society, including numerous royals, parading the finest in British fashion. What makes it even more exciting is that the styles showcased often set the stage for future trends in rural chic. Their enduring appeal and quality offer valuable inspiration to everyone, city dwellers included.

It promises to be a true ‘country catwalk’, with the good and great of the country’s smartest social circles, including royals a-plenty, out showcasing the very best of British fashion. And the best bit? The outfits on show at Cheltenham often forecast upcoming trends in rural vogue, from whose timeless aesthetic and made-to-last quality there’s something we can all learn – even city dwellers. 

Here are the five brands the racing set will be wearing, plus how to incorporate the right amount of country chic into your own wardrobe…

Dubarry is to country dwellers what butter is to a hot crumpet – essential and inseparable and the brand has had a presence at Cheltenham for the last 25 years

Dubarry is to country dwellers what butter is to a hot crumpet – essential and inseparable. One cannot exist without the other. The boot rooms of country piles are littered with decades-old pairs of the brand’s iconic boots, passed between generations. And Dubarry takes the biscuit for Cheltenham longevity – the brand has had a presence at the Festival for 25 years and boasts a store in the town, too. 

Cheltenham veteran Georgia Toffolo has been spotted in the more fashion-forward black version of their signature Galway boots (£379, dubarry.com), while the Princess of Wales is a long-time fan, stepping out just last month for a walk in the Peak District in a Dubarry jacket. The ultimate racing-inspired Dubarry bargain? Their Sweetalison tie neck blouse, whose stallion print nods to the equestriancore trend set to dominate this AW, is now £59 in the sale. 2026 is year of the horse, after all.

Heritage tailoring and British craftmanship are at the forefront of Holland Cooper, but this tradition is uniquely fused with modern design

The announcement of Holland Cooper as the Official Luxury Fashion Partner of the Jockey Club was a full-circle moment for the brand, whose founder Jade Holland Cooper first exhibited in the Cheltenham Festival shopping village in 2008. 

Now, the brand boasts a brand-new, custom-built 70,000 sqft HQ in Cheltenham, while their stand at the Festival is the perfect place to celebrity spot – last year, society darlings Plum Sykes and Jodie Kidd and none other than Mary Berry were amongst the bevvy of VIPs in the brand. Heritage tailoring and British craftmanship are at the forefront of Holland Cooper, but this tradition is uniquely fused with modern design. 

And that’s where Holland Cooper has triumphed: they’ve single-handedly breathed new life into the once-stuffy landscape of country fashion through fusing its classic techniques with more expressive, bolder silhouettes and textures, meaning their clothes boast a versatility that befits a boardroom as much as a grouse moor. Their new circle skirt (£599, hollandcooper.com) embodies this fusion, reimagining tweed in a vivid red check.

Fairfax & Favor began in 2012 and thirteen years on, the brand’s fan club has expanded to include Zara Tindall and Lady Alice Manners

Fairfax & Favor began in 2012 with a single idea: a beautifully made women’s boot that united style and practicality. Thirteen years on, that boot – the iconic Regina now synonymous with Cheltenham – has sold over 150,000 pairs globally, generating more than £36million in sales. 

The brand’s fan club – a veritable who’s who of racing – is testament to the ability of their block heels to withstand Cheltenham’s notoriously treacherous underfoot conditions. Zara Tindall, arguably the Queen of Cheltenham style, is their Official Brand Ambassador. Likewise, Lady Alice Manners, a regular of racing’s best-dressed lists, has recently collaborated with the brand on a photoshoot, shot at her family home of Belvoir Castle. 

The leather Upton boots (£445, fairfaxandfavor.com) will work just as well over jeans in the city as at a racecourse, while ITV Racing presenter Francesca Cumani loves their top-handled Loxley bag (£295) – perfect for practical style at all types of winter events.

Schöffel combines the brand’s roots in technical skiwear with style, creating outerwear that is incomparably functional

It is a truth universally acknowledged amongst real racing veterans that Cheltenham racecourse operates as a micro-climate whose temperature is inexplicably yet unfailingly at least 10 degrees colder than outside its gates. 

The solution? Schöffel. Because of the brand’s roots in technical skiwear, their outerwear is incomparably functional. Having comfortably skied in -30 degrees in Schöffel’s ski coats, British country enthusiast Corry Cavell-Taylor saw an opportunity in the ’90s to transfer the technology of the originally Bavarian brand’s skiwear to British outerwear. This commitment to performance still informs their product offering today, but – crucially – is united with style. 

Their Portree coat (£450, schoffelcountry.com) is just as good at combatting the chill while you wait for the tube as it is Cheltenham’s icy winds.

Tweed – Cheltenham Festival’s unofficial uniform – is what Cordings does best and it’;s not just for the racing crowd with Claudia Winkleman among their fans

Even rockstars love the country look. Eric Clapton was such a longtime fan of Cordings’s tweed jackets that he acquired a stake in the brand in 2003 (joking he stepped in to help preserve the brand only so he could continue shopping there). And, as Eric knows, tweed – Cheltenham Festival’s unofficial uniform – is what Cordings does best. 

Step foot in their wonderfully old-world-y shop in Piccadilly and, as well as British aristos a-plenty, you’ll find the changing rooms full of the chicest Europeans trying on tweed jackets to wear with jeans on the streets of the continent’s capitals. 

Claudia Winkleman likewise paired their Wetherby tweed waistcoat (£202, cordings.co.uk) with a pair of Reiss tailored trousers on The Traitors recently. Proof tweed isn’t just for the racing crowd.