A sea of 10,000 baker boy hats bobs merrily through the gates at Prestbury Park. It’s a scene you could only take in at Cheltenham – Tuesday is day one of the festival, which feels particularly buoyant this year as racegoers are set to mark 100 years of the Cheltenham Gold Cup.

For those who are here for the haute outfits as much as the horses, it’s a chance to go all in. The look at this particular event is now as distinct as Royal Ascot. But while the Ascot audience swathes itself in pretty pastels, here it’s all about shades of brown. To fit in, you’ll want to wear heritage fabrics – tweeds and checks, dogtooth and herringbone – in hues to match the March mud.

Cheltenham is one big showcase of British country style – the regulars call it “rural Vogue”. There are attendees who have been coming for decades, who rewear the same tweeds annually making their own timeless style statement. There are others who see it as a chance to dress up, an occasion akin to planning your look for a family wedding. Many have spent weeks, if not months, preparing, often recruiting personal stylists such as Sarah Byrne and Annie Miall, who specialise in the genre.

“With the Gold Cup anniversary this year, it does feel particularly celebratory,” acknowledges Jade Holland Cooper, founder of the namesake country clothing label. “Cheltenham is a time for heritage style – it’s a beautiful, chic look. There’s an unspoken dress code [not officially set by The Jockey Club, like Ascot], but it’s now so known and understood.”

Holland Cooper knew months ago that on day one of this year’s event she would be wearing an emerald houndstooth set – an ankle-length skirt, paired with the matching coat.

“Moving the look forward whilst always retaining that timelessness is my goal each year,” she says. “We’re evolving classics. You could wear the same silhouette every day and update it with just the fabrics if you wanted to. The possibilities with traditional materials are endless – you can go wild in graphic pink dogtooth, or subtle in a black and white herringbone.”

For men, Holland Cooper’s ‘Cheltenham edit’ spans Prince of Wales check waistcoats and wool gilets, ‘tawny’ blazers with the matching caps. “It’s elegant classics, crossed with a bit of Peaky Blinders charm,” as she puts it.

Holland Cooper is one figure at the centre of the Cheltenham social set. The event gathers racing royalty (Rosie Tapner and Francesca Cumani) with actual royalty (Zara Tindall and Queen Camilla) to form an eclectic crowd. A coterie of country designers come with their muses, socialites from the city decamp to their country homes for a week of fun. 

As surely as celebrity culture in the Cotswolds has heightened in recent years, ‘outsider’ interest at nearby Cheltenham has too. The festival now attracts its share of fashion show ponies – those who are here for the dress up and the day out. And why not? Last year’s country style cosplayers included Matt Hancock and Carol Vorderman, as well as half the cast of Love Island. They all knew exactly what to wear – how could they not?

“Obviously the racing is top class, but it’s a massive social event as well,” says Francesca Cumani, the ITV Racing pundit. “There is no formal dress code at Cheltenham, but for me big race days always deserve a great outfit. I think it’s important to make an effort. The horses are always turned out immaculately, so we should be too.”

Cumani enjoys the fashion spectacle as much as anyone else – her own outfits in previous years have included a fuzz-trimmed grey houndstooth coat, and a neatly belted herringbone cape. 

“Zara Tindall never misses a day of the festival and always looks great,” she says of her tips on who to watch in the style stakes. “The stylist Sarah Byrne also looks fantastic – usually in something she has pulled together last minute after dressing everyone else.” 

For the Sky Sports Formula One presenter Natalie Pinkham and her husband Owain Walbyoff, Cheltenham offers a different style of race day – and a theme which they totally embrace. 

“It’s inked in the diary every year,” she confirms, “we always look forward to it. I’m used to following the sun in F1, so it’s a welcome change to enjoy a bit of winter chic.”

Pinkham cites Savile Row’s female tailor The Deck and The Huntsman as two brands she turns to for the occasion. “Milliners like Sarah Cant also offer such creativity to really make a look your own,” she adds.

Seeing people rewear and adapt old favourites makes for good sport. “Speaking to many ladies who go, I love that so much has been upcycled and adapted to create different looks,” she says. “These are bespoke pieces handed down through families and customised to suit their individuality.”

Injecting personality whilst dressing to a theme is a challenge that the men and women of Cheltenham take on wholeheartedly. A fabulous (and crucially warm) coat is the focal point of any outfit, but from there it’s the additions and accessories that can make a person stand out. The official best in (fashion) show this year will win a £4,000 Boodles necklace.

“Embracing creativity is key for racegoers, the addition of accessories adds vibrant pops of colour,” comments Alice Leet-Cook, co-founder of Hicks & Brown, the millinery brand loved by the Princess of Wales. The right headgear, she notes “can also keep the sun and rain out of your eyes whilst looking effortless.”

Many attendees travel in herds – couples coordination is a big deal in the stands.

“It’s a great opportunity to dress up – for me it’s about looking like I’m going to the races in a bygone era,” says Tom Joule, founder of Joules. He’ll wear a corduroy suit, to balance with his wife Alice, who’ll do the tweed. 

“With over 50,000 race goers a day, you want to stand out in the crowd,” adds Alice. “The theatre of Cheltenham makes you feel you want to play the part.”

Who’s who in the Cheltenham style set

Racing royalty

ITV racing presenters Rosie Tapner and Francesca Cumani bring some colour to proceedings. Horse owners Joe and Marie Donnelly are always impeccably turned out.

Real royalty

Zara and Mike Tindall never miss Cheltenham –  it’s just a short trot from Gatcombe Park. Queen Camilla attended last year wearing sandy suede boots and a fur trimmed hat. Princess Anne typically throws a colourful silk scarf over her brown and grey checks.

The rural vogue designers

Jade Holland Cooper (dressed head-to-toe in her own label) usually arrives with a celebrity friend on her arm –  last year it was Idris Elba. Mr and Mrs Joules, and stylists Sarah Byrne and Annie Miall also dress their part. It’s a sub-sport for Marcus Fairfax Fountine, co-founder at Fairfax & Favor, to spot how many in the crowd are wearing his brand’s signature Sienna cape.

The country-city commuters 

Another category of attendee is those who quite seamlessly and regularly blend from city to countryside; Georgia Toffolo, Natalie Pinkham, Luke Evans. Their wardrobes in their home (or homes) must hold sections for each lifestyle. 

Just horsing around 

They’re here for the day out. It’s Carol Vorderman, it’s Gareth Gates, it’s the cast of Love Island. But they’ve certainly nailed the dress code, in tweed and checks. 

Get the Cheltenham look…

Suffolk fedora, £99, Hicks & Brown; Newsboy cap, £69.95, Schoffel; Bloomfield silk scarf, £39.95, Joules

Gina suede top, £295, Fairfax & Favor; Single breasted blazer, £599, Holland Cooper