A sea of 10,000 baker’s boy hats float happily through the gates of Prestbury Park. It’s a scene you can only admire in Cheltenham – Tuesday is the first day of the festival, which feels particularly lively this year as racegoers celebrate the 100th anniversary of the Cheltenham Gold Cup.
For those who are here for the haute outfits as much as the horses, this is a chance to go all in. The view of this particular event is now as different as that of Royal Ascot. But while the Ascot crowd dons beautiful pastel colours, here it’s all about shades of brown. To fit in, you’ll want to wear classic fabrics – tweeds and checks, dogtooth and herringbone – in shades that match the March mud.
Cheltenham is one big showcase of British country style – the regulars call it ‘country Vogue’. There are participants who have been coming for decades and who wear the same tweed every year, making their own timeless style statement. There are others who see it as an opportunity to dress up, an occasion akin to planning your look for a family wedding. Many have spent weeks, if not months, preparing and often recruiting personal stylists like Sarah Byrne and Annie Miall, who specialize in the genre.
“With the Gold Cup anniversary this year, it feels particularly festive,” acknowledges Jade Holland Cooper, founder of the country clothing label of the same name. “Cheltenham is a time for heritage style – it’s a beautiful, chic look. There is an unspoken dress code [not officially set by The Jockey Club, like Ascot]but it is so well known and understood now.”
Holland Cooper knew months ago that she would wear an emerald green houndstooth set on the first day of this year’s event: an ankle-length skirt, paired with the matching coat.
“Taking the look forward while maintaining that timelessness is my goal every year,” she says. “We evolve classics. You could wear the same silhouette every day and update it with just the fabrics if you want. 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’ consists of checked waistcoats and wool waistcoats with Prince of Wales motif, and ‘tawny’ blazers with matching caps. “They are elegant classics, crossed with a bit of Peaky Blinders charm,” as she puts it.
Holland Cooper is a figure at the center of Cheltenham’s social atmosphere. The event brings together racing royalty (Rosie Tapner and Francesca Cumani) with real-life royalty (Zara Tindall and Queen Camilla) to form an eclectic crowd. A group of rural designers come to their country homes with their muses, city socialites, for a week of fun.
Just as celebrity culture has increased in the Cotswolds in recent years, so has ‘outsider’ interest in nearby Cheltenham. The festival now attracts its fair share of fashion show ponies, those who are here for the fancy dress parties 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?
“The racing is obviously top class, but it is also a hugely social event,” said ITV Racing expert Francesca Cumani. “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 immaculate outside, so we have to be too.”
Cumani enjoys the fashion spectacle as much as anyone else; her own outfits in recent years have included a gray houndstooth coat with fluff trim and a herringbone cape with a neat belt.
“Zara Tindall never misses a festival day and always looks great,” she says of her tips on who to keep an eye on when it comes to style. “The stylist Sarah Byrne looks fantastic too – usually in something she threw together at the last minute after dressing everyone else.”
For Sky Sports Formula 1 presenter Natalie Pinkham and her husband Owain Walbyoff, Cheltenham offers a different style of race day – and a theme they fully embrace.
“It’s on the agenda 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 names Savile Row’s female tailor The Deck and The Huntsman as two brands she will turn to for the occasion. “Modists like Sarah Cant also offer so much creativity to really make your look your own,” she adds.
Seeing people renew and adapt old favorites is good sport. “When I talk to a lot of ladies who go, I love that so much has been upcycled and modified to create different looks,” she says. “These are custom pieces passed down through families and adapted to their individuality.”
Injecting personality while dressing to a theme is a challenge that the men and women of Cheltenham take on wholeheartedly. A fantastic (and crucially warm) coat is the focal point of any outfit, but from there it’s the additions and accessories that can make someone stand out. This year’s official ‘best in (fashion)’ show wins a £4,000 Boodles necklace.
“Embracing creativity is essential for racegoers, the addition of accessories adds vibrant pops of colour,” says Alice Leet-Cook, co-founder of Hicks & Brown, the hat brand loved by the Princess of Wales. The right headgear, she notes, “can also keep the sun and rain out of your eyes while making you look effortless.”
Many visitors travel in herds – coordination of couples is a major problem in the stands.
“It’s a great opportunity to dress up – for me it’s about looking like I’m going to the races of a bygone era,” says Tom Joule, founder of Joules. He will wear a corduroy suit, to counterbalance his wife Alice, who will do the tweed.
“With more than 50,000 racegoers a day, you want to stand out from the crowd,” Alice adds. “The Cheltenham theater makes you feel like 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 color to proceedings. Horse owners Joe and Marie Donnelly are always impeccable.
Real royalty
Zara and Mike Tindall never miss Cheltenham – it’s just a short trot from Gatcombe Park. Queen Camilla attended last year in sand-colored suede boots and a fur-trimmed hat. Princess Anne usually throws a colorful silk scarf over her brown and gray checks.
The national fashion designers
Jade Holland Cooper (dressed from head to toe in her own label) usually arrives with a famous friend on her arm – last year it was Idris Elba. Mr and Mrs Joules, and stylists Sarah Byrne and Annie Miall also dress their parts. It’s a subsport for Marcus Fairfax Fountine, co-founder of Fairfax & Favor, to see how many people in the crowd are wearing his brand’s signature Sienna cape.
The commuters from the country to the city
Another category of visitors are those who move from city to countryside quite seamlessly and regularly; Georgia Toffolo, Natalie Pinkham, Luke Evans. Their wardrobes in their home (or homes) should contain sections for every lifestyle.
Just running around
They are here for a day out. It’s Carol Vorderman, it’s Gareth Gates, it’s the cast of Love Island. But they certainly stuck to the dress code, in tweed and checks.
Go for the Cheltenham look…
Suffolk fedora, £99, Hicks & Brown; Newsboy Cap, £69.95, Hoe
Gina suede top, £295, Fairfax & Gunst; Single breasted blazer, £599, Holland Kuiper
Bloomfield silk scarf, £39.95, Joule