by A sea of 10,000 baker boy hats merrily rolls through the gates at Prestbury Park. It’s a sight you could only take in at Cheltenham – Tuesday is the first day of the festival, which this year feels like a big deal as racegoers get ready to celebrate 100 years of the Cheltenham Gold Cup.
For those who are here for the haute outfits as well as the horses, it is an opportunity to go all in. The look of this particular event is now as different 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 – tartan and checks, houndstooth and herringbone – in colors to match the March mud.
Cheltenham is one showcase of British country style – regulars call it “Country Vogue”. There are attendees who have been coming for years, who re-wear the same accessories every year and have their own timeless style statement. There are others who see dressing up as an opportunity to plan an event similar to your look for a family wedding. Many have spent weeks or months preparing, often recruiting personal stylists such as Sarah Byrne and Annie Miall, who specialize in the genre.
“With the Gold Cup anniversary this year, it feels especially celebratory,” admits Jade Holland Cooper, founder of the eponymous countrywear label. “Cheltenham is a time for heritage style – it’s a beautiful chic look. Dress code is wordless [not officially set by The Jockey Club, like Ascot]but his knowledge and understanding are now so.”
Holland Cooper knew months ago that she would be wearing an emerald houndstooth outfit on the first day of this year’s event – an ankle-length skirt and matching coat.
“My goal every year is to move the look forward and always keep that timelessness,” she says. “We are evolving the classics. You could wear the same silhouette every day and update it with just the fabrics if you wanted to. The possibilities of traditional materials are endless – you can go wild in graphic pink tube, or smooth in black and white herringbone.”
For men, Holland Cooper’s ‘Cheltenham edit’ covers Prince of Wales check coats and woolen gilets, ‘tawny’ blazers with matching caps. “It’s elegant classics, with a bit of Peaky Blinders magic thrown in,” she says.
Holland Cooper is one figure at the heart of Cheltenham’s social team. The event brings together racing royalty (Rosie Tapner and Francesca Cumani) with actual royalty (Zara Tindall and Queen Camilla) to create an eclectic crowd. A coterie of country designers come with their ideas, socialites from the city to their country homes for a week of fun.
As celebrity culture in the Cotswolds has certainly grown in recent years, nearby Cheltenham also has a ‘foreign’ interest. The festival now attracts its share of fashion show ponies – those who are here for dress up and a day out. And why not? Last year’s country stars included Matt Hancock and Carol Vorderman, as well as half of the Love Island cast. They all knew exactly what to wear – how could they not?
“Obviously the racing is fantastic, but it’s also a huge social event,” says Francesca Cumani, ITV Racing’s caretaker. “There is no formal dress code at Cheltenham, but in my opinion big race days always deserve a great outfit. I think it’s important to try. The horses always turn out flawless, so we should be as well.”
Cumani enjoys the fashion show as much as anyone – her own outfit included a fuzz-trimmed gray houndstooth coat and a neatly belted herringbone cap.
“Zara Tindall never misses a day of the festival and always looks amazing,” she says of her tips on who to watch when it comes to style. “Stylist Sarah Byrne also looks great – usually in something she’s pulled together at the last minute after everyone else has dressed.”
For Sky Sports Formula One presenter Natalie Pinkham and her husband Owain Walbyoff, Cheltenham offers a different style of race day – and a theme they fully embrace.
“It’s stuck 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 mentions Savile Row women’s tailor The Deck and The Huntsman as two of her go-to brands for the occasion. “Milders like Sarah Cant also provide that creativity to see your own,” she says.
It’s good sport to see people rehashing and adapting old sayings. “Talking to a lot of women who go, I love that so much is upcycled and tailored to create different looks,” she says. “These are custom pieces that are passed down through families and customized to fit their individuality.”
The men and women of Cheltenham are challenging themselves to express their personality while dressing in theme. A great (and crucially warm) coat is the focal point of any outfit, but it’s the additions and accessories that really make one stand out. This year’s official best in show will receive a £4,000 Boodles necklace.
“Embracing creativity is key for racers, extra accessories add a vibrant pop of colour,” says Alice Leet-Cook, co-founder of Hicks & Brown, the millinery brand beloved by the Princess of Wales. The right headgear, she notes, “can keep the sun and rain out of your eyes while looking effortless.”
Many of the attendees travel in herds – coordinating couples in the stands is a big deal.
“It’s a great opportunity to dress up – for me I don’t care about going to the races in the past,” says Tom Joule, founder of Joules. He will wear a corduroy suit, to balance his wife Alice, who will wear the tweed.
“With over 50,000 people going to the race a day, you want to stand out in the crowd,” says Alice. “Cheltenham theater makes you want to play the part.”
Who’s who in Cheltenham style
Racing royalty
ITV racing presenters Rosie Tapner and Francesca Cumani bring color to the proceedings. Horse owners Joe and Marie Donnelly are always amazingly complex.
Real royalty
Zara and Mike Tindall never miss Cheltenham – it’s just a short trot from Gatcombe Park. Queen Camilla attended last year wearing sand suede boots and a fur trimmed hat. Princess Anne usually wears a colorful silk scarf over her brown and gray checks.
The rural vogue designers
Jade Holland Cooper (wearing a skull on her own label) usually comes 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 dressed their part. For Marcus Fairfax Fountain, co-founder at Fairfax & Favor, it’s a side sport to see how many in the crowd are wearing his brand’s signature Sienna cap.
The country-city commuters
Another category of attendees are those who mix quite seamlessly and regularly from city to countryside; Georgia Toffolo, Natalie Pinkham, Luke Evans. Their wardrobes in their home (or homes) must hold sections for every lifestyle.
Just a horse around
They are here for the day out. It’s Carol Vorderman, it’s Gareth Gates, it’s the cast of Love Island. But they have certainly communicated the dress code, in brogues and checks.
Download Cheltenham scene. .
Suffolk fedora, £99, Hicks & Brown; Newsboy cap, £69.95, Schoffel
Gina suede top, £295, Fairfax & Favor; Single breasted blazer, £599, Holland Cooper
Bloomfield silk scarf, £39.95, Juliet
