Hurdles, hats — and plenty of tweed. Cheltenham Festival 2025 has arrived, and guests have streamed into the Cotswolds track for the third day of racing.
Georgia Toffolo was first through the gates on Thursday, pairing a kilt mini skirt with a moss green shooting jacket from Fairfax & Favor and a recreation of Princess Diana’s famous black sheep sweater by Warm & Wonderful, which has been re-created in collaboration with Rowing Blazers. The late princess wore the same distinctive red jumper at the races in 1981, and the original sold at auction in 2014 for $1,143,000.
Former footballer Peter Crouch also turned heads arriving in all all-grey ensemble, while Zara and Mike Tindall posed for cameras in a wash of tweed and olive green.
Queen Camilla lead arrivals for ‘Style Wednesday’ on the course, wearing a fur-trim beige hat with a chocolate overcoat adorned with purple and yellow pansy-style brooches on each collar.
She was escorted by Sybil Ruscoe, deputy lieutenant for Gloucestershire, to the Princess Royal stand, before joining Zara and Mike Tindall and Princess Eugenie and her husband Jack Brooksbank in the royal box.
Jade Holland Cooper, founder of Holland Cooper — one of the go-to brands for racegoers on the track —arrived in Chanel-esque, monochrome houndstooth skirt suit of her design, complete with white shirt and a thin, black tie.
On day one, it was Zara Tindall who lead the pack, and opted for a Fairfax & Favor navy coat and boots, complete with egg-yolk yellow hat. Holland Cooper, founder of Holland Cooper was another early arriver, and opted for a two-piece tweed suit with matching overcoat, blue striped shirt and yellow tie. Elsewhere, calf-length navy coats and the odd feathered headdress ruled.
Holland Cooper’s Princess of Wales approved tartan coats are a festival staple because, says ITV Racing presenter Francesca Cumani, “you’re so limited by the weather — a long coat is elegant and you can add a great belt to accentuate the waist and add a bit of interest. It’s about being creative whilst not freezing,” she says. As for suggestions: “Catherine Walker, Laura Green, Pip Howeson, The Fold, Eponine, Cleo Prickett, Suzannah London, Claire Mischevani and Alison Rodger also all make beautiful dress coats — I’d also always recommend looking in charity shops and vintage boutiques for cheaper options,” she says. For millinery, while there is no obligation to wear hats, "I love a beret in the winter — easy to wear and it won’t get blown off," she says.
Holland Cooper herself says “my top style tip for Cheltenham is to dress for the weather. It’s often chilly, so layering is key. A classic roll neck and thermals are a must-have! When it comes to footwear, comfort is everything. I opt for a flat boot or a sturdy block heel, you’ll be on your feet all day, and the ground can be unpredictable. In terms of key pieces, our signature trench coats are a timeless classic but this year, capes are having a resurgence. They’ve always been a staple in my collection, but they’re having a real moment. They offer that timeless, heritage racing look while feeling effortlessly modern. Our new Knightsbridge Cape is the perfect piece for Cheltenham: elegant, versatile, and built for race day chic.”
Marcus Fairfax Fountaine, the Co-Founding Director of Fairfax & Favor — another go-to for raceday dressing — also has tips for nailing the look. “Subtle detailing across your outfit will elevate your look while staying true to the understated luxury that defines Cheltenham fashion. A suede or leather tote in a complementary colour is the perfect finishing touch — one spacious enough for your raceday essentials, yet sleek enough to enhance your outfit.”
As for men, Fairfax Fountaine suggests they “build their look around traditional tweeds, premium suedes, and well-crafted leather pieces. They should opt for well-fitted, high-quality fabrics that provide warmth and comfort. Small touches make all the difference when dressing for Cheltenham, so they should consider elegant buttons, contrast stitching, or a statement belt to add interest to their outfit while staying true to the event’s refined aesthetic.”
The best dressed racegoers at Cheltenham Festival 2025:
Day three:
Day two:
Day one:
