The fashion spotlight shone brightly during Cheltenham Festival 2026 Ladies Day, where racegoers gathered not only for top-class racing but also for one of the meeting’s most anticipated style traditions. Among a sea of colourful hats and elegant coats, it was Megan Cunniss from Galway who captured the judges’ attention to be named Best Dressed.
The 29-year-old medical secretary, attending the Festival for the first time, impressed with an outfit she had personally designed. Her carefully considered look blended confidence with understated elegance, setting her apart during the celebrated style competition that accompanies the action on the track.
Cunniss revealed that instinct played a part in her choice of attire. “It’s my first time at Cheltenham. I used to always watch it on the telly, and now I’m here,” she said with a smile. “I designed the outfit myself. I don’t know exactly how much I spent on it, but a lot.” Her designs, she explained, are part of a collaborative effort with her husband. “My husband draws up my designs. We work with a manufacturer in the Middle East, and he makes all our outfits.” The decision about which outfit to wear on the day almost went a different way.
“My husband and I were arguing because he thought I should have worn another outfit today, but I had a good feeling about this one,” she said. “Even without the Best Dressed it was a special day. I’m happy with the Best Dressed title and thrilled with the prizes.”
For winning the Cheltenham Festival 2026 Ladies Day Best Dressed competition, Cunniss received a Boodles Roulette Long Mini White Gold Necklace and a £500 Holland Cooper voucher. Her prize collection also includes an Atelier experience and tickets to several major racing events next year, including the Randox Grand National Festival 2026, the Betfred Derby Festival 2026, and the Cheltenham Festival in 2027.
Cheltenham Festival 2026 Ladies Day Style Awards Celebrate Racegoers
Fashion was not limited to individual honours. The newly introduced Best Dressed Duo award went to Julie Harries, 55, and her daughter Elin, 19, from Carmarthen in Wales, whose coordinated look caught the judges’ eye. Their victory came as a surprise, particularly as they had already begun their journey home when the news arrived. “We were flabbergasted about winning,” Julie admitted. “We were literally on the way home and had already driven half an hour when we got the call.”
Julie added that she had been planning her Festival outfits for months. “I’m always looking for outfits for Cheltenham since last year.” Elin, meanwhile, was delighted that a favourite wardrobe staple helped complete the winning look. “I’ve worn these boots so many times,” she said. “I absolutely love them.”
The pair’s success earned them an overnight stay for two at Ellenborough Park in a Deluxe Bedroom with Spa Garden Retreat, along with hospitality for two at a Cheltenham Racecourse fixture during the 2026/27 season. Their prize package also includes tickets to the Cheltenham Festival 2027, the Randox Grand National Festival, and the Betfred Derby Festival 2026.
Asked if they would attend those events together, Elin responded with an immediate grin: “Of course.” Another highlight of Cheltenham Festival 2026 Ladies Day came with the Best Dressed Group award, which was presented to Tanya Hockin and her friends Sarah, Callum, Karen and Sue. The group were making their first visit to Cheltenham after regularly attending Ladies Day at Ascot.
“This is our first time at Cheltenham,” Tanya explained. “We usually do Ladies Day at Ascot, but we thought we’d give this one a go, and it’s been amazing.” Despite their coordinated appearance, Tanya revealed their look had come together naturally. “We literally just rocked up like this,” she laughed.
Their stylish effort earned the group an array of prizes, including six covers in the Panoramic Restaurant at Cheltenham Racecourse on Saturday 13 December. They also secured an Ellenborough Park spa day with treatments and exclusive use of the Spa Garden, plus tickets for next year’s Cheltenham Festival and leading racing fixtures across the season.
Judging duties for the style competition were carried out by presenters Rosie Tapner, Frankie Foster and Ellie Evelyn Smith, who selected the winners after reviewing a wide range of imaginative race day outfits.
As Cheltenham Festival 2026 Ladies Day once again demonstrated, the meeting’s traditions extend beyond the racing itself. The Festival remains as much a celebration of style and social occasion as it is a gathering of the sport’s finest competitors.
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