Cheltenham is more than a week of world-class racing – it’s a catwalk of British style. And 2025 didn’t disappoint. From sharp tailoring to countryside classics with a twist, the Festival delivered a masterclass in how to do heritage fashion with modern flair.
Here’s our round-up of the standout style moments and what caught our eye this year.
Holland Cooper Leading the Pack
As the official fashion partner for 2025, Holland Cooper was front and centre – and rightly so. Founder Jade Holland Cooper set the tone in a monochrome houndstooth skirt suit, crisp white shirt, and slim black tie. It was sharp, tailored, and exactly what modern racewear should be.
Their outerwear and equestrian-inspired tailoring continue to be the go-to for racegoers who want to look refined without blending into the crowd.
Shop our curated Holland Cooper collection – British style, built to last.
Race Day Royalty
The Royals brought their A-game to Cheltenham this year:
• Zara Tindall paired a navy Fairfax & Favor coat and boots with a pop of yellow in her headwear – classic country with a statement edge.
• Georgia ‘Toff’ Toffolo gave a nod to Princess Diana with a red sheep jumper, mini kilt, and shooting jacket.
• Queen Camilla turned heads on Style Wednesday in a warm wool coat and faux fur-trimmed hat – adding that signature regal touch.
You can find all their looks over on The Standard.
Key Trends We Loved
Tailored Three-Piece Suits for Women
A major move this year was the rise of three-piece suits styled effortlessly by women across the course. Structured, flattering and timeless, they added a sleek edge to the traditional race day dress code – a trend championed by designers like Jade Holland Cooper.
Statement Headwear
Bigger was better when it came to headwear. Wide brims, feathers, and sculptural fascinators added personality to every outfit. You can catch a round-up of bold headwear looks on Hello! Magazine.
Modern Tweeds
Traditional tweeds were given a fresh spin with updated cuts, punchier patterns, and contemporary styling. The Times’ Cheltenham style guide highlighted how this heritage fabric continues to evolve.
Final Thoughts
At Wild & Westbrooke, we love when fashion nods to the past but speaks to the present. Cheltenham Festival 2025 was a perfect example – confident, heritage-led looks made current with clever styling and sharp tailoring.
Feeling inspired? Explore our Holland Cooper collection and build your race day look with pieces made to last season after season.
