Racegoers have been donning their Sunday bests (but, on Tuesday to Friday) at Cheltenham since the festival's beginnings in 1860, with everybody from royals to racing fanatics to fashion lovers, using the day to showcase their race day finery (including the best dressed guests of 2025...).
In 2024, festival bosses announced that Ladies Day - the day that traditionally encouraged women to dress to impress - would be known as 'Style Wednesday;' from thereon. The historic move demonstrates the important role fashion plays in the event, with an entire day of the sporting festival dedicated to showcasing sartorial individuality.
“Cheltenham was actually such a source of inspiration when I first started designing,” Jade Holland Cooper tells H! Fashion.
The world-renowned festival is often described as the pinnacle of the jump racing season, and Jade's eponymous brand, Holland Cooper clothing, is the official ladies' fashion partner once again. Last year, Jade and her label announced they were also confirmed in advance for the next two years, so there’s nobody we’d rather turn to for a race day style guide.
The royal-approved label, which counts the Princess of Wales as a fan, embodies the ‘elevated country-chic’ aesthetic, the epitome of Cheltenham guest style and it also boasts a stylish equine collection for riders.
© Mark CuthbertJade’s personal brand is now synonymous with her image. She’s amassed a cult following on Instagram that is a bastion of clean-cut, Cheltenham-approved fashion along with super cute content of her two children and incredibly impressive family home.
The races were an integral part of Jade’s journey when building her brand 16 years ago. "I used to look around and think there’s nothing to wear here that makes me feel chic and glamorous, warm and feminine."
© Getty"I used to look around and think there’s nothing to wear here that makes me feel chic and glamorous, warm and feminine."
If there’s one thing to note from her expertise, it's that dressing for the unpredictable British weather is of the utmost importance, but this doesn’t mean style has to compromise. Statement coats are key, as are flat boots or block heels.
Jade gave H! Fashion her ultimate style guide: golden rules for races dressing, Cheltenham vs Ascot style advice and her advice for first-time visitors.
Jade Holland Cooper's Cheltenham Festival fashion guide:
What is your go-to Cheltenham outfit?
A classic trench coat, with a roll neck underneath. I really love to wear a roll neck: they look so chic and keep you warm. It's best to pair with either a beautiful flat boot or a block heel since you may be standing on grass, so avoid stiletto heels. Gloves are a must for that extra warmth.
What advice do you have for dressing for different races, for instance, Cheltenham vs Ascot?
There is nothing quite like Cheltenham, it’s the Glastonbury of racing. A very unique, immersive experience unlike Ascot, which is all about the dress. At Cheltenham, it’s all about the coat. Go for that statement coat. My go-to is our signature trench, they are tailored to perfection, and are available in an array of classic wools and tweeds.
© PA Images via Getty Images"At Cheltenham, it’s all about the coat."
What’s your one golden rule for race day dressing?
Dress for the weather, and also be comfortable.
How did you start Holland Cooper?
I started the brand 15 years ago at Badminton Horse Trials. Cheltenham was actually such a source of inspiration when I first started designing. I used to look around and think 'There’s nothing to wear here that makes me feel chic and glamorous, warm and feminine.'
© GettyYou can be warm, but you can also look chic and classic and stylish."
I saw a gap in the market and realised I don’t need to follow fast fashion, and want to create timeless classics that will last forever. Holland Cooper is now the embodiment of racing style and the various collections now offer something for everyone. I like to cater for a broad range of ages and demographics, especially because at Cheltenham I find we are dressing women of all ages, shapes and sizes: from small accessories like a handbag or wallet to full HC looks.
Style advice for somebody who's never been to the races?
If you’ve never been racing before, it’s important to think about the weather. It’s often freezing, and you’re outside standing around for long periods of time, so it’s important to dress appropriately. Holland Cooper’s signature style is synonymous with racing fashion. It’s the unofficial dress code for Cheltenham. You can be warm, but you can also look chic and classic and stylish.
What is the biggest fashion faux pas at race day?
Not wearing layers! Layers are so important. Thermal vests under everything that you're wearing are a must to ensure you enjoy the day.
