How to dress like a royal at Cheltenham

Telegraph

10-03-2025

The Cheltenham Festival draws over 65,000 racegoers every March, making it one of the biggest events in British racing. It's a four-day spectacle of thrilling racing and countryside chic, with enough Guinness flowing to fill three Olympic swimming pools.
Unlike the formal dress codes of events like Royal Ascot, Cheltenham doesn't impose any official style rules in any of its three enclosures. As Jade Holland Cooper of Holland Cooper notes: 'Cheltenham represents tradition, heritage, and sophistication; it really is the ultimate countryside catwalk.' –
Dressing for Cheltenham is about practicality as much as style. With unpredictable British early spring weather, sturdy shoes and boots replace heels, and layering with gloves and weatherproof outerwear is essential. Paired with the traditional formality of racing events, it's a unique set of criteria that peaks on 'Style Wednesday', offering an off-track fashion showdown.
Despite these challenges, it's possible to strike the perfect balance between chic and practical and no one does it better than the Royal family. Since the early 1900s, members have made their mark at Cheltenham. There was the Queen Mother in 1987 wearing her signature blue; Diana, Princess of Wales turned heads in 1982 when she wore a red mohair coat while pregnant with Prince William. The late Queen wore the likes of Hardy Amies and our current Princess of Wales stunned racegoers in 2013 wearing a blush pink Joseph coat, as did our current Queen in a chic wide brimmed faux fur hat in 2023.
In fact, whether you'll be in the Guinness Village or up in a box, there is no better starting point for outfit inspiration. Read on for our essential guide...
Your coat is key
At Cheltenham, a coat is your first line of defence against the elements, so invest in one that's warm, weatherproof, and of course stylish. 'When it comes to outerwear, wool or tweed coats are essential, says Hillary Bacon, marketing director of Cordings. 'An overcoat is a classic option, but whatever you choose, ensure it's sturdy enough to shield you from the often bracing winds.'
A well-tailored long or knee-length coat, or a coat dress, in a neutral tone is timeless and versatile, easily paired with accessories again and again. The Princess Royal, for instance, wore the same coat in 2007 and 2024.
For a contemporary look, try a tailored trouser suit or cape as favoured by Zara Tindall. Layer a cashmere roll neck underneath in a tonal colour for warmth to and keep things sleek.
Alternatively, you could channel a look seen on the now-Princess of Wales in 2007 – a skirt suit, a look that's gaining traction at the moment as spotted recently on Anna Wintour and Anya Hindmarch.
Embrace colour
In addition to your choice of outerwear, the colour you choose is just as important. Stylist Alice Hare notes: ' Tweed, tweed, and more tweed is the unspoken dress code of Cheltenham. Accessories are the perfect way to inject modernity and drama into a traditional fabric. If you're not keen on tweed, stick to earthy tones to avoid looking out of place.' In 2006, The Duchess of Edinburgh added jewel tones by matching her buttons to her hat and bag. Stick with a traditional colour palette and elevate it with a patterned scarf or hat, or allow a statement check coat to take centre stage, complimented by tonal accessories such as a pair of leather gloves. Take inspiration from the late Queen Elizabeth II, who wore a blue check coat in 2003.
Sensible footwear is a must
When it comes to footwear at Cheltenham, practicality is essential. Opt for boots in neutral or dark tones that can easily complement your gloves or handbag. Leather is a smart choice due to its durability and to withstand unpredictable weather conditions. Whilst in the late 1950s heels were once considered a royal requirement, today, stylish boots or flats are the go-to for attending the festival. Penelope Chilvers advises: 'When attending Cheltenham, go for sturdy yet stylish boots. It tends to be cold and often wet, so choose ones with a good grip'. Knee-high boots with block heels are a royal favourite, offering both style and stability, no one wants to risk sinking into the turf in stilettos.
Choose timeless accessories
To elevate your Cheltenham look, consider timeless accessories like brooches and earrings. Antique jewellery historian Zuleika Gerrish of Parkin & Gerrish explains, 'A brooch isn't just for a lapel; pin it on a hat, belt, cuff, scarf, or even a bag for a unique twist.' The Princess Royal's gold horse brooch, worn across three days last year, perfectly illustrates how one piece can complement multiple outfits. Queen Camilla is also known for her sentimental brooches, like the horseshoe brooch she wore in 2024 to honour King Edward VII's racehorse 'Minoru.' In 2023, she wore a brooch similar to one owned by Queen Elizabeth II, depicting a jockey in the King's racing silks.
When it comes to earrings, keep it classic with simple gold studs or drop pearl earrings. Honour Wainwright, Director of Boodles advises, 'I find earrings are the most important pieces to wear throughout the festival. With Cheltenham's often chilly weather, roll neck jumpers and long sleeved coats can make pendants and bracelets less visible. Earrings, however, always stand out - enhancing an outfit while remaining practical, even in the most unpredictable conditions!' For a more contemporary look, Zara Tindall sometimes opts for chunky earrings, complimenting her outfits, especially when wearing modern styles like a trouser suit.
Seek a polished finish
As you are usually layered up, a knockout look is heavily reliant on a good hat or bag. Renowned milliner, Rachel Trevor Morgan says: 'I would always recommend a felt or wool hat as the weather can be very variable and windy. Opt for stylish, stand out felts with a more wintry feel. Keep it simple but go for a strong silhouette. Feathers are also a great option either as a trim or a headpiece.' Queen Camilla and the Princess Royal are often seen wearing wide-brimmed styles to classic pillboxes. For an alternative to wider-brimmed hats, Zara Tindall often opts for more structured, contemporary styles in a pop of colour.
Additionally, a structured leather bag, crossbody or clutch is just as important and keeps you hands-free for a glass of champagne or your racecard.
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