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Cheltenham Festival 2025 Style Guide
3rd March 2025
Cheltenham Festival 2025 Style Guide
One of the most hotly-awaited events in the British racing calendar, The Cheltenham Festival features four days of breathtaking, world-class jump racing. Attracting huge numbers of crowds, this beloved event is the perfect opportunity to wear your best, enjoy fine hospitality and of course, have a flutter or two.
Find out everything you need to know about what to wear to Cheltenham in our expert guide, compiled by the country-loving team in the know at Rufford’s.
Anyone who’s been to Cheltenham will tell you it’s special. Racing at Cheltenham was born over 200 years ago. The pinnacle of National Hunt racing, The Gold Cup, dates back to 1924. This most famous and prestigious of races takes place on the final day of the festival, and is preceded by three days of magnificent race action.
A big social affair, attending Cheltenham is an exciting experience. There’s a shopping village with many tradestands including our favourites Fairfax & Favor, Holland Cooper, Hicks & Brown, Mackenzie & George, Dubarry and Clare Haggas.
If you’re partaking in hospitality you’ll eat and drink to your heart’s content in one of 13 restaurants overlooking the course or winners’ enclosure. If you’re hoping to spot a member of the Royal Family or two, you might be disappointed; the Royal Box is well hidden away from the other private boxes, and well-guarded. You will though be treated to the rousing sight of the bright green racecourse set to a stunning hilly backdrop – an amazing setting for a succession of thrilling races and an electric atmosphere.
When is The Cheltenham Festival?
The four-day Cheltenham Festival is held annually in March. The 2025 Cheltenham Festival will be held from the 11th to 14th March.
Where is The Cheltenham Festival Held?
The Cheltenham Festival takes place at Prestbury Park Gloucestershire, a five-minute drive from Cheltenham town centre on Evesham Road.
Ladies Style Guide for The Cheltenham Festival
When planning your races outfit, there are three key things to first think about: dress code, weather and walking. Once you’ve covered these, it’s time to have fun dressing up and looking your best.
Follow the True Code
The official Cheltenham Races dress code is simply ‘dress to feel your best’ and for Cheltenham Festival specifically, there is no official dress code. Racegoers, however are advised that smart is preferable.
Unofficially, the code is a lot less ambiguous. Cheltenham is the classic country meet and nowhere else will you see more tweed, wool, leather and fur. That said, in more recent years – aided by modern British brands such as Holland Cooper and Fairfax & Favor – Cheltenham style has evolved. If wearing very traditional country clothing makes you feel frumpy, feel free to add a touch of glam and your own personal flair for a look that says ‘traditional with a twist.’
While you’ll feel more relaxed and comfortable if you adhere to the basic code, do personalise your outfit a little, too.
Watch the Weather
Really, while you can keep an eye on what the weather’s going to be like over the four-day festival, this is mid-March and you can pretty much guarantee it’s going to be cold. With this in mind, dress accordingly – there’s nothing worse than shivering your way through the day. Wrap up in materials like tweed and wool, layer up and always wear a decent pair of opaque tights. In the rare event the sun does make an appearance, you can always cast off your coat.
The exposed racecourse is notoriously windy – it’s often compared to the wind-ravaged track at Silverstone – so do also consider a tippet or scarf, and your hair. A pinned-up or back style fares better when it gets gusty, and a hat can be a great hair saver.
Get Your Walking Boots On
No, not the hiking variety. It’s time to showcase your favourite Fairfax Regina’s or Holland Cooper Albany’s. In our opinion boots are an infinitely better option than shoes at Cheltenham Races. A chunky heel is always preferable; you’ll sink into the grass in spikes.
Of course, if you’re planning on staying at your table or in your box and not getting close to the race action, it won’t matter so much what type of heel you choose. In our own experience though, even in hospitality boots – long and ankle – are more commonly worn than shoes.
If you fancy checking out the shopping village you’ll also be doing a fair bit of walking. If your footwear is new and it’s going to be your first time wearing it, we recommend breaking in the leather a bit before the event – and taking blister plasters! You don’t want to be limping by the end of the first race. To prevent cold feet, thicker socks are a must.
Here are some of our top shoe recommendations to keep you looking chic while staying practical.
Fairfax & Favor
All About the Coat
If ever you needed an excuse to invest in a beautiful, timeless coat or jacket, Cheltenham Festival is it. Make a beeline for a tailored number you simply can’t go wrong. We especially love the Holland Cooper Highgrove Chocolate Herringbone and the Knightsbridge Blazer. Another stylish choice is the Barbour Hollie Wool Jacket in Spiced Pumpkin or the classic Barbour Beadnell Wax Jacket in Sage.
For inspiration, look to the designer herself. Last year, Jade Holland Cooper styled a smart tweed blazer featuring her signature gold-crested buttons, layered over a matching waistcoat and shirt. Paired with on-trend wide-leg trousers, she put a unique, feminine spin on a traditionally masculine look.
Shop our top picks for Blazers and Jacket’s here:
Whatever British heritage coat or jacket you choose, make sure it’s in a muted palate to fit the season. Neutrals such as camel, navy, olive green and cream form the basis of your Cheltenham outfit and will last far beyond this season’s race meet. Houndstooth and tartan are also great options, pairing chic, classic patterning with timeless tradition.
The Romance of a Hat
How a hat makes you feel is what a hat is all about said Irish milliner Philip Treacy. If you feel stylish and comfortable wearing a beautiful hat, Cheltenham is the perfect place to do so. Some women do opt to wear fascinators; especially on ‘Style Wednesday (the second day of the festival was renamed from Ladies Day last year) but if you’re not sure, keep it simple with a classic fedora.
At Rufford’s Country Lifestyle, we carry a range of stunning, luxury fedoras by British labels Hicks & Brown and Holland Cooper so you can look the part. Many feature gamebird feathers or sleek leather bands, referencing the country theme and upholding a level of genteel formality often lost at modern race days.
Shirts & Skirts: A Winning Combination
A smart shirt paired with a tweed or wool skirt is a timeless race-day look. Whether you prefer a classic tailored blouse or something with a little frill and detail, a crisp shirt brings effortless elegance to your Cheltenham outfit. A high-neck blouse under a structured blazer can add a refined, feminine touch, while a fitted shirt tucked into a high-waisted skirt creates a flattering silhouette. When it comes to skirts, opt for midi or knee-length styles—both stylish and practical for the season. A-line or pleated designs work beautifully with boots, offering comfort while maintaining a polished appearance. Finish off your look with a belt to define the waist and elevate the outfit with a touch of sophistication.
Our top picks for the best shirt and top combinations.
Men’s Style Guide for The Cheltenham Festival
Why should the ladies have all the fun deciding what to wear to the races? Just like British women’s fashion, men’s English country clothing has enjoyed a resurgence and there are more brands than ever to select from.
Be a Gent
Bring out your best tweed, wool and leather; the festival is a smart, proper event. Cheltenham is National Hunt racing, not flat racing, and the hunting, shooting and fishing fraternity is out in force. You can put the sock garters away, but do dress with more than a nod to tradition.
Just as the girls are advised to refrain from bare legs and thin frocks, you’ll want to be weather appropriate in the right fabrics.
An Iconic Coat
Tweed is a winner—just like wool, it looks effortlessly dapper while also repelling water. Pair it with a smart umbrella, and if the rain starts falling, you might just become the most popular man in the crowd!
If you prefer a more contemporary look, a double-breasted smart blazer over a coordinating suit adds a sharp, distinguished touch. Ultimately, the key is to wear what feels right—if the country squire aesthetic isn’t for you, simply adapt your outfit to suit your style.
Country Shirt
Underneath, you can’t go wrong with a traditional country check shirt by Barbour, RM Williams or Gant. If it’s particularly chilly out and you plan on spending a lot of time down by the rail, add a cashmere or merino sweater for a warm, luxurious touch. We like Holland Cooper’s Byron Crew Neck Knit and the Essential Lambswool V-Neck and Loyton Merino V-Neck, both by Barbour.
Give special thought to your feet; the right boots or shoes make or break an outfit. A pair of Barbour Patton Chelsea Boots or RM Williams Craftsman Boots offer an on-point combination of refined country style and comfort. Do wear a warm pair of socks – the last thing you want is freezing feet. It should go without saying that trainers are a hard no.
Showcase those Accessories
Carefully-chosen country accessories will make your men’s races outfit stand out in the right way. A woven silk shooting tie by Atkinsons in a beautiful, eye-catching shade hits just the right tone. Try contrasting your tie with your jacket, and tucking a complementary pocket square into your jacket. Lots of men like to don trilbies and cashmere scarves for that quintessential ‘I belong in the owners’ enclosure’ look (many do).
Add an elegant pair of cufflinks and your favourite watch, and you’re good to go.
When planning what to wear to Cheltenham Festival, remember that with the exception of Style Wednesday when the fashionistas come out, less is usually more. Yes you can inject a touch of glamour and get dressed up – some of the Royals are in attendance after all – but this is not Royal Ascot.
Don’t make the mistake of looking at what people wear for summer meets. Plan for cold, start with a good smart coat and work your outfit around it. There may be no official dress code, but Cheltenham Festival is a classic country meet. Think Downton Abbey-esque – elegant country house winter weekend – and you can’t go far wrong.
Have a wonderful time!
Love, Rufford’s