What to wear to Cheltenham Races – outfits for ladies and gents

You’ve got the dates in your diary, but now you’re wondering what to wear to Cheltenham races. With Cheltenham Festival on the horizon, we’ve put this guide together to help you find an outfit that will look the part and have a great day.

The racecourse can be understandably wet and windy during the winter months, and many first timers can get caught out by the conditions. This guide is full of tips on what to wear and will help you get an idea of which looks are popular.

H&H’s racing editor Jennifer Donald regularly attends Cheltenham Festival and advises that knowing what to wear to Cheltenham is not all about fashion.

“The four-day Festival is always a trade-off between style versus warmth, practicality and comfort in order to stay the distance. If you start out in heels on Tuesday, by Thursday you’ll likely be crying out for some sheepskin-lined slippers.”

What is the Cheltenham Racecourse dress code?

Cheltenham Racecourse has no official dress code – it’s not like the super-strict Royal Ascot dress code. However, attendees are advised to dress smartly without compromising practicality and consider the unpredictable British weather. Cheltenham is all about country glamour.

The team at Cheltenham offer one very simple piece of guidance, which is to come “dressed to feel your best” and many racegoers still choose to dress up for a day at the races. Even though it’s not mandatory, getting dressed up is part of the day for most attendees.

What to wear to Cheltenham races: the considerations

• Weather – much of the excitement at Cheltenham is outside, and with many uncovered areas, it’s important you’re dressed for the weather. It can be wet and windy.
• Time of year – Cheltenham Festival is held in mid-March, but there are other meetings throughout the season between October and May
• Enclosure – at Cheltenham, people get dressed up no matter which enclosure they are in. During the Festival, fancy dress is not permitted in hospitality, restaurant facilities, or in the Club Enclosure (check your Cheltenham tickets). Fancy dress is permitted in other areas as long as the outfit isn’t offensive, and at the racecourse’s discretion, they reserve the right to decline entry, should the need arise.
• Time of day – races are held each day during the afternoon, so it’s definitely worth taking a jacket to cover up and keep you warm

What to wear to Cheltenham races: the specifics

Jump to:

• Ladies’ dress advice
• Men’s dress advice

What ladies should wear to Cheltenham

We’re all unique, and no more so than in our sense of style and comfort. Although there is no official Cheltenham Festival dress code, you might prefer to turn heads with a glamorous dress or trouser suit.

But whatever your taste, the most important thing when choosing your outfit is, of course, comfort and confidence. Wear what feels right for you and it will keep you feeling your best, whatever the weather. Follow our useful tips and advice on what to wear to Cheltenham races so you can enjoy your time at the races.

Jennifer Donald says “Some of the best outfits I’ve seen over the years have combined the traditional Cheltenham look with something out-of-the-ordinary, such as a striking, but not too ostentatious, hat, a colour pop from a smart coat or covetable accessories.”

As a regular spectator, Jennifer has some go-to items. “A solid investment has been a pair of Dune knee-high suede boots [like these] that are both divinely comfortable and smart enough to look dressy and they’ve already seen me through several race meetings, so they’ll be making a couple of appearances at Prestbury Park, too.

“My two other best investments over the years have been a long navy coat – it’s smart, goes with everything, hides multiple layers when it’s freezing and makes me feel a million dollars – and the slightly-less-glamorous thermal long-sleeved top [like this]. I promise, with one of these you’ll never feel cold again.”

Ladies’ shoes

Sensible shoes are a must as you are going to be on your feet for long periods of time throughout the day and two-thirds of the car parks are on grass, so choose something practical and comfortable. That said, there’s no need to sacrifice on style and there are so many chic options at your fingertips.

Chunkier, close-toed shoes are a great choice and heeled pumps or court shoes are elegant yet practical and easier to walk on grass. Block heels are especially comfortable. Many ladies opt for a pair of stylish knee-high or ankle boots instead. Invest in a good pair of boots that will serve you well through the colder months. Chelsea boots are also a popular choice.

Ladies’ dresses and jumpsuits

When we think of the ultimate race day look, a dress is the thing that springs to mind. The sky’s the limit in terms of style, cut and fabric – the most important consideration is your comfort and wearing something you feel good about. Cotton jersey dresses are on the casual end of the scale, while linen and cotton pop in somewhere in the middle (if it’s warm), and wool, silk, satin or velvet numbers offer the most polished look.

Another option is a jumpsuit. The styles vary from super slim-fitting, to a tailored bodice and wide-leg pant, or even a relaxed all-over fit. Skirts are also an option – and tweed is particularly popular.

Ladies’ legwear

If you’re more of a trouser person, your options are far ranging. Whether you’re after a high-waisted nautical vibe, a statement culotte or a wide-leg linen, you can build an outfit as casual or chic as you like. A wool or tweed trouser with a boot will keep the cold at bay. Dark colours disguise any mud and opting for a smooth grain leather will be easier to clean.

Jeans can be on the agenda – we can recommend bootcut, wide leg or flared styles to give your look an upmarket feel, while skinny jeans will fit nicely into tall boots.

Ladies’ tops and jackets

If you’re struggling to pair a top and trousers it can sometimes help to go for opposite fit styles for each garment. For example, pair a loose, wide-leg trouser with a more fitted top. Similarly, you can use your top to dress down a more elegant trouser to give off a smart-casual vibe. A nicely-fitted, well-made white cotton jersey T-shirt or blouse would look great tucked into a high-waisted statement trouser.

During colder weather, you have the opportunity to elevate your look with whatever you choose to layer up with. Long wool or tweed overcoats, capes or ponchos – especially those with a faux fur trim – keep you cosy while looking glam.

Ladies’ accessories

Elevate your look with accessories. There are three obvious options when it comes to race day headwear: a hat, fascinator or headband. What you choose will come down to budget, style and personal preference. Traditionally, fascinators are worn on the right side of the head. Statement headbands, fascinators and leather gloves will finish this polished style. You do not need to wear the kind of hat you’d see at Royal Ascot.

Headwear can be as subtle or as bold as you like, so consider how best your headwear can complement your outfit. If your look is thus far muted, opt for a more striking colour or style. On the other hand, if you’re already sporting eye-catching attire, opt for a more subtle hat or fascinator so as not to detract from your outfit. Look for felt-type or velvet options for a wintery feel.

What to wear for Cheltenham Ladies’ Day

Also known as Style Wednesday, it is a celebration of the glamour and glory of the Festival. You can follow our advice on what to wear to Cheltenham races above as a general guidance, but most racegoers going the extra mile for this day.

For many racegoers attending the Cheltenham Festival is a family tradition and has been happening through the generations, with fabulous fashion items also passing through. To honour and celebrate these wonderful traditions Cheltenham presents the Style Wednesday Slow Fashion Awards. The Slow Fashion awards celebrate vintage and borrowed items, as well as investment pieces that can be passed down through generations. Cheltenham encourages all racegoers to showcase their unique and personal style, and to share the stories behind their amazing outfits.

What men should wear to Cheltenham races

Although there is no official Cheltenham Festival dress code, it’s the perfect excuse to wear your best attire. Some men opt for suits at the races, while others feel more comfortable in smart jeans and clean trainers. Some retailers give advice that jeans should be avoided, but casual clothing is allowed, with organisers stating that wearing what you feel comfortable in is best. Many traditionalists wear tweed, which is a great choice for the winter, but again this is personal preference.

We’d certainly advise adopting a “dress for the weather” approach and suggest you consider which enclosure you’re in as the more expensive ticketing options lend themselves to smarter attire.

Men’s footwear

Whether you’re cheering from the stands or enjoying the bar, you’ll be on your feet the majority of the day, so comfort is key. You could wear a pair of brown Chelsea boots if you’re opting for a sports jacket, while brogues might suit the classic look. If you’re wearing tweed, opt for brown footwear, while black gives a more formal look with a suit.

Men’s legwear

Try a formal, tailored trouser in a slim or regular fit for a smart and comfortable look. But think about your material – wool, tweed or a heavier cotton twill are good choices for colder weather.

Men’s shirts and jackets

Most men opt for a classic Oxford shirt. Shirts with a collar are the obvious choice and it’s your choice to opt for a dress shirt if you wish – cufflinks are a fun accessory. If you’re not going to a full tailored suit, a suitable blazer or jacket will be what to wear to the races.

Some men like to opt for a three-piece suit, which has the addition of a waistcoat, especially if they’re in an enclosure. These look smart and add a little personality to an outfit, especially if they have an interesting lining. What’s more, they give you a layering option in changeable weather. You could also add an overcoat to your look for added warmth. It’s always better to have additional layers to hand than feel cold, especially when a long walk back to the car is involved.

Men’s accessories

Accessories truly make an outfit. Cufflinks if your shirt allows are the perfect finishing touch, while a pair of smart gloves are just the ticket on chilly race days. Try matching your belt with your shoes. A flat cap is ideal for keeping your head warm and dry. You could swap out a tie for a silk scarf, to create a cravat for a sleek touch.

Don’t leave your socks at home, and if you really want to look the part then a pair of binoculars to watch the racing will finish your look as well as add to your day.

Cheltenham Festival fashion tips

Layers – wear tights or thermals under your trousers as no one will see them, but they are designed to trap heat and keep you cosy.

Accessories – gloves will not only keep you warm but finish off your outfit, while a silk scarf in an eye-catching print will compliment your look.

Sensible shoes – a must as you are going to be on your feet for long periods of time throughout the day and two-thirds of the car parks are on grass so make sure you pick a pair that are practical and comfortable.

What not to wear to Cheltenham Festival

Something inappropriate for the weather – due to the time of year it’s all about outerwear. Stay away from thin materials and floaty skirts – this is not Royal Ascot. After all, you don’t want to get cold and not be able to warm up.

Fancy dress is not permitted in hospitality, restaurant facilities, or in the Club Enclosure. Fancy dress is permitted in other areas as long as the outfit isn’t offensive, and Cheltenham Racecourse reserves the right to decline entry should the need arise.

Make the most of your money

Picking up a new look for a trip to the races can be a pricey affair. Given that there’s the cost of travel and the price of entry, investing in a new look on top might feel like a stretch. With this is mind, here’s how to spend smartly…

• Think multi-purpose – could the boots you’d like to top off your winter race day look work in your regular wardrobe rotation? There’s nothing worse than buying something beautiful and wearing it once. Instead, think about what to wear at races in terms of your closet as a whole.
• Hit the charity shops – it’s an age-old tip but truly, you never know what hidden gems lie in these treasure troves of preloved articles
• Rent your look – wear something flashy for the fraction of the cost with designer clothing rental services, such as By Rotation. You can rent garments and accessories to upscale your look and when you’re done, simply return them. No wasted money or wardrobe space – and it’s a greener way to style yourself, too.

To stay up to date with all the breaking news from major shows throughout the year, subscribe to the Horse & Hound website

You might also like: