Cheltenham Festival: Etiquette & Style Guide

 

Cheltenham Festival is an event like no other – the electric atmosphere of this famous jump race meet has to be experienced first-hand. With a strong Irish presence each year and several Grade 1 races, it is your chance to witness the elite of the jump racing world compete at the highest level.

With Cheltenham Festival 2024 on the horizon, here we share our top tips for the Festival and advice on country clothing to achieve the ‘Cheltenham look’ so for a what to wear to Cheltenham Races guide, read on. We hope you enjoy Cheltenham as much as we do…

• The History and Prestige of Cheltenham Festival
• When is Cheltenham Festival?
• Etiquette at Cheltenham
• What to wear to Cheltenham races
• Ladies Style Guide For Cheltenham
• Menswear Guide for Cheltenham

 

THE HISTORY AND PRESTIGE OF CHELTENHAM FESTIVAL

Cheltenham Festival is one of the most famous events in the National Hunt jump racing calendar and attracts thousands of spectators each year. It offers the second largest prize money in UK jump racing, second only to the Grand National. It is your chance to see the elite of the jump racing world compete at the highest level and there are several Grade 1 races. Grade 1 races are the most prestigious of the jump racing season and feature the most talented horses.

Cheltenham Racecourse has a long history in British horse racing and today it showcases some of the world’s top race horses. At the beginning of the 20th Century, Frederick Cathcart, believed that Cheltenham should be the home of steeplechasing, just like Newmarket was the home of flat racing and he made it happen by holding the first Cheltenham Festival in 1911. Cathcart managed to agree terms with the National Hunt Committee to allow the National Hunt Meeting to occur at Cheltenham every year, and so the Cheltenham Festival was born.

The build up to Cheltenham now dominates the entire steeplechase season. One of the most anticipated races at the Cheltenham Festival is the Gold Cup. Held on the last day, it is the most prestigious and valuable race of the meet. The total prize fund for the Cheltenham Gold Cup in 2023 was £625,000.

The Festival has a unique atmosphere due to the huge Irish presence each year. The Irish have travelled to Cheltenham for generations and have had many winners over the years. Also, as the dates of the Festival fall around the time of St. Patrick’s Day, there is a fantastic celebratory feel to the event.

 

WHEN IS CHELTENHAM FESTIVAL?

The four-day spectacle is held annually in March at Cheltenham Racecourse in Gloucestershire. In 2024 It is to be held from Tuesday the 12th March to Friday the 15th of March.

 

ETIQUETTE AT CHELTENHAM

Cheltenham has a more relaxed feel than Ascot, but that does not mean you should falter on good manners. Follow these tips for an enjoyable day:

Know some racing lingo

Of course Cheltenham is a social occasion, but you should also take an interest in the racing itself. If you get chatting to someone who has a passion for horse racing, it is good manners to show an interest and ask them what ‘the going is’ today. The going refers to the state of the ground which can affect how well a horse will run.

Have a little flutter

The races provide an opportunity to have a flutter and potentially win big on horses. Just be careful to moderate your reactions, whatever the outcome of your bet and try not to be overly competitive.

Clothing etiquette

The etiquette for clothing is more relaxed than other race events but there is still a ‘Cheltenham look’ that you should aim for. For more style advice for ladies and men, see our ‘What to wear to Cheltenham Festival’ guide.

Fancy dress is banned from the Club Enclosure for the duration of the Cheltenham Festival. Although you may wear fancy dress that is non-offensive in other areas, we would suggest not doing so to avoid the risk of being turned away.

No huge day bags

Any bag you take to the event will be searched on entry in accordance with Cheltenham Racecourse Security Policy. Do not take a handbag or backpack that is too large to the event. Only handbags and backpacks that are of an appropriate size for a day out are allowed into the enclosures. If you have larger bags or suitcases, they will need to be left in the Left Luggage facilities.

Know your horse racing

If you've never visited the horse racing before, it's a good idea to get up to speed with the history of the sport and the legends within the sport. There is no shortage of celebrated British horse races, but we'd also recommend scrubbing up on your USA horses too if you want to enjoy the full array of events on offer, such as film screenings and talks.

The SeaBiscuit Documentary

SeaBiscuit is one of the most popular race horses of all time, and when the film premiered in the UK the British Horseracing Board (who manage Cheltenham Festival) decided that they should sponsor the event. The documentary shows the life of the famed horse called SeaBiscuit, and all of the incredible obstacles that the horse and it's team had to overcome to reach the top. It was released in 2003 and was based on a book called Seabiscuit: An American Legend by Laura Hillenbrand. It was nominated for 7 academy awards and is crucial watching if you want to scrub up on your horse racing history.

The film stars Tobey Maguire and was directed by Gary Ross. You can watch it online in lots of places currently so no excuse not to check it out! It will definitely get you in the mood for the festival.

WHAT TO WEAR TO CHELTENHAM RACES

So you've bagged some tickets and now you're looking for some Cheltenham Races outfit ideas, don't panic. You're in the perfect place to to find the perfect festival outfit. Cheltenham Festival dress code isn't overly strict, but ladies usually wear smart winter outfits and gentlemen, suits with a tailored overcoat.

Cheltenham Festival has its own unique look, distinct from other race events that happen in the summer. The annual Festival attracts a smart country set and as the weather can be unpredictable in March, you should dress with practicality and warmth in mind. Cheltenham is the place for dress coats, fur stoles and smart country wear, rather than Ascot-style attire. Trilby hats, feathers and tweed are also seen in abundance.

Ladies style guide for Cheltenham

Cheltenham is all about country glamour. Resist the temptation of buying out of season clothes even for Ladies’ Day. Think smart country wear with chic accessories to get the right look.

The good news is that Cheltenham’s unofficial dress code includes garments that are much more wearable throughout the year. Rather than one off purchases for a single event, you can get more wear form everything you buy for Cheltenham. For instance, smart Fairfax & Favor boots and Anna Lascata tailored coats are not single-wear purchases and they can be worn at many other country events in the year.

Key pieces for your Cheltenham look

1) A tweed jacket or beautiful coat

An elegant coat or jacket is a mainstay of Cheltenham fashion, serving to keep you warm and stylish. Choose one that is cosy and interesting, being feminine, flattering and beautiful in some way.

The tailored Anna Lascata Alexandra and Taylor & Twill Highgrove Long Jacket both finish at an elegant three-quarter length to flatter your figure. For something different (but less weatherproof), the Anna Lascata Long Suede Coat is another stylish option.

If you are looking for something a little more robust, that will keep you warm and dry, the Chrysalis Bloomsbury Jacket is beautifully handcrafted in England. Made from 100% pure wool, from Scottish weaver Lovat Mills, available in two traditional tweeds, it is complete with an elegant satin lining, inter liner membrane for breathability and windproof zip. It can be a cold day spent at the racecourse and the Bloomsbury will mean you don't have to worry about the weather, and certainly won't have to compensate on style.

2) A silhouette skimming skirt

A skirt is a great way to smarten up your outfit and show off your country boots. A tweed skirt, or the new Anna Lascata suede skirt are great options.

Otherwise, the relaxed dress code at Cheltenham means it is acceptable to wear a smart pair of jeans and many do. White or dark fitted jeans are both popular with attendees.

Or opt for a tweed trouser for a warm yet effortlessly smart look. Our Taylor & Twill tweed trousers are real head turners.

3) Luxury knitwear

The Cheltenham organisers advise dressing for the weather and luxuriously soft knitwear is the best way to layer up. It can be still very cold in March, therefore put practicality first.

Jumpers or cardigans made from cashmere or lambswool are ideal. William Lockie offer stunning Lambswool quarter zips, roll necks, vees and crews and the extremely popular Lindsey Lambswool Poncho. Our Taylor & Twill Cashmere Collection collection offers soft sweaters in a huge variation of styles, abundance of colours, in varying thickness, textures and patterns, all handcrafted a mere 20 miles away from our shops in Kelso. A roll collar is particularly good for keeping a chill from your neck and back but in general knitwear is a great way to keep warm and at the end of the day you are there to have fun and you cannot if you are freezing!

4) Quality boots

For footwear, boots are a smart choice. Quality heeled boots will keep your feet warm and look good with skirts or trousers. Avoid court heels, stilettos or sandals as they will not be comfortable enough for all day wear and too cold. Most of the day will be spent on your feet, so comfort is vital.

Look for a boot with a good tread so you do not slip in the rain and leather or fur linings provide extra warmth. Cheltenham is not the place for your everyday or well-worn boots, instead opt for smart heeled boots in soft suede. Fairfax & Favor Heeled Regina Boots are popular at Cheltenham and for good reason. These knee-high boots have an elastic panel around the calf, a walkable 5cm heel and full leather linings. They are available in several colours and are handcrafted from supple nubuck suede.

Le Chameau have released a range of delightfully decadent long boots including the La Parisienne Boots. These boots are knee length and lace up, reminiscent of old school riding schools and so would be apt at Cheltenham Races paired with super skinny trousers and a long tailored jacket.

Another boot with a feminine, tailored design is the Fairfax & Favor Amira Boot. This over-the-knee boot adds glamour and elegance to your style with a 7cm heel. They look great worn with figure hugging jeans. The same could be said for the Albany Knee Boot by Holland Cooper, with a flat heel you may be able to last longer yet the Albany has the same elegant long length and is embellished with stunning gold detailing.

You can of course, not go wrong with a good old trusted pair of Dubarry boots, from the infamous Galway Boot to the more refined Longford and the new-on-the-scene Roundstone Boot.

5) A fedora or smart hat

A stylish hat is a great addition to a smart winter outfit. Anything from a fedora or trilby, to a cosy beret or faux fur hat looks great. If the weather forecast is bleak, choose something like a Baker Boy Tweed Cap, the wool is naturally insulating or opt for a waxed version from Hicks and Brown for water resistant assurance. Cashmere headbands are also complementary to a smart country outfit.

Alternatively, Hicks & Brown fedoras combine the structure of an elegant hat with beautiful feather details. These fedora hats are made from felted wool and come in muted tones as well as bolder colours, like the maroon Suffolk Fedora with Gamebird Feather. They are also water-resistant for protection against rain showers, meaning you may not need an umbrella.

If you choose a beret, go for one that is wool and structured in form, rather than soft. Casual or unstructured hats do not look smart enough for Cheltenham. A hat for Cheltenham is an elegant addition to your outfit, not just something to keep your head warm. However, if hats are not your thing, then do not worry as they are not essential at Cheltenham.

6) Wrap yourself in a luxurious scarf

The perfect finish to your outfit, a wrap, stole, scarf or twilly.

Add a pop of colour with a cashmere scarf or wrap, or exude country elegance with a Clare Haggas Silk Scarf. Clare produces stunning designs for her scarves, inspired by her love of the countryside in beautiful colours they are sure to grab wanted attention on any outing.

7) Finishing touches and a classic tote

The important thing for Cheltenham is to not look overdone or like you are trying too hard. Simple style is best and that applies to your accessories as well.

A leather or suede tote handbag is a good choice; large enough for you to keep all your things in as well as stylish. You can easily update your Cheltenham style every year with a new handbag without buying a whole new outfit. From a Fairfax and Favor Mini Windsor, Fairfax & Favor Buckingham bag to a classic Dubarry Christchurch Handbag, something to suit your individual style is ideal so you can use it again and again.

Coordinating will keep your look elegant, especially if you are wearing a coat in a striking colour. Match the colour of your handbag and gloves to your hat, keeping your accessories simple to let your coat be the centre-piece, without clashing.

Refinement is in the details and you can add a little embellishment to your outfit with a Clare Haggas Scarf Ring, coloured Fairfax & Favor Boot Tassels or a Mackenzie & George Belt If the weather forecast is bleak, take a good umbrella as well as a hat. You will not look good if you are wet through!

Ladies’ Day style

Cheltenham Ladies’ Day takes place on day two of the Festival and the theme changes each year. Every year there is a style competition, both ladies and men have a chance to win fantastic prizes. Some chose to dress in a single striking colour from head to toe for standout style.

Ladies’ Day lends itself to making more of an overall effort with your outfit, but practicality is still a key consideration. 

Impractical stiletto heels are not ideal for Cheltenham because you may need to walk through rain and muddy patches. Stylish heeled boots or closed toe shoes with a mid-heel are far more practical and can be just as glamorous. Your outfit should look appropriate for the weather with glamorous touches, such as a feathered hat or a bold coloured coat.

Cheltenham Ladies Outfit Ideas

In need of a little more style guidance? Our Humes Outfitters style advisors have put together Cheltenham Festival outfit ideas.

Menswear guide for Cheltenham

There may be no official dress code, but nonchalant country style epitomises Cheltenham. It is important to be dressed well but not to be seen to be trying too hard. In celebration of British clothing, traditional cloths and tweeds are the go-to fabrics which will also keep you warm on cold March days.

Country classics, like a tweed hacking jacket and moleskin trousers, never look out of place at this event. Trilby hats and smart brogues are also ideal. Just make sure you stay on the smarter side of country style, rather than going too casual and looking like you have just stepped off a Mumford & Sons tour!

Can you wear jeans to Cheltenham races? Technically yes and if this is what you would feel comfortable and confident in then that is what matters the most. However, if you can, opt for something on the smarter side. Even if that is replacing your denims with a pair of chino's or moleskins instead, paired with a tailored cotton shirt.

Key menswear pieces for Cheltenham

1) A wool overcoat

A tailored and traditional wool overcoat will set the tone for the rest of your outfit and looks effortlessly stylish. You cannot go wrong with classic tailoring at Cheltenham. Look to styles such as the Rodd & Gunn Lodestone Coat, the heavyweight wool and timeless style of this coat is a perfect match for Cheltenham.

The Covert Coat is traditionally worn at Cheltenham and is often the most popular style for gentlemen at the races. Be careful not to wear anything resembling an anorak, which would not be smart or warm enough for the occasion.

Wear your tailored coat with a wool or cashmere scarf to keep your neck warm and tie it in an old-school knot for best style, rather than a continental loop.

2) A tweed suit or tweed jacket and trousers

Tweed suits are a classic for the country gent and a fitted three-piece or two-piece suit is a dapper choice for Cheltenham. Tweed has also risen in popularity and is widely used in men’s fashion by couture houses around the world.

To fit in with the racing crowd, stay with the muted brown and green colours of traditional tweed, such as Taylor & Twill's Three Piece Suit Collection in a range of earthy tweeds. For something a little different, tweed comes in several shades and patterns and grey tweed can look just as stylish.

If a matching suit is not your thing, it is also acceptable to wear a tweed sports jacket and smart trousers at Cheltenham. A separate jacket and trouser combination can also give you more opportunity for regular wear with other items in your wardrobe. Just make sure that your jacket and trousers are obviously in different shades to avoid looking like a mismatched suit.

Your trousers must be smart and well-fitted, and moleskins, cords or tailored chinos are all good options. For your sports jacket, tweed or a heavyweight cloth is best to give you a distinguished look. Linen and light cotton crease too easily. Our collection of quality tweed jackets includes the finest handwoven tweeds from Scotland and Ireland, in both plain and checked designs.

3) Quality knitwear

Wear a layer of fine knitwear underneath your tweed jacket to add warmth without bulk. A single-ply cashmere or wool jumper is a good weight for layering. Cashmere knitwear provides a soft and luxurious layer or if you prefer wool, merino wool gives excellent insulation.

A classic V-neck sweater or crew neck will look smart underneath your jacket. Zip-necks can look too casual and patterned jumpers, too busy with a tweed suit. Opting for a plain-coloured classic jumper will give you versatility.

At Humes Outfitters, we provide some of the finest brands in men’s knitwear including William Lockie. William Lockie combines traditional knitting techniques with the latest technology to manufacture exceptional quality garments in Hawick, Scotland, the home of cashmere. Styles such as the Oxton 1-ply Cashmere Crew Neck or V-Neck and the Gordon Geelong V-Neck or Crew Neck are ideal for layering. Pair your jumper with a traditional tattersall shirt underneath for another warming layer.

4) Country boots or brogues

Your footwear is important as you are likely to be standing outside in the cold weather and can be on your feet for hours. A smart shoe or boot with a good tread for grip underfoot is best. Country brogues, laced chukka style boots or Chelsea boots are ideal.

The finest men’s boots are stocked by Humes Outfitters and include RM Williams, Loake, Dubarry, Cheaney, and Taylor & Twill. All these brands offer quality made boots that will last you many years with good care. Boots that are perfect for the modern gentleman include the Taylor & Twill Bracknell Boot, a Chelsea boot made from with a leather goodyear welted sole and a hand dyed leather upper, or La Chukka Cuir Boots by le Chameau handmade in France by master bootmakers. Also, consider the RM Williams Comfort Craftsman Boot which is handcrafted from either Yearling, Vesta or Kangaroo leather, and Dubarry’s Antrim Boots. The Antrim is one of Dubarry’s most popular waterproof Chelsea boot and includes underfoot cushioning and a moulded footbed for comfort all day. There are many men’s smart boots to choose from, just remember to wear them before the races to make sure they are comfortable for all day wear.

Alternatively, a traditional brogue shoe is another good choice. Loake has been making brogues to the highest standards for more than 130 years, using the finest leathers and featuring Goodyear welted leather soles and Cheaney are renowned for making the highest quality brogues from their factory in Northamptonshire.

We would not recommend loafers as they will not give you enough protection against the rain in poor conditions and are not sturdy enough. Always wear socks, for example merino wool over-the-calf socks. Wearing no socks would be a strange look at Cheltenham - it is not the Cowes sailing regatta!

5) A tweed bonnet

Wear a hat for practicality and sartorial style. A good hat will keep the rain off you so you may not need to carry an umbrella. A tweed baker boy hat or flat cap are classic Cheltenham Festival style. See our Flat Cap Guide on how to find your perfect flat cap.

 

6) A tie

Wear a tie as the Cheltenham Festival is a racing occasion and you will not want to look underdressed among your contemporaries.

There are many wool and knitted silk country ties for you to choose from to personalise your look. If you are wearing a bold tweed suit, select a tie in subdued colours so it does not compete with the pattern of the tweed. Do not wear a tie-bar as this would look too much like workwear and you are not attending an office meeting.

*Sources referred to for the creation of this document.