The Cheltenham Festival in March is the highlight of the National Hunt Season with over £4m of prize money. This year this four day festival starts with the Champion Hurdle on Tuesday 11th and ends with the Gold Cup on Friday 14th March 2025.

All prices are correct at time of publishing.

Official Dress Code

Officially there is no dress code – their motto is ‘Dress to feel Your Best’ even if that is a nice sweatshirt, pair of jeans and clean trainers. However for a big race meeting such as The Cheltenham Festival most racegoers choose to make an effort.  Whichever you decide, remember to dress for the weather. 

Fancy dress is not permitted in hospitality, restaurant facilities, or in the Club Enclosure. It 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. Sports team kits are not permitted.

Gentlemen We Say…

Dress for the weather, dress for warmth, layering is your secret style tip when considering what to wear to Cheltenham Racecourse, as well as other courses! – And why not enjoy the occasion as an opportunity to dress up and have fun? Sartorial flair is associated with the major racecourses and after all, Cheltenham is the ‘Home of Jump Racing’. 

Cheltenham Festival x Holland Cooper

Holland Cooper is a Cheltenham Racecourse and Festival Fashion partner. They specialise in fine good tailoring using heritage methods and heritage fabrics. One of their three-piece tweed suits would be  a great investment for The Cheltenham Festival

Their Single Breasted Blazer has been crafted in UK mills from Scottish tweeds – Clarence Check Merlot. With classic notch lapels and neat horn buttons to fasten, the contrasting under collar makes for a contemporary twist. Satin twill lining and double welt pocket detailing. Finished with traditional Holland Cooper detailing, braided lapels and practical chain hanger loop. Available in plain navy, various check and herringbone tweeds including the Clarence Check Merlot £599.00 Pair with their matching fully lined Classic Trouser   £399.00 and for additional warmth the matching St James Waistcoat £349.00 Instead of a shirt wear the warmer Byron Roll Neck Knit in 100% Merino wool Available in moss, chocolate, charcoal, navy or black £139.00. Add another layer of warmth with Lightweight Monogram Scarf in Light Camel Forest Green) £99.00 Step out in their Chelsea Boot with a resin rubber outsole for durability and grip. Available in chocolate and black. £299.00 Choose their sartorial Sock Gift Box £49.00 for 3 pairs Available in charcoal or chocolate houndstooth. Experienced Cheltenham racegoers will emphasise how cold it can get there if you spend the day outdoors, and this is where a warm overcoat will pay dividends.  Holland Cooper has the aptly named Cheltenham Coat The Cheltenham is a single-breasted mid-length coat with slightly padded shoulders for a sharp silhouette. Features classic notch lapels and horn style button fastenings. Pop the collar to reveal our hidden fabric detailing that matches the internal double-welt ticket pocket. Finished off with functional cuff button detailing and branded alloy-finish coloured buttons. Available in various colours and checks. £849.00 A cap will complete your dapper outfit especially if you are wearing a tweed suit or a wool overcoat, plus it will also keep your head warm and dry. Similar to the flat cap is the popular and more youthful Baker Boy or Newsboy cap which is fuller and panelled with a button on the top. Holland Cooper Baker Boy Cap is available in a variety of colours and tweeds including Tawny £79.00

Debenhams x The Jockey Club Partnership

Debenhams, the Digital Department Store, has joined forces with The Jockey Club in an exclusive two-year partnership. As The Jockey Club’s newest Associate Partner, For one week only during the Cheltenham Festival, Debenhams will set up a Day Spa at The Orchard™ where Cheltenham Festival-goers in the Club Enclosure, will be treated to complimentary hair & makeup touch ups. Debenhams offer a great choice of outfits for a day at the races including tweed suits and blazers. Tweeds add colour, texture and patterns that a normal business suit can’t. 

Grey Herringbone Harris Tweed Jacket by Dobell £346.99 Harris Tweed is the only fabric still woven by hand and made from pure virgin wool dyed and spun in the Outer Hebrides. To regulate and protect the fabric against imitations, the Harris Tweed Orb certification mark was created in 1909 and is the oldest British mark of its kind. So when buying Harris Tweed, check it has the certification mark. Add an extra layer with Dobell’s matching Grey Herringbone Harris Tweed Waistcoat £104.99. Wear with their matching Grey Herringbone Harris Tweed Trousers £157.99. Not only will you stay warm and strike a sartorial pose in a three piece tweed suit,  it can look equally dapper when worn separately. For a quirky look wear the trousers and waistcoat together but add a different coloured tweed jacket, wear the jacket and waistcoat with a pair of jeans or wear the jacket and trousers and change the waistcoat to another tweed or a block colour woollen waistcoat. For a youthful smart casual look team with a washed denim shirt. Or go classic chic with Mock Neck Sweater by Calvin Klein  In 100% Merino wool for warmth and coolness. Was £120.00 now £96.00  Traditionally brogues are worn with tweed and they are also good for walking on soggy ground, after all this hardy shoe came from soggy origins. Originating in Scotland and Ireland, it started as a heavy untanned leather with perforations which were not for decoration but to allow water to drain from the shoes whilst walking through bogs and other wetlands. It became a country walking and sports shoe when the gentry saw the benefits. Thomas Crick’s ‘Nesser’ Ankle Derby Leather Brogue Boots have a cushioned footbed and durable rubber sole. Available in black, tan and burgundy leather. £49.99 Wear with Heat Holder’s Thermal Waterproof Socks with Fleece Lining These black socks are 100% waterproof warm and breathable. £35.99 If wearing an overcoat make sure it is large enough to fit comfortably over your tweed suit. Steel & Jelly’s Ryburn – Double-Breasted Oversized Overcoat , reaches just below the knee for extra coverage and warmth. Features inner & outer pockets. In charcoal Was £135.00 now £108.00 , Accessorise with Infinity Leather’s vintage retro style  Peaky Blinders Newsboy 8 Panel Hat in charcoal. Available in other colours. Was £25.79 now £19.99 And dont forget a pair of their Leather Warm Wool-Lined Winter Gloves – Marquis  in black but also available in navy or tan. Were £33.99 now £28.99 Add a pop of colour with Wool Fringed Scarf by Savile Row Company London in bright blue. Also available in light tan and black. 100% virgin wool. £39.95

Tweed

Tweed is the favourite fabric of any winter racing event and comes in many shades, thicknesses and patterns. So how do you choose?  Smaller guys (short or in weight) should avoid the larger checks as these will just drown their frame. Go for the smaller checks.The more textured tweeds are heavier so will add bulk – good for the skinnier guy. The heavier or more rounded guys should go for the less textured tweeds and the less structured soft tweed jackets.Tweed traditionally comes in muted earthy and autumnal colours which suit men with warm and muted colouring. Keep the warm muted colouring with shirts and jumpers to complement the look such as a cream shirt or orange jumper. 

For men who have a cooler and bright colouring, never fear as there are tweeds in blues and greys such Walker Slater Borders Tweed Edward Jacket  in navy of light grey herringbone window pane. Also available in the warm shades of mustard and peat to suit the men with warmer colouring.  £375.00 Team with matching their Edward Trouser in Borders Tweed Herringbone Windowpane £185.00 and Edward Waistcoat Borders Tweed Herringbone Windowpane £125.00 The Borders Tweed is lighter than the traditional tweed so ideal for transitioning from winter into spring. It is Worsted Spun – meaning twisted- from a longer yarn and the blend of fine merino wool offers a soft, comfortable fabric. The pattern is a combination of both Herringbone & Windowpane. Herringbone, also called broken twill weave, is a V-shaped weaving pattern. It is distinguished from a plain chevron by the break at reversal, which makes it resemble a broken zigzag. Windowpane is a large version of a graph check, where vertical and horizontal lines cross the fabric to create squares then cover the fabric. For extra warmth wear with their Muir Roll Neck in 90% Merino Wool, 10% Cashmere Available in various colours to compliment the complexion: mid blue, black, iron grey, chalk, midnight blue, wine for the cool complexions and beige, brownstone, forest green, clay, sienna, tan and hojicha (reddish brown) for the warm complexions. £110.00. Their Conrad Coat draws inspiration from the “greatcoats” of the First World War. A winter weight predecessor to the iconic trench coat, the greatcoat was designed to keep soldiers warm during blustery winters on the front lines. The large collar and below the knee length keep the wearer sheltered from the wind and rain, while the deep buttoned vent at the back provides mobility. The loose fit, extended shoulders and A-line shape allows room to layer over a jacket. The adjustable half belt at the back allows the coat to cinched in for more shape or let out, making room for additional layers. Available in cooler shades of burgundy or navy and warmer shades of fawn, camel, khaki or brown. 100% wool £565.00 The flat cap seems at home with both the trendy and the classic fashion followers. It has an interesting history: from when every male over six years old (except the upper class) was legally bound to wear English woollen caps (or else fined) on Sundays and holidays in 1571 up until 1597; to the headgear favoured by the upper class for country pursuits; and back to the city working classes in the 1920s. Walker Slater’s Rutherford Cap in Harris Tweed offers a clean, classic and sporty look. The hat’s quality and craftsmanship are inspired by the Rutherford clan’s motto: ‘Nec sorte nec fato,’ which translates to ‘neither by chance nor by fate.’ In Harris Tweed Herringbone Windowpane, colours described as Highland, Storm, Green and Slate. £58.00. Keep feet cosy in their wool Messrs Sock socks available in charcoal or brown. 80% wool £12.00 and wear with their Dixon Shoe – their take on the derby shoe, less formal than the Oxford shoe but smarter than the casual boot. A cushioned leather insole and rounded toe for comfort plus a  Blake stitched rubber sole. Available in black, dark brown or cognac. £170.00. Gloves are essential, so add some fun and colour with their  Donleavy Glove lined with 100% Shetland wool and features the  knitted fair isle pattern on the back of the glove. In navy or brown leather £175.00 Wrap up with Morar scarf made of 100% lambswool. Available in burgundy, pumpkin or seaweed. £78.00

Vintage for Slow Fashion Awards

Day 2 is Style Wednesday and Cheltenham presents the Slow Fashion Awards which encourages racegoers to ditch fast fashion and wear vintage and borrowed items instead, as well as investment pieces that can be passed down through generations. They encourage all racegoers to showcase their unique and personal style, and to share the stories behind their amazing outfits with friends, family and on social media. Vintage clothing can be found online, vintage shops and market stalls but won’t be available in all sizes. They are usually just one size so it will take a lot of searching. Victory Vintage is an online shop specialising in menswear including vintage tweed, shooting suits, three piece suits and vintage formal wear. Home

The above 2 images were available at time of print, but as there is only one sample, they may not be available long.

As new Huntsman Green tweed suit size 40 42 reg with subtle blue windowpane overcheck . The suit is made in the classic three button English cut with flat fronted trousers. The suit features a working cuff, trademark purple stripe lining,  hand sewing, hand sewn button holes, fishtail back trousers and French seams. Fit – really a big 40 in the jacket but the trousers are a little larger in the waist. Ideally the buyer would be a 41 with a slight tummy but of course the waist can be taken in an inch. If you’re a 40 and have a half decent tailor you could simply add pleats. Additionally you have brace buttons of course. Condition – As new apart from a small stain on the trouser lining waistband. £795.00 Team with their  light- Brown Christies fur felt trilby £59.00

Henry Poole heavy flannel Prince of Wales suit size 42 reg – an exceptional heavy flannel suit in classic Prince 0f Wales check by Henry Poole. The suit features a working cuff, French seam trousers, hand sewing, hand sewn button holes and high back trousers. Fit – 42 reg, slightly larger waist but not an issue with braces. Condition – As new. £945.00 Team with Grey Christies fur felt trilby size 59 fur felt trilby by Christies with 6mm brim and 11cm approx crown. £59.00an exceptional heavy flannel suit in classic Prince 0f Wales check by Henry Poole. The suit features a working cuff, French seam trousers, hand sewing, hand sewn button holes and high back trousers.

Holland Cooper images provided by Holland Cooper.

Walker Slater images provided by Walker Slater

Debenhams images provided by Debenhams

Victory Vintage images provided by Victory Vintage