How to Dress for Cheltenham Races: A Gentleman’s Guide | F. Hazell Smith

The Cheltenham Festival is one of the great events of the British racing calendar — four days of National Hunt racing in March, drawing tens of thousands of visitors to Cheltenham Racecourse each year. For the gentleman attending, dressing well is as much a part of the occasion as the racing itself. This guide covers everything you need to know.

What is the Dress Code at Cheltenham?

Unlike Royal Ascot, Cheltenham does not operate a strict dress code for most enclosures. However, the Club Enclosure and the Panoramic restaurant area do expect a higher standard of dress, and smart attire is the convention throughout. The general expectation is smart casual to smart — a jacket and trousers at minimum, with a tie or open collar both acceptable.

The Jacket

A well-cut jacket is the foundation of the Cheltenham look. For the Festival in March, the weather in Gloucestershire can be cold, wet, and unpredictable, so a tweed or wool jacket is the most practical and stylish choice. Herringbone, check, and houndstooth patterns all work excellently at the races and are particularly well-suited to an outdoor sporting occasion. Browse our selection of men’s jackets and blazers, including a range of tweed options.

Trousers

Cord or wool trousers in grey, navy, or earth tones pair beautifully with a tweed jacket. Avoid overly slim cuts — a well-cut regular or slightly tapered trouser is both more comfortable for a long day at the races and more in keeping with the occasion. Chinos in neutral tones work well for the warmer days later in the week.

The Waistcoat

A waistcoat adds warmth and considerably sharpens the look — invaluable on a cold March day at Cheltenham. A wool or tweed waistcoat in a complementary pattern or plain colour works perfectly under a jacket, adding a layer of insulation without bulk. View our range of men’s waistcoats.

The Overcoat

An overcoat is essential at Cheltenham. March in the Cotswolds can be bitter, and the course is open to the elements. A classic camel or charcoal overcoat over a jacket and waistcoat is not only practical but looks extremely distinguished on the racecourse. A Crombie-style coat or a tweed overcoat are both excellent choices. See our full range of men’s overcoats and coats.

Shirts and Neckwear

A classic Oxford cloth or twill shirt in white, blue, or a subtle check is the ideal base for the Cheltenham look. A tie in a repp stripe, wool, or subtle pattern adds formality without being out of place. Alternatively, a well-chosen cravat or a roll-neck under the jacket works well on the colder days. Explore our shirts and accessories and neckwear.

Shoes and Boots

The ground at Cheltenham is invariably soft in March. Leather Derby shoes or brogues are a solid choice and will see you through the day if the weather cooperates. Many regular racegoers choose Chelsea boots or even country boots for the wetter days — practicality must be weighed against formality at a racing festival. Ensure whatever footwear you choose is polished and in good repair. See our range of dress shoes.

Hats at Cheltenham

A good hat is both a practical accessory at Cheltenham and a sartorial statement. A flat cap in tweed or wool is the quintessential choice — it suits the occasion perfectly, keeps the wind off, and photographs beautifully. A trilby or a fedora are also well-received. Ladies Day (day two of the Festival) sees more elaborate millinery, but gentlemen tend toward the understated. Browse our selection of hats and flat caps.

A Note on Colour

The racecourse is not the place for muted, invisible dressing. Earthy tones — rust, forest green, navy, camel, mustard — work superbly in a racing context and photograph well against the green of the course. A bold pocket square, a contrast lining on a jacket, or a striking tie can lift an otherwise restrained outfit considerably.

Getting Ready for Cheltenham with F. Hazell Smith

We are just 20 miles from Cheltenham Racecourse, and each year we help many Warwickshire and Worcestershire gentlemen prepare for the Festival and Gold Cup Day. Whether you need a complete outfit or simply want to add a jacket, waistcoat, or hat to an existing wardrobe, visit us at 73–75 Regent Street, Royal Leamington Spa. Call 01926 421768 to check stock before making the journey.

Related reading: Men’s Jackets & Blazers | Men’s Waistcoats | Men’s Overcoats | Hats & Flat Caps