What to Wear to Cheltenham Festival

Country Tailoring for One of Racing's Great Occasions

If Royal Ascot is about summer formality, Cheltenham Festival is something entirely different. Held in March, Cheltenham brings together world-class National Hunt racing with classic British country style. This is the territory of tweed, wool, flannel, overcoats and proper footwear. And because the weather can move from spring sunshine to cold wind and rain remarkably quickly, the best Cheltenham outfits combine style with practicality.

Does Cheltenham Have a Dress Code?

Cheltenham has become more relaxed about formal dress in recent years, so a suit and tie aren't universally required. That doesn't mean you shouldn't dress well. For many racegoers, dressing for Cheltenham remains part of the occasion. Our advice is to embrace the character of the event rather than treating it like either a business meeting or a day hiking across Dartmoor.

Tweed

Cheltenham and tweed belong together. But there's much more to tweed than the stereotypical heavy brown country jacket. Consider:

• Herringbone
• Donegal
• Gun-club checks
• Windowpane checks
• Green and olive tweeds
• Brown and tobacco
• Blue and grey
• Contemporary lightweight tweeds

A made-to-measure tweed jacket can be paired with flannel trousers, chinos or heavier cotton trousers. Alternatively, a complete tweed three-piece creates a stronger statement.

The Three-Piece Suit

A three-piece suit works particularly well at Cheltenham. The waistcoat provides additional warmth while adding another layer of interest to the outfit. You might choose a matching three-piece or introduce a contrasting waistcoat. A brown or green tweed suit with a complementary waistcoat can look superb without feeling overly formal.

Flannel

Flannel is another ideal Cheltenham cloth. Soft grey flannel trousers paired with a tweed jacket are one of the great combinations in classic menswear. For something sharper, consider a complete charcoal, grey or navy flannel suit. Flannel has warmth, texture and a softer appearance than conventional business worsted.

The Overcoat

Don't treat your coat as something you'll only wear between the car and the racecourse. At Cheltenham, it may be visible for most of the day. So make it part of the outfit. A Chesterfield, covert coat, Ulster coat or tailored wool overcoat can all work beautifully. An Ulster coat in herringbone or textured wool is particularly appropriate for a country racing environment.

The Covert Coat

The covert coat has strong associations with British country clothing and racing. Traditionally cut from durable covert cloth, its clean shape makes it equally useful in town. It's a particularly good choice if you want something less bulky than a long overcoat.

Shirt and Tie

A pale-blue, white or subtle check shirt works well with country tailoring. A knitted wool or silk tie can introduce texture, while traditional woven patterns and country-inspired colours complement tweed beautifully. Burgundy, forest green, navy and rust can all work.

The Roll Neck Alternative

For a more contemporary look, a fine roll-neck knit can work underneath a tailored jacket. It creates a cleaner, less formal outfit while remaining considerably smarter than ordinary casual clothing.

Trousers

Grey flannel is the classic partner for tweed. But olive, brown, navy and cream can all work depending on the jacket. Pleated trousers with a slightly higher rise can look particularly good with traditional country tailoring. At Roomten, we're also fond of double pleats and turn-ups for this type of outfit. They give the trousers character while remaining entirely wearable away from the racecourse.

Footwear

March isn't the time for delicate summer loafers. A good pair of leather or suede boots can be ideal. Brogues and substantial leather shoes also work well. Choose something that can cope with the weather and that you can comfortably stand in for several hours.

Don't Forget the Rain

Cheltenham weather is unpredictable. A proper raincoat or waterproof mac that works over tailoring is worth considering. A field coat can also provide a more relaxed alternative.

The Roomten Cheltenham Look

Our classic Cheltenham outfit would be: A brown or olive herringbone tweed jacket, mid-grey flannel trousers with pleats and turn-ups, pale-blue shirt, textured tie, brown leather boots and a long tailored overcoat. Or take it a stage further with a complete three-piece tweed suit. Cheltenham is one of the few major events where heavier British cloths really come into their own. Make the most of it.

Dressing for Cheltenham?

Roomten can create made-to-measure tweed jackets, three-piece suits, flannel trousers, waistcoats and overcoats for Cheltenham and the wider racing season. Book a Roomten consultation and create your Cheltenham outfit.