What (not) to wear at the Cheltenham Festival

Tips from an expert stylist on what to wear at one of the highlights of the racing calendar: the Cheltenham Festival.

Over a quarter of a million people from across the world are expected to attend the four-day meetings, which culminates with the famed Cheltenham Gold Cup on Friday.

For those making the pilgrimage, there are a plethora of practical questions: how shall we get there? Where should we stay? And of course, what should we wear?

We spoke to Charlie Cooke, the in-house style expert at the fashion brand Fairfax & Favor, to get some tips.

‘Cheltenham is very much a country event and the typical attire tends to follow suit,’ says Charlie.

‘In recent years Cheltenham has relaxed official dress codes and encouraged guests to wear “what feels most comfortable”, Charlie adds — but there are a few tips:

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Don’t go too casual

‘Whilst comfort is encouraged, there are plenty of ways to balance substance with style,’ says Charlie. There is no official guidance against overly casual clothing — though football shirts and other replica sportswear is prohibited — but ‘there are choices which allow comfort without compromising on an aesthetic,’ adds Charlie. ‘Footwear choices such as tall boots give you all of the comfort you will need whilst still making a statement with your look.

‘Matching your boots to your bags is a popular trend seen at Cheltenham and for good reason, as it works so well for styling your look,’ says Charlie. ‘If you find the perfect tan handbag, look for boots in the same shade. This colour blocking will bring your outfit together and make it much easier to style.’

Pick a colour — but remember that less is more

‘Muted tones work perfectly to fit the environment of the event,’ says Charlie. ‘Look at colours like navy, tan or bottle green to really fit the brief. Having a hero colour in mind will really set the tone for your look of the day, bringing more cohesion and working wonderfully to stand out in any pictures you may want to take.

‘Try to avoid bringing too many clashing colours or prints into your look, aim for a more clean and polished look,’ Charlie adds. ‘Having fewer block colours with just a hint of patterning will make the focus be more on the overall look instead of taking attention away and onto one statement piece.

Avoid fancy dress

Don’t be tempted to plump for the sort of outlandish outfits you sometimes see at meetings such as the Grand National Festival at Aintree. ‘This is a definite no-go when it comes to Cheltenham,’ says Charlier. ‘Although the rules are very open, one specific request that has been made is to not wear fancy dress which could be seen as garish.’

Rely on layers to beat the weather

The forecast is distinctly patchy for Cheltenham this week, and even if it weren’t you can’t rely on clear skies.  ‘Fortunately there are many ways to dress chic and keep your look practical,’ says Charlie. ‘Layering pieces such as capes, hats and gloves can provide some protection from the elements whilst still adhering to an elevated attire.

As for footwear? Clearly on wet grass any sort of heels are out, but Charlie recommends an alternative: ‘Boots with lower block heels are your best friend for these events and will carry you through with ease. Avoid any performance footwear and stick to quintessentially county silhouettes for your boot choices and you can’t go wrong.’