Tweed, bouclé and fascinators optional: The complicated unwritten rules of Cheltenham festival fashion

There’s no official dress code, but that doesn’t make dressing for Cheltenham races any easier. Katie Rosseinsky asks the experts for their advice on how to make a statement (in a good way)

Race-day style: Zara Tindall often opts for an eye-catching headpiece – but that’s not essential (PA)

Do women have to wear a fascinator? Do men need to dress like they’re attending a shooting party hosted by Julian Fellowes? Is tweed essential? And what if it chucks it down? Think of Cheltenham races, which starts today (12 March), and you’ll probably picture, well, all of the above: a sea of countrified herringbones and checks, fur collars and more fedoras than a pick-up artist convention, probably adorned with pheasant feathers.

But while other equestrian events have always tended to enforce strict, often specific dress codes, Cheltenham has never actually had an official policy on race day attire. The expectation that ticket holders would dress smartly was just one of the unwritten rules that are so common in posh-skewing events, especially those involving horses. Last year, though, things loosened up a bit. The Jockey Club (that’s the organisation that owns 15 of Britain’s most famous racecourses – the likes of Aintree, Epsom, Sandown and Cheltenham, but not Ascot, the proud enforcer of British horse racing’s most Byzantine dress code) scrapped edicts about dress across all of its venues. The only exception, they said, would be “offensive fancy dress, offensive clothing of any kind and replica sports shirts”.

This move was part of an attempt to overhaul racing’s reputation, in order to make it feel more “accessible and inclusive”. According to Jockey Club chief executive Nevin Truesdale, “enforcing a dress code seems rather outdated in the 21st century in the eyes of many of our racegoers”. Now, attendees at all of the organisation’s events are simply encouraged to “dress as you feel most comfortable and confident” – which is all very well and good, but certainly leaves a lot of room for manoeuvre. It’s a bit like the sartorial equivalent of when your mum tells you she “doesn’t really need anything” for her birthday: vague and full of potential pitfalls. And, we should note, not everyone is thrilled by this slight shake-up. “It’s a dreadful idea because it encourages mediocrity,” milliner Jonny Beardsall told The Times ahead of last year’s races.

Reports from the 2023 event did pick out a few more pairs of jeans and trainers and even – brace yourselves – tracksuits than we might have expected in previous years. But there’s no real cause for Cheltenham diehards to be wringing their elegantly gloved hands. “I’m yet to notice much difference in the outfits that guests are choosing to wear,” says personal stylist Lindsay Edwards. “It seems that the vast majority of people remain keen to ‘dress up for the races.’” This year, Ladies’ Day has been rebranded as “Style Wednesday”, and is all about slow fashion, celebrating vintage, borrowed items and heirloom pieces (rental platforms might be your new best friend when it comes to nailing this particular theme).

So how to go about planning what to wear? Every Cheltenham outfit should start with a glance at the weather forecast, so you know what you’re dealing with. “Fabric wise, wool, tweed and bouclé work particularly well in poor weather conditions,” Edwards advises, “as does bonded cotton that has water-repelling qualities”. She also advises packing a transparent umbrella (it’s what Queen Elizabeth used to do, allowing her to see and be seen). If it’s chilly, a jumpsuit might be a good option, suggests Susie Hasler, personal stylist at Styled by Susie, because “you could even get away with tights underneath if you really feel the cold”. Or, if you’re a bit more daring, “you could even look at a co-ord trouser suit in a warm fabric such as velvet”, she says. Think Claudia Winkleman striding around a Scottish castle in The Traitors.

You also need to think about the overall effect. If you’re going to be standing around outside all day, “it’s likely that your outfit won’t be fully seen in its entirety”, Hasler cautions, “so rather than chuck on a last minute rain jacket, look for something warm and glamorous.” Otherwise your overall vibe might end up more football manager grimacing from the dugout than chic racegoer. She advises opting for longer styles in fleecy teddy, faux fur or smart felt. And as for shoes? “Be mindful that if you’re wearing heels that are uncomfortable at the beginning of the day, by the end of the races, you’ll want to kick them off,” Masler wisely notes. Stilettos are a bad idea, unless you fancy trailing behind your friends as you attempt to pull your spindly heels out of the mud every few steps. “If you go for a heel, ensure it has a sturdy block heel so you don’t sink into the grass,” advises Louise Duncum, personal stylist at Weiz Styles. “A platform sole is also a great option to give height but more comfort on your foot.”

Fashion-forward: designer Jade Holland Cooper wears an eye-catching trouser suit (Andrew Matthews/PA Wire)

When it comes to picking a colour, Lindsay Edwards reckons that for men, “a well-cut suit in country colours such as olive green or brown looks great, as well as checkered or herringbone tweed”. And for women racegoers seeking something similarly understated, she advises trying “navy, plum or olive green. If you’re unsure what colours suit you, try teal or a Cadbury’s purple, which work for everyone, whatever their colouring”. White or cream, she says, probably aren’t the best choice, as they “will show up any unavoidable splashes of mud throughout the day”. It’s early spring in Gloucestershire, after all, not summer on the Riviera.

Essentially, you don’t need to aim for full-on lord or lady of the manor cosplay, or go for something trend-led. “The most stylish attendees on the day will be those who opt for timeless classics mixed with a few on-trend elements to achieve a balanced and sophisticated look,” says Alison Lowe, fashion consultant and course leader in MBA Fashion Entrepreneurship at the University of East London. And no, you really don’t need to wear a fascinator if that’s your own personal form of sartorial hell (just me?)

“Cheltenham is not the occasion for wildly elaborate headwear,” Lowe adds. “Save those overly extravagant headpieces for Ascot.” Noted.