'Do not be afraid of looking like a tweed factory has thrown up on you': A snob’s guide to what to wear for Cheltenham

Nine fail-safe tips for looking your best at Cheltenham Festival 2026.

Zara Tindall, Dolly Maude and Natalie Pinkham
Zara Tindall, Dolly Maude and Natalie Pinkham on day one of the 2023 Cheltenham Festival.
(Image credit: Alamy)

And we’re off. Nearly. Cheltenham is almost upon us. But what to wear? It’s not Royal Ascot, but it’s still quite the week and you don’t want to embarrass yourself in the Guinness Tent.

Here are a few (clothing) tips. For horse tips you’ll have to ask someone else.

  1. Think warmth. It’s March. Wind whips around that racecourse like a tornado. Thermals are your friend. ‘Thermal tights over thermal knickers,’ advises Georgia Toffolo, who says Cheltenham is her favourite week of the year and takes dressing for it with due seriousness. ‘And disposable hand and feet warmers, like you use for skiing'
  2. You don’t want bare limbs. See above. There will be women in tiny miniskirts, but they may regret this sartorial decision by the first race
  3. Skirt suits, on the other hand, are dead chic. ‘I love a skirt suit,’ says Isabel Spearman, ‘and will probably wear a beloved Cefinn (now closed, but available to shop second hand) one in a beautiful blue — it feels modern and (importantly) comfortable'
  4. Tweed. Do not be afraid of looking like a tweed factory has thrown up on you. Tweed coat, tweed trousers, tweed waistcoat and so on. The Cheltenham look, in recent years, has become Peaky Blinders (those baker boy hats) meets Toad of Toad Hall. You will blend in wearing almost any form of tweed
  5. And/or, look to the brand Holland Cooper. Its eponymous founder, Jade, is another who takes dressing for this week with due care and attention, and her label features long trench coats, trousers, and warm jerseys with gold button detailing that makes them look a bit more upmarket than your average jersey, all of which would work in the paddock
  6. Very bright colours are more Ascot. The colour scheme for Cheltenham is mud, really. Think browns and beiges or more muted colours if you don’t want to stick out
  7.  Hats. I like a brown trilby, which can look especially dashing on women. Very handy to hide under if it’s raining, and it means you’ll worry less about your hair. Mine came from Oliver Brown, but Holland Cooper do them too. Or, says Georgia, buy a faux-fur bucket hat for a fiver from eBay. ‘Very Camilla-esque,’ she says approvingly, in reference to the Queen. Although she adds that Princess Anne is a good source of fashion inspiration for this week — think thick woollen overcoats, scarves, suede boots
  8. Ideally flat shoes or block heels only. You’ll spend a lot of time on your feet, probably hurrying between the paddock, the bookies, and the grandstand. If you’re very posh, you may be in a box, or the Turf, but you’ll still probably want to escape a couple of times and mingle with the masses. This is not the moment for stilettos
  9. Don’t panic, you’ll be quite safe in Granny’s fur. Nobody’s going to lob a bucket of paint on your mink stole at Cheltenham
Sophia Money-Coutts

Sophia Money-Coutts is a freelance features writer and author; she was previously the Features Director at Tatler and appeared on the Country Life Frontispiece in 2022. She has written for The Standard, The Sunday Telegraph and The Times and has six books to her name.