Cheltenham Festival – Our style guide for race day

Jump Season - A Classic of British Style and Heritage

Introducing: The 250th Anniversary Canterbury Trilby Reading Jump Season - A Classic of British Style and Heritage 4 minutes Next Race Day Style - Felts

Steeped in equine heritage, The Cheltenham Festival (12.3 to 15.3) heralds the start of the racing season, making it one of the must-attend events in the sporting calendar. Offering a stage for top-tier jockeys to vie against each other, the four-day jumps event also serves as a joyous gathering fit for congenial socialising (though it's immensely raucous for some, given its coincidence with St Patrick's Day) and, perhaps most importantly, an occasion to dress up in country-inspired clothing, naturally finished with a Christys' felt hat or woollen cap.

Jockey riding horse
Jockeys riding in front of crowd

If there were one minuscule issue with Cheltenham, it would be how nuanced the dress code, or lack thereof, is. Instead of being specific like Royal Ascot, you’re encouraged ‘to dress to feel your best,’ which can be interpreted in many ways. “Thankfully, spectators still respect the traditions and sense of occasion by dressing in tweed and country clothing that helps create the unique Cheltenham atmosphere," says Chris Modoo, a classic menswear authority and oracle for occasion wear. This unique atmosphere has much to do with the sea of elegant and sophisticated headwear.

March can throw up some unexpected weather, so raincoats, rubber-soled shoes and sensible headwear are advised, particularly felted hats, which have been referred to over the years as 'racing felts'. The wide brim provides your face with a considerable degree of protection, whilst the felt is naturally water-repellent. We have options for both men and women in wool, rabbit and beaver, with the latter being our pick due to the optimal combination of lightness, density and luxurious handle.

For men, a Trilby or Fedora can be a finishing touch to a standard three-piece tweed suit. However, it's just as helpful in elevating more casual outfits. For example, a pair of Goodyear-welted shoes, charcoal flannel trousers, earthy-toned cashmere knitwear and an all-weather-conquering olive waxed jacket. Such a combination "will instantly elevate your look from a trip down the pub to Cheltenham-ready," says Modoo.

Three Christys' fedoras on a Land Rover
A man talking on a phone and wearing a black Christys' fedora
A man holding a brown Christys' fedora

For women, a statement hat perfectly proportioned and accented with a delicate dove feather is a must-have accessory at Cheltenham. "Trilby and Fedora style hats can be extremely feminine and will complement both structured tailoring and flowing dresses," says Jemima Wilson, a luxury journalist and equine enthusiast. This year, Wilson plans on wearing a coat made from a cream boucle fabric with hints of brown and red, which would be perfect for pairing with one of our brown or burgundy felt Fedora hats.

A woman holding a brown Christys' fedora
A woman looking at a horse in a field
A woman wearing a green Christys' Crushable Safari hat

When it comes to wearing our 8-piece and Balmoral caps at Cheltenham this season, there's more room for interpretation and experimentation due to their inherently casual nature. That said, there should be some cautionary measures put in place. "Tweed caps can be worn with tailoring but try to avoid looking like you're an extra in Peaky Blinders by matching your cap with your suit – save that for Goodwood Revival," says Modoo.

One of the advantages of wearing tweed is that it’s more versatile than you think, this is due to the myriad of colours nestled within the fabric. When less dominant tones are picked out and matched with your outfit, it’s often incredibly tasteful and stylish. Moreover, it doesn’t look like you have tried to achieve that.

Despite the cap’s casual personality, they can also achieve what Wilson describes as “sophisticated nonchalance”, particularly when “worn with a pair of beautifully-cut high-waisted tapered trousers worn with ankle boots, a ruffle detail shirt or a roll neck, and a blazer belted at the waist for a more hourglass shape.”

A man in a field wearing a Christys' 8 Piece Baker Boy Tweed Cap
A man leaning on a Land Rover and wearing a Christys' 8 Piece Baker Boy Tweed Cap
A man in a field wearing a Christys' Harris Tweed Balmoral Flat Cap
A woman in a field wearing a Christys' 8 Piece Baker Boy Tweed Cap

If you are attending this year for the first time and need inspiration, Wilson suggests looking at some vintage Ralph Lauren womenswear ads, which combine heritage fabrics with a modern sensibility drawn from timeless dress codes. “It’s where I get a lot of my country-style inspiration from,” she says. Of course, HRH The King is also an endless source of inspiration and a leading example in showing the rewards of investing in high-quality clothing.

A parting lesson to finish with from Modoo is that “the best-dressed attendees at The Cheltenham Festival combine the old with the new, so it's better to wear your new Christys' hat with a trusty old tweed suit, country-checked waistcoat and vintage overcoat."

Leave a comment

All comments are moderated before being published.

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.