Cheltenham Fashion Guide 2025
The year of Tailored Tweeds and Suited Looks: The Ultimate Guide for what to wear to Cheltenham
About Clare Haggas: Clare is a renowned wildlife artist, based in Cheltenham England, who brings her artwork to life on British made, silk accessories. Read more here.
Cheltenham Festival is not just a highlight of the racing calendar but also a key moment in the style stakes.
Combining tradition with contemporary fashion, 2025 will be the year of tailored tweed, sophisticated suits, and shining silks. Whether you’re embracing classic equestrian style or looking for a bold twist, here's our run down of the key fashion trends this year:
Effortless Co-Ords
For a cohesive and chic look, let coordinated silk accessories do the talking, like the Caledonia Holly Berry Red Classic Scarf with the matching scrunchie.
As seen on influencer Alix Jade Selby @alix_jade during the November Meeting at Cheltenham, this combination truly shines against tailored tweed. It’s a simple yet stylish way to add colour and sophistication to your race day outfit.
Effortless Co-Ords
For a cohesive and chic look, let coordinated silk accessories do the talking, like the Caledonia Holly Berry Red Classic Scarf with the matching scrunchie.
As seen on influencer Alix Jade Selby @alix_jade during the November Meeting at Cheltenham, this combination truly shines against tailored tweed. It’s a simple yet stylish way to add colour and sophistication to your race day outfit.
Modern Heritage
Embrace tradition with a modern twist, follow @hemsleysam’s lead by pairing a long trench & coordinating shorts with Clare’s Navy Large Square Caledonia tartan Silk Scarf.
Black accessories complete this sophisticated look, with a nod to heritage, but with a contemporary edge. It’s a confident and stylish choice for those who want to stand out.
Modern Heritage
Embrace tradition with a modern twist, follow @hemsleysam’s lead by pairing a long trench & coordinating shorts with Clare’s Navy Large Square Caledonia tartan Silk Scarf.
Black accessories complete this sophisticated look, with a nod to heritage, but with a contemporary edge. It’s a confident and stylish choice for those who want to stand out.
Equestrian Elegance
Nail the classic equestrian look by pairing the large square Heads or Tails scarf in khaki with a crisp white shirt, as styled by @amytowne. This outfit is quintessentially British and perfect for embracing Cheltenham's racing heritage.
Add some leather boots to complete the look.
Equestrian Elegance
Nail the classic equestrian look by pairing the large square Heads or Tails scarf in khaki with a crisp white shirt, as styled by @amytowne. This outfit is quintessentially British and perfect for embracing Cheltenham's racing heritage.
Add some leather boots to complete the look.
Timeless Tradition
For a classic equestrian-inspired look, Clare Haggas’ ‘Hold Your Horses’ scarf is the ultimate accessory.
As showcased by @townlifecountrystyle, this one of Clare's most versatile scarves, in staple Navy - a colour that suits all skin tones. And it's perfect for those who want to embody the spirit of the races.
Timeless Tradition
For a classic equestrian-inspired look, Clare Haggas’ ‘Hold Your Horses’ scarf is the ultimate accessory.
As showcased by @townlifecountrystyle, this one of Clare's most versatile scarves, in staple Navy - a colour that suits all skin tones. And it's perfect for those who want to embody the spirit of the races.
For The Bold
If you’re looking to make a statement, the Turf War black and gold long kimono is the perfect choice.
This standout piece, worn by @lady_lisa_luxe at the 2024 Cheltenham Festival, garnered attention both in the press and on TV. Why not style it with slim trousers and understated accessories to create a bold yet balanced race day look.
For The Bold
If you’re looking to make a statement, the Turf War black and gold long kimono is the perfect choice.
This standout piece, worn by @lady_lisa_luxe at the 2024 Cheltenham Festival, garnered attention both in the press and on TV. Why not style it with slim trousers and understated accessories to create a bold yet balanced race day look.
Chic Comfort
Stay warm and stylish with a fur-trimmed gilet, an ideal layering piece for the unpredictable March weather.
Take inspiration from @weather_with_helena, who paired hers with chocolate brown accessories and the stunning Moss Green Caledonia Silk Twilly (or ribbon scarf). This look combines practicality with style, making it perfect for race day.
Chic Comfort
Stay warm and stylish with a fur-trimmed gilet, an ideal layering piece for the unpredictable March weather.
Take inspiration from @weather_with_helena, who paired hers with chocolate brown accessories and the stunning Moss Green Caledonia Silk Twilly (or ribbon scarf). This look combines practicality with style, making it perfect for race day.
Image credit: @mary_jane_braunton featuring the Large Square Toffee Heads Or Tails Silk Scarf
Image credit: @hemsleysam with some very fashionable ladies! Featuring Large Square Teal and Rust Rearing To Go Silk Scarf and Classic Toffee and Navy Best in Show (currently out of stock)
Image credit: @ginneyymills with her Narrow Navy Heads or Tails Silk Scarf tied to a handbag
Image credit: @alix_jade in 2 Classic Forest Green Walk On The Wild Side Silk Scarves
Image credit: @sheenamurphy_2143 in the Classic Oyster & Teal Rearing To Go Silk Scarf
Image credit: @hemsleysam in 2 Large Square Turf War Duck Egg Silk Scarves
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