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Cheltenham guests are all about the check suits - here’s how to get the look

From Zara Tindall to Jade Holland Cooper, guests are flying the flag for checked tailoring

cheltenham check suits
Lauren Ramsay
Online Writer
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Cheltenham Festival never fails to deliver the hottest country-chic trends of the moment. Celebrities, racing fans and royals alike step out and serve some serious looks over four days in the quaint county of Gloucestershire, and this year is no exception.

The number one rule for Chelteham dressing is "dress for the weather, and also be comfortable”, according to races style muse Jade Holland Cooper. But that doesn’t mean a compromise on style. The founder of British countryside-inspired label Holland Cooper told Hello! Fashion that the biggest Cheltenham fashion faux pas is "not wearing layers”.

MORE: The ultimate Cheltenham races 2023 style guide with Jade Holland Cooper

RELATED: Cheltenham 2023: The best dressed guests at the races so far

“Layers are so important,” Jade explained. “Thermal vests under everything that you’re wearing is a must to ensure you enjoy the day."

And sophisticated layering is exactly what sensibly stylish guests did – tonal polo necks under jackets, 2022’s waistcoat trend elevated as an extra layer of warmth, and of course silk scarves were everywhere. Though we noticed many-a-trend over the week – think oversized fur cuffs and perfectly coordinated headpieces – there was an undeniable number of guests donning super chic, check suits.

Jade Holland Cooper herself wore checks across all four days, whilst Princess Anne’s daughter Zara Tindall, singer Laura Wright and racing TV presenter Rosie Tapner also sported chequered suits in various fits and colourways. 

The best thing about investing in separates is that they can be worn…separately, meaning the cost-per-wear value is certainly worth it. In the summer swap out your jacket for a crisp white t-shirt, or wear the chequered jacket over a skirt with flat shoes. Now is the perfect time to invest:


As0s brown suit

NA-KD X Georgina Lennon co-ord tailored trousers in brown check, £45, ASOS


NA-KD X Georgina Lennon co-ord tailored blazer in brown check, £75, ASOS


Asos green sui

Mix and Match grandad jacket and trousers in green, £104, ASOS

Twisted tartan

Green and Navy tartan trousers, £70, Twisted Tartan


Green and Navy tartan jacket, £150, Twisted Tartan




Checked flared trousers, £99, Cos


Checked double-breasted blazer, £190, Cos



Wide Leg Flared Check Trousers, £130, Boden


Brighton check jacket, £190, Boden


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