Introducing

Racing Legends

Racing Legends is a portrait series honouring racing’s sporting heroes - not as we know them, but as they’ve never been seen before. From Jockeys to pundits, this campaign embodies the racing culture etched into Cheltenham's history.

In The Spotlight

Harry Cobden

Harry Cobden is one of Britain’s leading National Hunt jockeys and a cornerstone of Paul Nicholls’ champion yard at Ditcheat. Raised in Somerset in a racing family, he rode his first winner as a teenager and quickly rose through the ranks, becoming Champion Conditional Jockey in 2017. A familiar face at Cheltenham, Harry has enjoyed multiple top-level victories at the Festival, cementing his reputation on racing’s biggest stage. Just as the racing is central to Cheltenham, so too is the style on course. As a Holland Cooper brand ambassador, he perfectly represents the meeting’s blend of heritage, performance and race day elegance.

Find Out More

A celebration of heritage design

The Cheltenham Festival 2026

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'In professional sport, especially racing, it’s as much a mental game as a physical one.'


- Harry Cobden

“Biggest crowds. Biggest pressure. Expectation - winning at Cheltenham gets covered over whatever else you’ve done.


- Ruby Walsh

Explore The

Racing Legends Collection

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“It means a lot to wear British-made tailoring at Cheltenham. It’s quintessentially British - and that’s important.”


- Ed Chamberlin

A celebration of heritage design

The Cheltenham Festival 2026

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Behind The Scenes

Visit us at Cheltenham Festival

We have two stands at Cheltenham this year where we would be delighted to welcome you, so please do come and visit us. In a new location for 2026, the Orchard Boutique is a curated replica of our flagship boutique, presenting elevated tailoring and key collections. Stand 32 in the Shopping Village, is a bespoke stand where we will be showcasing our best-selling pieces and refined finishing accessories.