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

Nico de Boinville

Nico de Boinville is one of Britain’s top National Hunt jockeys, celebrated for his skill, tactical nous, and partnerships with some of the sport’s leading horses. A key rider for trainer Nicky Henderson, Nico has enjoyed multiple Grade 1 successes and memorable wins at the Cheltenham Festival. He knows what makes the Festival truly special, saying, “The atmosphere at Cheltenham Festival is unlike anything I’ve ever encountered.” His presence at the meeting reflects both the excitement of top-level racing and the prestige of the event, perfectly aligning with Holland Cooper’s blend of performance, heritage, and modern British style.

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.