What to Wear: Chester Races

When you’re attending the oldest racecourse in the world, you need an outfit worthy of the occasion. Established in 1539 and featuring historic races such as the Chester Cup and the Cheshire Oaks, Chester racecourse attracts over 300,000 visitors each year. If you’re lucky enough to be attending this year, get ready for a spectacular event that’s renowned not only for its racing, but for its class and style.

The Chester Races Dress Code

The Boodles May Festival runs from the 7th-9th May 2025, and dressing smart is encouraged, especially in the more formal areas such as the County Long Room or the Winning Post. The County Concourse and Tattersalls Enclosure generally offer a more smart-casual vibe, but you’ll definitely want to look your best for the May Festival - the official dress code asks for a jacket, collared shirt and tie for the smarter areas, and a collared shirt and smart trousers or jeans for the Tattersalls.

Whether you’re enjoying the spectacle from the County Concourse or a luxurious private box, here are this season’s best looks for a stylish and confident day at this prestigious event in the racing calendar.

What to Wear To Chester Races

The Blazer and Chinos Combo

This May, one of the most popular styles making the rounds is the relaxed blazer and chinos look and is perfect for the Tattersalls enclosure. It’s smart but not stuffy and perfect if you want something that sits somewhere between traditional tailoring and smart casual.

A navy blazer works brilliantly here, paired with stone or light beige chinos. We love a crisp white Oxford shirt to bring the look together, while loafers or tan brogues are a safe bet that will keep you comfy but sharp. Add a patterned pocket square for a pop of colour, your favourite watch, a pair of sunglasses - and you’re good to go. Leave your collar open if it’s a warm day, or dress it up with a tie if that’s your thing.

The Pastel Two Piece

Suiting up? For the majority of the enclosures at the May festival, a suit is a must. We’re on the cusp of summer, so Chester Races is the perfect time to ditch the navy and dark grey. Soft pastel suits are part of this season’s freshest colourways, so opt for cloud blue, rose pink or pale grey in a lightweight linen blend. Match your suit to your shirt or stick to the classic white. Try a knitted tie or subtle lapel pin to add a splash of personality to your finished look. Smart brown shoes are a pastel shade’s best friend, so opt for chocolate leather Oxfords or a suede loafer.

Relaxed Neutrals

Neutrals are big this summer, and one of the easiest ways to look stylish with minimal effort. If you’re in a more casual enclosure like The Roodee or even The Tattersalls outside of the May festival but still want to look put-together for drinks in the sun with your mates, opt for a t-shirt in white or pastel pink and pair chinos in a neutral shade like stone or beige. A neutral blazer like the linen-blend in oatmeal or a light shacket pretty much goes with anything and is a good investment for the coming summer months if you don’t have this smart casual staple in your wardrobe already. Wear with your best white trainers or suede loafers.

The Statement Trouser

Try flipping the usual formula and letting windowpane checks or tweed trousers do the talking with a simple navy blazer and an open-collar white shirt, keeping the top half clean to balance things out. Lean into the vintage feel of this outfit with a flat cap or matching waistcoat - you could even add a pocket watch if you’re feeling Peaky Blinders-esque. Don’t forget, the bottom button of your waistcoat always stays undone.

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