Located in the heart of the historic city of Chester, this racecourse known as the Roodee is the oldest racecourse still in use in the UK, if not the world! It is one of the most prestigious Flat racecourses in the country with racing events running from May to September and is also the smallest racecourse. Chester Racecourse’s most famous and popular event is the three day May Festival which kicks off their season with style. Boodles May Festival starts Wednesday 6th May until Friday 8th May 2026. Ladies Day is on Thursday 7th May where you’ll have the chance to be crowned the most stylish attendee in their Best Dressed Competition (yes it is open to the gents too) , going home with prizes that would make anyone envious!

Official Dress Code For County Concourse Enclosure,County Long Room, Winning Post Enclosure and The Garden plus the Hospitality Areas and Chester Members.

For the Hospitality Areas and Chester Members, gentlemen are required to wear a jacket, smart trousers, collared shirt and tie. For the County Concourse Enclosure, County Long Room, Winning Post Enclosure and the Garden, gentlemen are required to wear a jacket and collared shirt.  Allowed in these areas: Well-tailored suit, Well-tailored blazer, Smart trousers, A collared shirt , Tie  Not allowed in these areas: Jeans, Trainers, Shorts, Tracksuits, T-shirts, Sportswear , Fancy Dress & Inappropriate clothing.

All prices are correct at time of publishing

A sharp well tailored suit is the sartorial choice for many dapper gents at this race. For timeless style: Brunello Cucinelli Chevron blazer in a soft hazelnut brown chevron weave of linen and virgin wool fabric. The blazer has a one and half breasted shallow wrap rather than a full double breasted style and so can be worn open. £3500.00 Matching Chevron trousers features double pleats for volume, turnups and a high waist. £1000.00 Wear the trousers with their Leather braided pattern belt in chocolate brown. £600.00 The suit is styled here with their navy blue Jersey shirt in a linen/cotton blend with a spread collar. £830.00 but would also look perfect with their classic Poplin shirt in apricot £580.00.  A tie is required for the hospitality area and Chester members and completes the sartorial look Silk tie with squares pattern in brown £240.00 Add a silk pocket square Silk pocket square in Navy Blue £210.00 plus other colours available. Slip on a pair of Brunello Cucinelli’s Calfskin penny loafers in rust brown with braided leather apron £1000.00. Accessorise with their Rectangular acetate sunglasses in Havana and creamy Panama shade along the arms emulating the play of light and shadow at sunset. £514.00 Finish off with jewellery: Tateossian London’s Constellation Beaded Bracelet with rhodium-plated sterling silver discs and hand carved tiger eye rondelle beads £775.00 plus their Calas Flower Pin made from tiger eye stone hand carved to resemble a violet flower with palladium plated base metal. £180.00

Official Dress Code for Tattersalls Enclosure.

Chester racecourse say “We’re looking for a smart-casual vibe. Picture yourself in a chic ensemble, such as a polo shirt paired with smart chinos.” Gents are required to wear a collared shirt and smart trousers/jeans. Allowed in Tattersalls:  Polo Shirt, Collared shirt, Smart Jeans (not ripped), Smart Trousers, Chinos, smart non branded trainers ,Not allowed in Tattersalls: Trainers, Shorts , Tracksuits , T-shirts, Sportswear, Fancy Dress or Inappropriate clothing.

We’ve chosen a cool cotton blend  GUESS® Polo sweater with short sleeves in classic beige. £75.00. Teamed with GUESS® Linen-blend slim pants in cream. £95.00 and GUESS® Bucharest 4G logo belt which is also reversible. £55.00. A jacket is not required but if the weather warrants it GUESS® Single breasted blazer in cream is the perfect match for the slim pants £125.00. Go for a pair of GUESS® Opperne Moccasin in brown suede £115.00. These allow the wearer to go sockless for a relaxed formal style. Whether dull or sunny, look cool in a pair of their Square sunglasses in dark brown £90.00. A must have for the modern man is the bracelet, ranging from simple leather straps or metal bangles to colourful chunky beads, from the high street to designer labels. Stack this arm candy with GUESS® Mare Magnum bracelet in a twist of brown and blue £80.00 and a caramel coloured GUESS® Mare Magnum bracelet £80.00 with other colours available. Finish off that continental style look with their Milano smart mini crossbody to carry your racing essentials £65.00.

Dress Code for The Roodee  

The Roodee is more of a relaxed environment, but Chestrer Racecourse say “Don’t let that stop you from donning your best outfit for a grand day out at the races. Dress it up or dress it down – it’s up to you. All that we ask is that you don’t wear offensive clothing or offensive fancy dress as these are not allowed.” Allowed in the Roodee:Relaxed clothing , Fancy dress , Sports clothing , Trainers Not allowed in the Roodee: Offensive clothing , Offensive fancy dress.

We’ve chosen Rise & Fall’s Organic Cotton Straight Leg 5-Pocket Chino  in a silt shade of brown. £135.00 with their Classic Cotton Crew Neck T-shirt in a parchment shade of white. £40.00. Teamed with their brown Suede Leather Silver Buckle Belt in brown £80.00 and their Denim Overshirt £130.00. Keep the sun or rain off your head with Lacoste’s Embroidered Crocodile Petit Piqué Beret in midnight blue £70.00 Add a fun and a pop of colour to your outfit with their Active Line Rectangle Sunglasses in matte blue £120.00. Accessorise with Completed Works’ Tidelands – Tiger Eye and Recycled Gold Vermeil Bracelet £165.00 and Tidelands – Tiger Eye and Recycled Gold Vermeil Necklace £285.00. Branded Trainers are acceptable in The Roodee so we’ve chosen Lacoste’s Elite Active Sneakers in dark brown £130.00. Please note there is limited cover in the Dee Stand and no cover in the Open Course so be prepared and check the weather beforehand. British weather is unpredictable and the day’s forecast could be rain plus sunny spells so taking a small rucksack such as Lacoste’s  Classic Backpack would be a safe bet. £150.00 This way you can pop in an umbrella for the rain, a sweatshirt if it gets chilly and suntan lotion when the sun starts to shine. 

Brunello Cucinelli images courtesy of pr Agency LM Communications

Tateossian London images courtesy of pr agency Task PR

Rise & Fall, Completed Works and Lacoste images courtesy of pr agency Purple PR

Guess images provided by pr agency Trace Publicity

Background shot of Chester Racecourse provided by Canva.com