A Legacy of Style
Since its founding in 1539, when the Mayor of Chester, Henry Gee, introduced an annual race meeting on the Roodee - presenting the owners of horses with silver bells – Chester Races has evolved into the definitive stage for the region’s most stylish guests.
This year, style is just as important as the racing and Chester Racecourse has once again partnered with Cheshire Oaks Designer Outlet to help guests perfect their raceday look. Guests are encouraged to dress for the special occasion and most importantly to feel confident and comfortable in whatever they choose to wear. Each enclosure has a specific dress code; full details alongside style inspiration and guidelines to help select the perfect race day outfit can be found at chester-races.com.
Beki Gregory, Senior Stylist at Cheshire Oaks Designer Outlet, said: “Spring Summer 2026 is all about confident expression through contrast and personality. I’m loving the power of monochrome, especially when paired with sharp tailoring or fluid silhouettes for a polished, modern look.
“Vintage-inspired styles are also making a strong comeback, with designers balancing nostalgic charm and contemporary styling. Think delicate floral prints and silhouettes that evoke timeless elegance.
For those wanting to stand out, vibrant rainbow hues are taking centre stage, bringing energy and individuality to any outfit.
“My top tips for this year’s Ladies Day would be to choose a statement accessory to elevate your look, stick to one standout trend rather than mixing all three, and prioritise comfort with chic yet practical footwear... you’ll be on your feet more than you think!”
Kenny Murray, General Manager at Cheshire Oaks Designer Outlet, said: “We’re delighted to once again be the official style partners of the Boodles May Festival at Chester Racecourse.
“The fixture is a staple and one of the most highly anticipated at the racecourse, with plenty of colour, glamour and style on show, especially on Ladies Day.
“As the home of more than 140 brands, located less than 20 minutes away from the racecourse, we offer so much fashion inspiration for the occasion, as well as the opportunity to save up to 60% off RRP on a fabulous range of designer brands.”
Best Dressed Competition
Racegoers battle it out in the style stakes on Ladies Day on 7th May to be crowned the ‘Best Dressed’ guest in Chester Races’ renowned style competition. Don a fancy flowing dress or a suave smart suit and be crowned Chester’s most glamorous guest. Judges often favour unique outfits over generic looks, so think outside the box. Think chic and accessorise with a bespoke hat or fascinator and a matching handbag.
Prizes Include:
1st Place
Boodles Necklace
Cheshire Oaks £500 Voucher
American Holidays - £500 holiday voucher
Ladbrokes - £100 free bet on the day
The Cheshire Magazine Subscription
Chester Racecourse Hospitality
Flowers provided by The Cheshire Magazine
Chester Racecourse Champagne
2nd Place
Cheshire Oaks £250 Voucher
The Cheshire Magazine Subscription
Chester Racecourse Hospitality
Flowers provided by The Cheshire Magazine
Chester Racecourse Champagne
3rd Place
Cheshire Oaks £100 Voucher
The Cheshire Magazine Subscription
Chester Racecourse Hospitality
Flowers provided by The Cheshire Magazine
Chester Racecourse Champagne
Book your tickets at chester-races.com
Hungry for more?
Read up on the latest news, delicious eats, travel treats and seasonal style trends in FEATURES, or browse a curated selection of our FEATURED PRODUCTS, meander through our guide to the finest things to do in Cheshire and beyond in WHATS ON or partake in our COMPETITIONS.
About The CHESHIRE Magazine
We are the definitive guide to luxury lifestyle in the North West. Latest news, delicious eats, travel treats and seasonal style trends. The Cheshire Magazine is the largest luxury lifestyle title for the North West of England, dropping directly through the letterboxes of VIP subscribers from the Wirral to Greater Manchester plus all the villages and towns in between and digitally available as a subscription in print and digital on issuu.com worldwide. We specialise in connecting luxury brands to likeminded consumers.
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