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OVER £10,000 WORTH OF PRIZES TO BE WON
Ladies Day is a celebration of the glamour and glory of the Cheltenham Festival.
On the track, the feature race of the day is the BetMGM Queen Mother Champion Chase, where speed, accuracy and precision is the key.
However off the track, for many racegoers, the Cheltenham Festival is chance to step into the spotlight and celebrate raceday style.
Our Best Dressed competition gives racegoers the opportunity to showcase their best looks and be in with a chance of winning some fantastic prizes.
CHELTENHAM FESTIVAL BEST DRESSED 2026
This year, raceday style is celebrated across three categories
Best Dressed - for effortless elegance that stands out on its own.
Best Dressed Duo - celebrating perfectly paired raceday style.
Best Dressed Group - the best looks, even better together.
ENTRY IS AS EASY AS 1,2,3
1. Have your photograph taken against any of our three backdrops (located in The Plaza, The Centaur and The Best Mate Enclosure)
2. Scan the QR code next to the backdrop
3. Submit your name, contact details and your photograph.
Entries can only be made on course - entries must be submitted by 14:30, with category winners presented following the feature race at 16:00.
Boodles was established over two centuries ago and enjoys an illustrious reputation based on innovative design and quality craftsmanship. The family-run fine jewellery house specialises in diamonds and precious gemstones and epitomises the best of British design. Classic and contemporary all at once, Boodles offers everything within the fine jewellery universe, from beautifully crafted engagement rings to wonderful one-of-a-kind collections.
Steeped in history and boasting 90 acres of glorious grounds, Ellenborough Park is nestled between the Cotswolds' highest point and the gallops of Cheltenham Racecourse. Our sumptuous manor house has been lovingly restored to its original five-star glory and is now home to laid-back dining experiences, a soul-soothing spa and rooms brimming with country house character.
Holland Cooper is known for its refined blend of timeless elegance and contemporary style, from tailored outerwear to chic accessories, each piece is crafted with attention to detail and a commitment to exceptional craftsmanship. Combining classic design with modern sophistication, Holland Cooper is go-to for those seeking stylish, luxurious, and enduring pieces that elevate any wardrobe.
Debenhams offer a thoughtfully curated collection of fashion, beauty, and home products, blending style, quality, and value. With a focus on delivering the latest trends alongside timeless pieces, you can enjoy a seamless and enjoyable shopping experience, with access to beautifully crafted items that suit every lifestyle.
THE BEST DRESSED COMPETITION 2026 - PRIZE LIST
Best Dressed racegoer prizes
Best Dressed duo prizes
Best Dressed group prizes
Up to 6 x BetFred Derby Festival 2026 tickets – Grandstand Enclosure, Ladies Day (Friday 5th June 2026)
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After gracing the front cover of Vogue at the age of 16, Rosie modelled for 10 years before turning her attention to presenting in the world of racing and equestrian sports. Rosie is known for her engaging interview style, her ‘can do’ attitude and her magnetic yet down-to-earth demeanour.
Ellie Evelyn Smith is a London-based presenter known for her energy, sharp wit, and keen eye for style. Bringing charisma and confidence to everything she hosts, Ellie has a natural talent for spotting standout fashion and individuality. She joins the judging panel ready to celebrate creativity, personality, and looks that truly make an impression.
Racing TV’s Frankie Foster has become a well-known figure not only for his insightful contributions to horse racing commentary but also for his distinct and stylish presence. A former model with a keen sense of style, Frankie is a fashion-forward personality, whose looks catch the attention of fashion enthusiasts and industry insiders alike.
Mastering your Ladies Day look
As Ladies Day approaches, it's an occasion to showcase your sartorial elegance and sophistication. We will delve into the world of classic race day styles, from refined colour palettes to iconic accessories and impeccable tailoring.
Whether you're a seasoned attendee or a first-timer, join us as we uncover the secrets to mastering classic race day looks that never go out of style.
When it comes to Festival style, there is a lot to think about. But Jade says it’s all down to you: “If you look good, you feel good. It isn’t about chasing trends. It’s timeless. Longevity, practicality, and quality are most important.”
There are endless outfits to choose from, but as a veteran of the Festival, Jade has the answer: “Cheltenham is a showcase, it’s the time to dress to impress. You need to bring a look which is right for the races that can also last you for seasons to come because it is forever in fashion.” she said.
If you really want to nail the Festival fashion, then there are some things you cannot go without. The racecourse is notoriously wet and windy, and many first timers can get caught out by the conditions. For Jade it is all about layers so that you can enjoy your race day to the fullest: “I always say layer up.”
“You will be outside most of the day, so you need something practical, tights under trousers, no one can see them, I always wear my thermals, a thin roll neck under a roll neck makes such a difference.”
Who says practicality forgoes style? Jade accessorises with her favourite pieces. She says “A key accessory that I simply can’t live without at the races would be gloves… It’s always so much colder than you think, so they will not only keep you warm and finish your outfit beautifully.”
Jade adds “Another accessory that really finishes off a look for me is a silk scarf. Our silk scarves are made in England and come in a variety of beautiful colours and prints that are designed to complement all our tweed and tailoring.”
While The Festival is inclusive of everyone’s individual style, there are some things to steer clear of to make the best of your time at Cheltenham. Jade says, “Dress for the weather. It isn’t going to be a day where you can wear a silky dress, it is about outerwear.” Stay away from bare legs, floaty skirts, and thin materials. “The worst thing is when you are so cold, and you can’t get warm.”
Also, sensible shoes. “You’re going to be on your feet for most of the day, moving around the racecourse and trying to see as much as you possibly can. I always wear shoes that I know I can last all day in; it makes such a difference to your experience.”
Jade’s go-to brand is obviously, Holland Cooper. “I love seeing all the different people wearing our collections, it’s great that we cater to so many different styles with our now extensive range of collections”.
If you want to stand out, it’s all about the tweed, our Heritage Collection and our hero signature pieces such as the HC Trench, Regency, Knightsbridge, and Capes are all classics.
Holland Cooper is the obvious choice for this season’s luxury fashion partner, the brand is synonymous with racing style, and will ensure you are fully racing ready, classic timeless style our forever fashion pieces will not disappoint.
