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Best Dressed competition

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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.

Entries can be submitted on course via the Best Dressed QR code - entries must be submitted by 14:30, with category winners presented following the feature race at 16:00.

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Prize Sponsors 2026

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.

 

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.

 

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Mastering your look

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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.

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FESTIVAL FASHION TIPS WITH JADE HOLLAND COOPER

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.

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