Fashion Shines Bright on Ladies' Day at Cheltenham Festival 2026

Ladies' Day returns to the Cheltenham Festival 2026, showcasing stunning fashion and headgear alongside thrilling races, with cash prizes for best outfits and notable VIP guests attending.

Return of Ladies' Day at Cheltenham Festival

Ladies' Day has made a notable return to the Cheltenham Festival this year, drawing as much attention for its fashion as for the horse racing events. The festival commenced on Tuesday and continues to attract hundreds of thousands of attendees to the Prestbury course in Gloucestershire.

A young woman with wavy blonde hair smiles as she poses for the camera at Ladies Day at the Cheltenham Festival 2026. She is wearing a plum red berry-style beret with feathers attached to it, and a jacket that matches her hat

The event is set to conclude on Friday with the sold-out Gold Cup day, which will welcome 70,000 racing enthusiasts.

Revival of Tradition and Style Competition

After being rebranded as "Style Wednesday" last year, Ladies' Day has reclaimed its traditional name in 2026. This change comes alongside the introduction of cash prizes awarded to those sporting the best outfits, adding a competitive edge to the fashion on display.

A line of women laugh as they pose for the camera at the start of Ladies' Day at the 2026 Cheltenham Festival. Some of them have bright yellow or blue outfits on, and all of them are wearing bright fascinators on their heads

Distinctive Fashion and Headgear

As always, Ladies' Day is synonymous with eye-catching outfits and elaborate headwear. This year has been no exception, with many attendees arriving early on Wednesday to showcase their elegant and creative attire.

A woman with large sunglasses and a white, fluffy hat poses for the camera as Ladies' Day gets under way at the Cheltenham Festival. Behind her is a mixture of blue sky and cloud

Four women, three of them young and one slightly older, smile as they stand arm in arm at the Cheltenham Festival. They are all wearing smart dark jackets and hats or fascinators

A woman with a black and white checked jacket holds onto a dramatic piece of headgear at the second day of the 2026 Cheltenham Festival. The hat is made of long, curling pieces of black and purple material

Men's Bold Fashion Statements

While the focus on Tuesday is traditionally on the ladies, several male racegoers also embraced the opportunity to make bold fashion statements. Their distinctive suits and colorful ensembles contributed to the vibrant atmosphere of the day.

Two men face each other as they chat while holding drinks. One has a shiny orange formal suit on, while the other is wearing a light blue suit with colourful emblems on it

Notable Guests and Early Festival Scenes

Among the VIP guests present on Tuesday was darts player Luke Littler, who added to the event's high-profile attendance.

Darts star Luke Littler walks into the Cheltenham Festival, with his other guests either side. He is wearing a dark blue suit and waistcoat, a white shirt and dark pink tie and sunglasses — Darts player Luke Littler was among the VIP guests on Tuesday

Early morning scenes on the second day featured striking silhouettes of horses and riders against a bright sky, capturing the essence of the Cheltenham Festival.

A horse and rider are silhouetted against a bright sky early in the morning on day two of the Cheltenham Festival 2026

Group Fashion Highlights

Groups of attendees, including young women dressed in tweed and smart jackets paired with hats and fascinators, posed confidently for photographs, highlighting the social and stylish aspects of the festival.

Five young women pose with their hands on their hips side on to the camera. They are all wearing tweed or smart jackets and dresses with hats and fascinators.

Women of various ages also gathered, all adorned with fascinators featuring feather details, complementing their smart coats, jumpers, skirts, and dresses.