Race Day Dressing: Laylaleigh at Cheltenham Festival 2026
Cheltenham is always one of the most special moments in our calendar, and this year was no exception. There is something quite magical about seeing months of design, careful craftsmanship, and conversations come to life trackside, worn with confidence, personality and joy.
Each piece we create is never just a hat. It is a collaboration, a reflection of the woman wearing it, and a finishing touch that brings an entire look together. Cheltenham gives us the most wonderful opportunity to see that in motion.
We were so proud to see so many of our lovely clients wearing Laylaleigh across the week.
Tigger looked incredible across the festival, wearing two very different pieces, each perfectly suited to the day. For one look, she chose “Jessica” in blue, a beautifully balanced felt design with soft detailing that felt both classic and fresh. For Gold Cup Day, we created a bespoke piece for her using felt, feather and veiling, bringing together texture and movement for something a little more dramatic.
Aly looked absolutely stunning in “Raya”, a design crafted from felt, veiling and silk flowers. We chose a deep navy tone to complement her tailored tweed suit from Holland Cooper accented with jewellery from Boodles, allowing the textures to do the talking while keeping the overall look refined and elegant. Seeing it worn in the heart of the action was such a proud moment.
Laura wore our “Olivia” design beautifully, styled effortlessly across the day at Cheltenham. Crafted from felt and finished with a flurry of feathers, Olivia is one of those pieces that feels both timeless and expressive. It brought such lift and personality to her look, and is a perfect example of how the right headpiece can completely transform an outfit.
To every client who chose Laylaleigh this Cheltenham, thank you. It means the world to see you wearing our designs, feeling confident, and enjoying your day.
And to those who stopped us, messaged us, or are already planning for your next event, we cannot wait to create with you.
If you are thinking about a piece for your next race meeting, wedding or special occasion, do get in touch. Whether bespoke or from our collections, we would love to help you find something that feels entirely your own.
Here’s to the next big meeting.
Leigh x