Cheltenham Races Dress Code

An invite to Cheltenham with my daughter? We had to rise to the occasion—and the outfits! Cheltenham in November has its own unwritten dress code: practical country polish with a big dose of elegance. Think British style that can handle a chilly breeze and a bit of grass underfoot.

Summer race days are all about floaty dresses and fancy hats, but Cheltenham at this time of year is about smart layering. Skirts are timeless, but trousers are widely seen. A wool coat or tweed jacket is de rigueur, and a felt or wool hat instantly looks the part. Block-heel boots are your friend—country-chic and you won’t sink into the turf.

What to wear at Cheltenham Races

Sophie’s a seasoned Cheltenham-goer and nailed it: head-to-toe black topped with a camel hat for structure and warmth, plus block-heel boots. Effortless and spot on.

I went with a beautiful jersey blouse (new purchase!) and, would you believe, I’d found the perfect hat last month! Paired with tailored navy trousers and long black boots, it felt just right for our hospitality venue. I was missing a coat, but luck was on my side. A quick nip into a dress agency in town and there it was: the perfect long navy coat - wool and cashmere, nipped at the waist, elegant but warm. It was meant to be.

I finished the look with a cherry-red scarf at the neck and a silver brooch for a little sparkle. And yes, I ignored the fact that navy never perfectly matches navy—that’s half the charm.

Blouse (exact) | Bag | Tailored trousers | Boots | Hat | Coat (items are similar)

Eating and drinking at Cheltenham Races

Food and drink at Cheltenham cover all bases, from sandwiches and street food to full-on fine dining. We were in the Horseshoe Pavilion with a fabulous lunch menu and a big screen, which turned out to be ideal as the weather didn’t exactly play ball. Honestly, it was brilliant inside: a light-hearted buzz, everyone chatting, swapping tips, a few cheers rolling across the room as the races got going.

We put a bet on every race, had one really good winner, a couple of seconds, and came out roughly even - always the best feeling. The whole day had that mix of glamour, good fun, and a little flutter of excitement. If you’re going, think warm, polished layers, a hat you love, boots you can stand in, and go ready to soak up the atmosphere.