What to Wear to Cheltenham Races: A Winter Style Guide 2026

Mud on your boots, frost on the hill and the thunder of hooves as the field comes round the final bend. Winter racing at Cheltenham is one of our favourite days out of the year, and it's the one we design for.

The November Meeting (Friday 13 to Sunday 15 November 2026) is the first big weekend of winter at Prestbury Park, with Countryside Day, Super Saturday and Carnival Sunday. It's also a chance to try out your race day wardrobe before the Festival in March.

This season we've added new wool jackets and coats to the collection, and they're made for exactly this kind of day. Here's how we'd wear them.

Start with a new season jacket

A good jacket does most of the work on race day. It keeps you warm in the stands and still looks sharp when you take your coat off in the bar. These are new to the collection this season.

• Grantham Check Wool Jacket in Sage or Midnight. You might have spotted it in The Gentlemen. The check feels at home in the country, but the cut is clean and modern.
• Knightsbridge Cashmere & Wool Jacket in Chocolate Brown or Wheat. Cashmere makes it soft enough to wear all day, and brown is the colour of the season.
• Ascot Navy Pink Wool Jacket. Navy wool with a hint of pink, and a name that belongs at the races.
• Knightsbridge Duck Egg Wool Jacket. A pale blue that looks lovely against grey skies and green turf.
• Belgravia Moss Green Jacket. Deep green, perfect with tan leather and brown boots.

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Knits for a frosty start

The first race is usually the coldest. Wear a soft knit under your jacket so you're warm from the moment you arrive, then take a layer off if the sun comes out.

• Turtleneck Dot Jumper in Navy, Chocolate or Oat. A high neck keeps out the cold, and the dots add a little fun.
• Verity Button Cardigan. Easy to slip off in the bar, easy to put back on for the last race.
• Cable Knit Jumper in Camel, Oat, Navy and more. A proper winter jumper that sits well under a wool jacket.
• Mocha Faux Fur Gilet. Wear it over a knit for extra warmth on the coldest days.

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When the weather turns

It's Gloucestershire in November, so plan for rain, wind and everything in between. A long coat over your jacket means the weather never spoils the outfit.

For a dry, cold day

• Oxford Wool Coat in Navy or Amber. Clean tailoring that goes over a jacket without looking bulky.
• Demelza Camel Wool Coat. Classic camel that works with every colour in this guide.

For a wet day

• Eleanor Navy Quilted Waterproof Coat. Quilted for warmth and fully waterproof, so you can stay out on the rail when others run for cover.
• Louise Poppy Lined Wax Coat in Mahogany or Racing Green. Waxed cotton in true country colours, with our poppy print inside. You may have spotted our Louise Deluxe Check Wax Coat in MobLand, worn by Dame Helen Mirren. 

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Underfoot

Cheltenham is a big course, and you'll cover more ground than you think between the parade ring, the stands and the bars. Pick shoes you could happily walk in all afternoon.

• Sloane Waterproof Boots in Navy or Mocha. Our answer to a soggy day: smart enough for the Club enclosure, tough enough for the mud.
• Ranger Brown (Extra Fit) Waterproof Boots. A roomier fit with space for thick socks on a freezing day.
• Beth Suede Boots in Tan or Navy. A neat suede ankle boot for a dry day, lovely with jeans or a midi skirt.
• Hackney Suede Loafers in Navy or Burgundy. For a day in hospitality, where you'll be indoors more than out.

Skinny heels and soft turf don't mix, so if you want height, go for a chunky block heel.

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The details

The finishing touches are what people remember, and in winter they keep you warm too.

• Jesse Suede Hat in Tan or Navy. A winter alternative to a fascinator, and it keeps your ears warm.
• Wax Deluxe Check Cap. A wax cap that shrugs off a shower.
• Alaskan Scarf in Stag, Pheasant Green, Pheasant Navy or Dog. Big, soft and covered in country prints, so pick the one that suits you.
• Leather & Suede Driving Gloves in Chocolate or Camel. Warm hands for clapping home a winner.
• Lion Belt in Tan or Navy. Cinch it over a knit or coat for shape.
• Phillipa Leather Handbag in Tan or Navy. Everything you need for the day, nothing you don't.

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Three days, three outfits

Friday: Countryside Day
The day that celebrates rural life, so go full country. Grantham Sage Check Wool Jacket, Cable Knit Camel Jumper, Sloane Mocha boots and the Alaskan Pheasant Green Scarf.

Saturday: Super Saturday
The biggest crowd of the weekend, so make it your smartest look. Knightsbridge Chocolate Brown Cashmere & Wool Jacket over the Selsey Navy Blouse, Beth Tan Suede Boots, Lion Tan Belt, Phillipa Tan Leather Handbag and the Jesse Tan Suede Hat.

Sunday: Carnival Sunday
Relaxed and family friendly. Demelza Camel Wool Coat, Turtleneck Dot Oat Jumper, your favourite jeans and Hackney Burgundy Suede Loafers, with Camel Driving Gloves tucked in your pocket.

Cheltenham style questions, answered

Does Cheltenham have a dress code?

Not a strict one. The racecourse asks racegoers to avoid wearing sports team kits, but otherwise you're free to wear what you like. Most people dress up, especially in the Club enclosure and hospitality.

How do I dress for Cheltenham in November?

Layers. A knit under a wool jacket, a long coat on top, waterproof boots if it's wet, and a scarf and gloves for the afternoon.

Are jeans OK at Cheltenham?

Absolutely. Pair dark jeans with a tailored jacket and suede boots and you'll look right at home.

Should I wear a hat?

You don't have to, but it finishes a race day outfit beautifully. In winter, a suede hat or wax cap is more practical than a fascinator.

What boots are best for Cheltenham?

Waterproof boots with a low heel if rain is forecast, or suede ankle boots on a dry day.

Your next race day

We'll be updating this guide ahead of the Cheltenham Festival in March, so save it for later. Until then, explore our new season jackets, coats and accessories.

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