Gentlemen – What to Wear to Cheltenham November Meeting

One of the great autumn jump occasions at Cheltenham Racecourse is the three day November Meeting from Friday 13th November until Sunday 15th November 2026. Friday, day one is the Countryside Day with countryside inspired entertainment. Super Saturday features the Paddy Power Gold Cup, the showpiece of the meeting and Sunday is Carnival Sunday, a fun-filled day for all the family.

Official Dress Code

Officially there is no dress code – their motto is ‘Dress to feel Your Best’ even if that is a nice sweatshirt, pair of jeans and clean trainers.
However for a big race meeting such as The November Meeting most racegoers choose to dress up. Whichever you decide remember to dress for the weather. Fancy dress is permitted as long as the outfit is not offensive and the racecourse reserves the right to decline entry should the need arise. Sports team kits are not permitted.

All prices are correct at time of publishing

Countryside Day

Cheltenham describes this day as “Where the great outdoors meets the home of jump racing” “A day for anyone who loves the countryside and the traditions that make it special.” We Say…Embrace the Countryside Theme of this meeting with at least one piece of tweed or heritage cloth, whether it is a full three piece tweed suit or just a tweed cap. Tweeds add colour, texture and patterns that a normal business suit can’t.

Tweed traditionally comes in muted earthy colours which suit men with warm and muted colouring, but you can also find bright earthy shades such as Joe Browns’ Heritage Houndstooth Blazer in multi colours including bold burgundy, £120.00 with matching Heritage Houndstooth Trousers £69.00. Add another layer with their Opulent Cord Waistcoat in burgundy which will bring out the burgundy in the suit. £55.00 Wear with their Delightful Double Collar Smart Shirt , a white shirt with a purple and pink floral trim £35.00. Choose a brogue shoe East Side Leather Brogues in a bright deep red, £75.00. Traditionally brogues are worn with tweed and they are also good for walking on soggy ground, after all this hardy shoe came from soggy origins. Originating in Scotland and Ireland, it started as a heavy untanned leather with perforations which were not for decoration but to allow water to drain from the shoes whilst walking through bogs and other wetlands. It became a country walking and sports shoe when the gentry saw the benefits. Another way to add personality and brighten your outfit is with a pair of colourful or patterned socks. Dandy Argyle Socks in a pack of 5 will give you a choice of which colour to wear. £25.00. Accessorise with their countryside Fox Pin £5.00 and keep up the red colour palette with their Red Metal Bracelet £25.00. Wrap up the countryside look with their Sullivan Style Flat Cap in brown and crafted from durable wax fabric that is ready to face the elements £25.00. It may be mild enough to just wear your suit or blazer, but taking a scarf is a good idea. Maverick Men’s Striped Scarf £20.00

Super Saturday

Cheltenham says “One of the most anticipated race days outside of the Cheltenham Festival” and “When the racing finishes, the dancing starts” We Say…This may be the day you want to dress up.

Keep warm but stylish with a wool blend suit. Best mates? Go in the Best Mate Enclosure for the best views of the racing directly opposite the main grandstand and adjacent to the finish line. Best Mate is a favourite spot for groups and showing off your dapper style. Ben Sherman has the perfect wool blend suits for different skin tones: For the cool skin tone, go for  Crepe Stripe Jacket K in cool charcoal. Crafted in 70% Wool, 28% Polyester, 2% Elastane, was £195.00 now £90.00 with matching Crepe Stripe Trouser in Charcoal was £110.00, now £50.00. Here matched with their Long Sleeve Paisley Print Shirt in dark navy, £75.00 For a warmer skin tone, choose their Ombre Check Jacket in Dark Wine in 70% Wool, 28% Polyester, 2% Elastane, was £195.00 now £90.00 and matching Ombre Check Trouser in Dark Wine were £110.00, now £50.00.  Pair with their Long Sleeve Paisley Print Shirt in Maroon was £75.00, now £52.00. Although your suit is a wool blend, you still may need to layer up. A cardigan is a good choice, it allows your patterned shirt to be on show whilst it stays hidden underneath your jacket. Long Sleeve Texture Cardigan in Dark Navy 70% Acrylic 30% Wool, £95.00. Whichever suit you choose sparkle in those dancing shoes: Kurt Geiger’s Hugh 2 Loafer in cool grey houndstooth upper with crystal embellishment The vamp is topped with an antiqued silver metal eagle head emblem with crystals. £199.00. Accessorise with pearls by Dower and Hall: For cool tones choose their Tahitian Luna Pearl Pendant a black Tahitian pearl sourced from the pristine waters of French Polynesia on a 22 inch sterling silver chain £225.00. Layer with their  Dove Grey Freshwater Luna Pearl™ Necklace £245.00 For warm tones choose their Oval White Freshwater Pearl Pendant on a 22 inch yellow gold vermeil chain £190.00. Layer with their White Freshwater Luna Pearl™ Necklace £245.00. Top it all with Cotswold Country Hats Pork Pie Hat in navy, £38.95 and wrap it up with Geoff Stocker’s ‘Saxon’ Scarf made from a woven mix of 70% wool and 30% silk and double sided style in bronze and blue colourways £95.00.

Carnival Sunday

Cheltenham say “Carnival Sunday brings the local community together for top-class racing in a relaxed and welcoming atmosphere. The day features six exhilarating races, Shetland pony racing, and a host of family-friendly entertainment, from fairground fun and circus shows to meeting real dinosaurs and discovering our mini zoo. With plenty to see and do, it’s a fun-filled day out for all the family.” We say.. This is the most relaxed casual day, so dress to feel comfortable whilst having fun.

Corduroy is back on trend for 2026. Wrangler’s Loose Straight Corduroy Trousers are crafted from soft touch chunky corduroy in rich coffee brown. 90s inspired with a slouchy loose straight silhouette, £75.00. Pair with their Relaxed Pullover Sweater in bitter chocolate, was £85.00 now £59.50. A blend of 50% cotton,45% nylon and 5% wool, it features a Western-inspired pattern on the front and back, a nod to their American roots. The relaxed loose fit is perfect for layering underneath with a shirt  Regular One Pocket Shirt a large overcheck in shades of brown, made from 100% cotton twill in a heavier weight for the colder months, £55.00 and of course a Regular Small Graphic Tee in 100% cotton almond milk shade, £30.00. Finish off layering with their Regular Wool Trucker Jacket in a bold olive check with a cosy brown sherpa interior and collar, £160.00. You will be outside most of the time so step out in Lanx’s Axis Chelsea Boot which are made from a durable, waxy, water-resistant suede in treacle brown with a rubber sole, combining exceptional grip, water-resistance, and comfort, £250.00. Wear with their Thick Sock in tango orange. This thick sock is a perfect partner to a pair of boots. Made with 90% cotton & 10% nylon with a seamless toe. £19.00. Complete the look with Cotswold Country Hats’ Distressed Leather Bakerboy Newsboy Cap in brown, £49.95. Accessorise with Coeur De Lion’s 3 strand Leather Bracelet combining smooth and braided brown leather in a multi-strand design with cube elements made from brown and golden tiger’s eye and grooved stainless steel, £85.00  

Joe Browns images courtesy of Joe Browns marketing team

Ben Sherman images provided by pr agency We Are Village PR

Dower & Hall and Coeur de Lion images courtesy of pr agency We Are PR UK

Kurt Geiger images courtesy of Kurt Geiger

Geoff Stocker images courtesy of Geoff Stocker

Wrangler images provided by pr agency Fabric PR

Lanx shoes images courtesy of pr agency Harriet Fields Communications

Cotswold Country Hats courtesy of Cotswold Country Hats.


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