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 14th November until Sunday 16th November 2025. Friday, day one is the Countryside Day with countryside inspired entertainment. Saturday is the Paddy Power Gold Cup, the showpiece of the meeting and Sunday is the Family Fun day.

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

Embrace the Countryside Theme of this meeting with at least one piece of tweed, 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.

Tips on How to Wear Tweed.

Smaller guys (short or in weight) should avoid the larger checks as these will just drown their frame. Go for the smaller checks. The more textured tweeds are heavier so will add bulk – good for the skinnier guy. The heavier or more rounded guys should go for the less textured tweeds and the less structured soft tweed jackets. Tweed traditionally comes in muted earthy and autumnal colours which suit men with warm and muted colouring. Keep the warm muted colouring with shirts and jumpers to complement the look such as a cream shirt or an orange jumper. But don’t worry if your colouring is not warm and muted, there are some tweeds out there in bolder brights and cooler colours such as blues. Or if you already have a tweed jacket in a warm colour, just team it with cooler shades of pinks and blues to add more contrast and brightness. 

For a quirky sartorial look, mix and match your colours and patterns such as wearing Joe Browns Charming Herringbone Blazer £110.00 with their Bias Check Waistcoat £59.00 or wear with a knitted waistcoat in a bold colour such as their Stylish Green Knitted Waistcoat £45.00. Both these will add an extra layer of warmth. For a smart casual look team with their Terrific Tapered Jeans £45.00 And really mix up your tweed with their Mixed Tweed Hat | Accessories | Joe Browns £45.00
The Brogue ShoeWest Coast Leather Brogue Boots £90.00
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.

The Scarf – It may be mild enough to just wear your suit/jacket but taking a scarf is a good idea. A scarf will not only give some warmth it it turns a bit cooler but will also add a pop of colour to your outfit. If If you are wearing tweed, then bring out one of the colours in the pattern. It doesn’t have to be the same shade and it doesn’t have to be the dominant colour in the pattern.

Images provided by PR Shots


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