Dressing For Cheltenham Festival: A Style Guide For A Day At The Races

The Cheltenham Festival marks the beginning of the racing season in the UK, leading the way for The Epsom Derby, The Grand National, and of course, Royal Ascot, where patrons really dress to kill. In a way, Cheltenham makes a nice lead in for the nation’s social season – it has no strict formal dress code, leaving punters free to ease themselves into the swing of things. 

That said, there are few better excuses to dress up than for Race Day, and even at Cheltenham, there are always scores of people pulling out all the stops when it comes to how they dress for this thrilling and prestigious event. 

Below we have provided a style guide to steer you in the right direction, ensuring that you feel and look your best.

A brief look into the story of the Cheltenham festival

The earliest recorded races in the Cheltenham area date back to around 1815 with the Cheltenham festival beginning in 1860, providing a long-standing history and an ingrained culture that not only focuses on horse racing, but fashion too. The festival spans over four days presenting a range of thrilling events, elegant attire, and delectable food and drink. 

There are four big races – the anticipated main event, the Cheltenham Gold Cup, attracts visitors from all over the country and its surroundings to attend this iconic festival at which one can indulge in the high life and dress to impress.

Essential pointers to consider when choosing a style for Cheltenham

Dressing for the weather is a vital matter to note at Cheltenham. Previously it has proven to be rather chilly, but in spite of that don’t let those odds get in the way of the flawless looks you’re able to put together. If anything, dressing for slightly colder weather allows for even more possibilities.  

There are a few key elements to keep in mind that will encourage an all-around enjoyable experience. Colours and styles vary from season to season, and from environment to environment, but for the racetrack, it’s hard to go wrong with earthy tones like olive, soft grey, deep browns, and midnight black. These can be worn effortlessly together, or stand alone for a statement. These colours can be incorporated into several, established and timeless suit styles. 

Let’s explore some of the options:

Country & Tweeds

Dating back to about 1831, this fabric was associated with the elite and has become an archetypal statement throughout men’s fashion. Tweed suits are one of the more[popular outfits at the Cheltenham festival, and with good reason too. As time has progressed we have seen modifications and variants of this particular style, noting ranges from the more hardy types such as Harris Tweed, to the softer versions such as Silk Tweed. It may be considered old fashioned for some, however, if accessorised correctly, a pop of colour in the form of a pocket square and or tie, will emanate an air of the distinguished and classy. Check out our Country & Tweeds Style Guide for a closer look!

The Classic Suit

It’s safe to say that this can be worn to almost any formal occasion. One cannot go wrong with the classic style of a suit. If you’re looking to stay within a safe bracket of expenditure and dressing up isn’t your thing, we can provide you with some direction. Take note, it’s important to decide on a fabric that stands out. Colour choice is key! Whether it’s your tie, or pocket square, make sure to blend your colours accordingly. Nobody wants an unwanted clash. Have a look at our Business Suits Style Guide for more details on things you should consider when getting a tailored suit. 

The Three Piece

As we have noted, the weather is a large, depending factor at Cheltenham. If you’d like to keep the accessories to a minimum, adding a third layer of fabric in the form of a waistcoat will do the trick. This will ensure that you stay warm, and keep you streamlined at the same time. 

The Three-Piece Suit is simple, but keep in mind that your waistcoat should fit your body correctly. If double-breasted, all the buttons should be done up, if we’re dealing with a single button line, we recommend leaving the bottom button undone for that added flair. . 

Generally, the fabric and colour for all three pieces should be the same, but if you’re feeling a little experimental,  you can venture into the world of a two-tone. Do make sure to do your research to pull off this combination correctly.

The Jacket or The Topcoat

Given the less formal atmosphere (and the unpredictable weather) at Cheltenham, donning a smart casual jacket or a topcoat is a great way of staying stylish while steering clear of the classic suit. 

You can still pair a tailored blazer, sports coat or smart casual jacket with a pair of chinos or trousers of a different colour, and look fantastic in and around the track.The right topcoat can be worn over a suit of course, but also looks fabulous with chinos, trousers or jeans. Choosing suit separates however, requires an understanding of a few fundamental dressing principles, which we’ve written about in our Bespoke Jackets & Separates Style Guide

For inspiration on what kind of overcoat or topcoat to consider, read our Overcoats & Topcoats Style Guide.


Aim to keep it simple with accessories, the trick is to not over do it. Being subtle often speaks volumes. A pocket square and a tie can be just enough to finish off an outfit. When it comes to shoes, Brogues are a common accompaniment, however, the ever-trendy leather Chelsea boot is a reasonable choice for practicality and comfort.

So there we have it, the possibilities are boundless when choosing a look for this esteemed affair.  Whether you’re a man that prefers a more extravagant outfit, or something toned down, there is a plethora of ideas to pick from and the promise of gliding your way through this event in luxurious fabrics can almost ensure that it will be memorable.

We trust this style guide helps. Make an appointment with Marc Oliver Bespoke Tailors to arrange a fitting for your next overcoat or topcoat. Sit down with our expert tailor, discuss your needs and wishes, and enjoy the Savile Row tailoring experience. 

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