A Guide to Men’s Cheltenham Dress Code with Alice Hare

Alice Hare is a London based stylist and fashion editor with a love of British style and all things country. We asked for her advice on what to wear to the Festival to look at feel your best.
In the words of Deniece Williams, let’s hear it for the boy. The boy at Cheltenham Festival, specifically. (Probably not the same boy Ms Williams was talking about, but I digress). For a background history of the Festival and its very specific but unspoken sartorial code, have a look at my ladies’ Cheltenham fashion guide here. You won’t be surprised to hear that the Cheltenham cold doesn’t discriminate based on gender, and, as a result, warm tweeds are order of the day for the man attending Cheltenham as well as the lady. Allow me to expand.
Unlike for the ladies, where a multitude of equally stylish outfits present themselves as options for Cheltenham in often brain-boggling style, follow a simple formula and it’s hard to go wrong at Cheltenham if you’re a man. Tweed suit, tie, covert coat, felt trilby. For some inspiration before you begin, look no further than arguably the best-dressed man on the planet – King Charles. Look at pictures of him at Cheltenham in the ‘80s and compare to those of him there in more recent years, and you’ll notice it’s always the same formula. Proof that the right tweed suit and covert coat are a lifelong investment that won’t date.
A great suit requires a great base, and for Cheltenham, that comes in the form of a Tattersall shirt. As a fabric steeped in racing history, there’s no better place than Cheltenham for Tattersall. The pattern’s name comes from Tattersalls horse market, founded in Suffolk in 1766 – horses to be sold were paraded in blankets in the check. In the centuries proceeding, it’s become the shirting fabric de rigeur of the countryside and a sartorial unifier as likely to been seen on a duke as it is his gamekeeper. Cordings Tattersall shirt is a true Tattersall in a market swamped by pretenders. Unlike wannabe-Tattersalls, it’s a traditional generous cut – none of the ‘slim fit’ hogwash you see on imitations. Traditionally, this was to allow for ease of movement when shooting. In this case, it allows for gesticulating wildly as the horse you’ve backed advances to the finishing line – naturally.
The next layer? Enter the tweed. Consider Cordings’ house tweed waistcoat, trousers and jacket the Holy Trinity in tweed suiting. Worn together at events like Cheltenham, they’re a country style triple threat, but worn as separates, they’re equally at home at a weekend pub lunch. Try the jacket with stonewash jeans and loafers, and the trousers with a lambswool jumper. And speaking of the trousers, their tunnel top side adjusters = a thousand of the smiley face with heart eyes emoji. The visual equivalent of music to my ears. They allow you to wear the trousers super high on the waist, which is how men’s trousers should be worn – it’s ten times more flattering regardless of body type. Don’t be fooled into the common trap that low-slung trousers will hide a dad bod – they do the opposite.
The pièce de resistance of your Cheltenham look? The covert coat. A total Cordings classic (they made the very first), its cloth is woven by the same Somerset weavers, Fox Brothers, who wove the original cloth over a century ago. Cordings’ make the world’s best – one of London’s finest tailors, Mark Powell, buys his covert coats from Cordings rather than making them himself. Available in beige and navy, it’s a wardrobe staple for both country and city mouse. The tightly railroad-stitched twill fabric makes it highly durable to country brambles and the District Line alike, and its poachers’ pocket is as perfect for a newspaper and half pint of milk in London as it was historically for game. There’s no item that epitomises country elegance quite so pithily – no surprise that the V&A has a Cordings covert coat in its permanent fashion collection.
THE CHELTENHAM OUTFIT
THE ACCESSORIES
Now come the final flourishes. Final but by no means an afterthought, I might add. For an otherwise perfect Cheltenham look can be quickly ruined by the wrong tie and a cheap-looking hat. I like to adopt a literal, thematic approach when it comes to ties – in this instance, ties adorned with horses and equestrian motifs. When I styled Ascot’s jumps season lookbook recently, I had to sit on my hands to not use Cordings’ champion horse tie by the end of the shoot, as I had used it so much (including as a pocket square in one of the ladies’ looks). Hat-wise, there’s nothing that burns my eyes more than a floppy, flimsy-looking felt trilby. Cordings’s felt trilby is the antithesis, thank goodness. Made exclusively for Cordings in England, it’s the details that make it – hello, the perfect grosgrain ribbon band and a gold satin lining featuring hand-drawn illustrations. And to avoid missing any racing due to blue fingertips? (Always advisable). Leather gloves lined with a luxurious cashmere and wool are your best bet. Men so often forget gloves, but you’ll be thankful when you’re able to see Constitution Hill charge to victory rather than hiding in the loo warming your hands under the hand dryer.
See? Guinness and Cheltenham. Cordings and Cheltenham. Matches made in heaven.