What to wear to Cheltenham Festival – with Alice Hare

As with all good race meetings, there’s a universally acknowledged but simultaneously unspoken dress code at the Festival. Get it wrong and immediately not only mark yourself out as an outsider but risk a miserable day due to impracticality. Not exactly a recipe for happiness. Heed my warning: Cheltenham is cold. Very. It could be a pleasant day on the outside world but enter the racecourse’s gates and an icy wind akin only to that of the White Witch’s Narnia descends. I jest not. It’s a truth universally acknowledged amongst racing fans, a mystery inexplicable but accepted. Il fait très froid. Hace muy frío. Got it? 

Faced with such elements, there’s only one sartorial solution. Enter tweed. Warm and waterproof, it’s become a true uniform of the Festival. While at other jumps season meetings, other winter fabrics abound in addition to tweed, Cheltenham is very heavily tweed-leaning. It’s useful to have such a specific dress code (especially when it’s an unspoken one), but this perceived simplicity is deceptive, for with it comes the risk of looking like every single other person there. How to demonstrate individual style while still looking like you emerged from the womb tweed-clad and Cheltenham-ready? Read on for my guide.

Women’s outfits for Cheltenham Festival

Use a three-piece tweed formula as the base of your outfit and add individuality from there through clever accessorising. Schöffel’s Beauly Skirt, Millport Waistcoat and Portree Coat are a style triple threat. Their British-milled tweed delivers lightweight warmth with zero stuffiness, while their jewel-hued satin linings are all kinds of luxe. Layer underneath the Fakenham Shirt. Its piecrust collar is all kinds of ‘80s Princess Di – I like to accentuate it and make sure it stays sitting super high by tying a velvet ribbon around its neck. (My four sisters tell me I look like either a choir boy or a ruff-wearing Tudor when I do this. I like to remind them of my chosen profession at this point). Choose a velvet ribbon in the same shade as the rest of your accessories and purchase a spool of it from Amazon for under £5. It also adds an androgynous, bowtie-esque touch to an otherwise-girly look. 

Ribbed tights will protect your legs from Cheltenham’s notorious chill – I adore a sheer tight but they’ll only work at Cheltenham if you want shivers that make your knees knock. The bordeaux and brown pairs worn by our model here I bought from ASOS. Shoe-wise, eschew the knee-high boot you might naturally reach for to go with this look (everyone else will be wearing them) in favour of an on-trend Mary Jane – they unite form with function (hello, comfortable block heel). Our model is wearing a Penelope Chilvers pair in cinnamon velvet, complete with gold buckle and gold heel. Give velvet or suede styles a spray with Crep Protect before heading to the Festival – it’s a suede waterproofer I swear by for protecting shoes from mud and rain. 

A bag with a top handle you can sling onto your wrist means you’ll be able to juggle Guinness, race card and greeting people without helplessly grasping at a clutch bag too. I’d use headgear as a means of counteracting the practicality of the tweed with some opulence – think regal, diadem-style headbands and elegant, vintage-inspired beret and cloche styles. Put simply, go extra. Our model’s burgundy velvet headband is by Emi Milverton, and her camel beret-style hat is by Lock & Co – the oldest hatters in the world, no less. I’m also slightly obsessed by the faux fur hat Pippa Middleton wore to Cheltenham in 2013 – an instant injection of undiluted, unapologetic glamour to practical tweed. Head to Helen Moore for similar options.

Men’s outfits for Cheltenham Festival

Again, opt for a tweed base and build from there. More specifically, it’s Schöffel’s St. Andrews Tweed Sports Jacket and Ross Tweed Trousers you’re after. Underneath, a checked shirt, particularly a Tattersall, is perfectly at home at Cheltenham. Its check is named after the horse market of the same name, after all. Luckily, Schöffel is to men’s checked shirts what Hamleys is to toys. Their Burnham Tattersall Shirt will do nicely.

Next? The tie. A race day essential, in my opinion. (When I am queen, my first law will be to make the wearing of suits without ties illegal). And even if you opt to wear a more modern, Nehru-collared tweed gilet like Schöffel’s Berwick Gilet to Cheltenham instead of a traditional tweed jacket, a tie is the perfect way to counterbalance that modernity with some old-school tradition. The new burnt orange colourway of Schöffel’s Ashford Silk Tie reminds me of Hermès’s signature orange hue – in short, damn chic. 

For a similarly expert balancing act of modernity and traditional style, I love a tie poking out from under a quarter zip instead of an old-school v-neck or roundneck jumper. Schöffel’s Calton Quarter Zip is just the ticket – its supersoft cashmere/wool mix is sure to combat the notorious Cheltenham chill. A good tweed trouser and covert coat will see you through Cheltenham Festivals for decades to come – it’s the addition of small details like a quarter zip instead of a roundneck, and a Nehru gilet instead of a classic sports jacket, that will modernise your look. 

The last important point for nailing men’s style at Cheltenham: don’t be tempted to scrimp on your hat – it will ruin your whole look instantly. In a market awash with cheap fedoras and trilbies, head to Lock or, for beautiful hats that don’t cost the earth, new kid on the block Tiffers has you covered. 

All that remains? To scramble for a seat on the Paddington to Cheltenham service. Elbows at the ready…