Cheltenham Festival Fashion

What to wear to the Cheltenham Festival

Wondering what to wear to the Cheltenham Festival? This complete guide to Cheltenham Festival fashion will have you dressed to impress, but more importantly dressed for the weather. It can we bitterly cold at Cheltenham in March and conditions underfoot can be softer and muddier than you first anticipate. This handy little guide will keep you informed with the latest fashion advice and inspire your track-side attire.

The gentleman’s guide to Cheltenham Festival fashion

TWEED CAP

Old boy wearing a cap he’s owned for 40 years, young lad earning his stripes in the ways of the horsey set or hipster from the city unsure whether he’s wearing it ironically. Doesn’t matter who it is, though – the tweed cap works, so just join the party.

BARBOUR WAXED JACKET

Absolutely de rigueur at Twickers, of course, but the Barbour jacket is plenty country enough too. An excellent alternative to tweed, if you don’t want to overdo said look – although why you wouldn’t want to is frankly beyond us.

BINOCULARS

A must for racegoers keen to see the horses fly down the remote back straight. The proliferation of huge screens around the course means you’ll never actually use them, but that shouldn’t stop you wearing them round your neck all day anyway.

COLOURFUL STRIDES

Straight from Putney, a well-tailored pair in a colour you would never normally wear. Mustard is a decent shout; otherwise, bright red, even brighter blue or purple will suffice.

GUINNESS

Doesn’t matter if you like Guinness or not – it’s everywhere. Throwing down an early pint doesn’t just settle the stomach for ahead of a busy day; it also establishes you as a man who is meant to be there.

BROGUES

The horsey set can get away with wearing whatever they want on their feet, largely because they were up at 5 am and you weren’t. If you want to smarten up though, brogues are the pick. With a nice shine, if you have the energy to work one up.

The lady’s guide to Cheltenham Festival fashion

FEDORA

Also an option for the gentlemen, but the reality is this: every single woman on this planet looks better than every single man in an equivalent hat, and you know it. That means you get first choice, ladies – and that means you get to choose the fedora.  

CASHMERE SWEATER

Under regulation tweed is where you have a real chance to dazzle. So get involved with pink cashmere. Any bright colour will work, but going for pink or red enables you to accessorise with matching lipstick. Seriously.

TWEED SUIT

The polo groupie look – white jeans, navy blazer – is popular, but this is about going all out. Enter the full-on tweed two-piece suit, with skirt to match jacket. There is nowhere else on earth you will wear it, which means you can recycle it every ruddy year.

RACING POST

Strolling around with a copy under your arm is a definite yes. Very important point: if the horse you back actually wins, you are expected to holler loudly while chicking your Post high in the air. Those well-practised in the art catch it on the way down.

CHAMPAGNE

The Cheltenham female isn’t afraid of mucking in with the lads on the hard stuff, but every day’s racing should start with at least one glass of fizz. Make that two, actually. It is the festival, after all.

RIDING BOOTS

Almost sacrilege to suggest anything else, really. But if you’re going to enjoy Cheltenham fully, you should get about a bit: Guinness Village, parade ring, trackside. Riding boots make this a lot more straightforward than any kind of heel, particularly if the aforementioned fizz has gone down well.