Style /

Cheltenham Style Guide: What to Wear

Outfit inspiration coming in thick and fast, Cheltenham-style.

This post may contain affiliate links. Learn more


You might’ve heard the words Cheltenham Festival echoing around the town (and the rest of the country) recently. That’s because, the famous racing event that is an indisputable staple in England’s sporting calendar, is returning again for ‘Four Days or Extraordinary’. Sponsored by Magners, Cheltenham Festival runs from Tuesday 12 – Friday 15 March and is the set to be the most exciting, highly anticipated Jump racing event of the year. It’s set at Cheltenham Racecourse and will play host to 260,000 visitors and the absolute finest horses and jockeys, trainers and owners. What they’re racing for? Awards, reputation – and over £4.5m worth of prize money. But Cheltenham isn’t all about the sports – it’s a stylish parade of the finest brands and outfits worn by Britain’s best. There isn’t an official dress code, and the organisers recommend dressing for the weather; so if you’re going, and aren’t sure how to create a look that is appropriate for the festivities, the weather and for yourself, let our Cheltenham style guide help you. 

Cheltenham Style Guide: What to Wear

Outfit 1

Cheltenham outfit 1

Miu Miu Floral organza mohair and wool-blend blazer, £2,265, | Button-embellished crepe trouser, £550, | Antonia Bag in Cream, £450, | China Red Lamb Glove, £290, | Red Bloomsbury Silk Neck Scarf, £80, | Leider Boots, £680, | Cashmere Turtleneck Sweater, £450,

Outfit 2

Cheltenham what to wear - outfit 2

Mariano Dress, $2,500, | Gianvito Rossi Laura 85 Leather Knee Boots, £1,110, | Gate Small Bag Amber/Light Grey/Rust Colour, £1,350, | Camel Double Breasted Tailored Coat, £790, | Saint Laurent Shearling Jacket, £4,200,

Outfit 3

Cheltenham what to wear outfit 3

Racil Max striped linen shorts, £315, | Interlocking G Tights, £85, | Brock Collection Orth peplum hammered-twill jacket, £905, | Satin Platform Sandals in Fuscia, £700, | SS19 La Riviera Le Baci Fringed Raffia Bag, $588, | Sophie Buhai Silver, Shell and Onyx choker, £765, | Slip Silk ribbon and hair tie set, £45,

Outfit 4

Cheltenham what to wear - Outfit 4

Polo Ralph Lauren Straight Leg Trousers, £145, | Haider Ackermann Jagger double-breasted cotton-twill blazer, £1,070, | André shirt, €180, | Calvin Klein Chris leather Chelsea boots, £778,

Outfit 5

Cheltenham what to wear - Outfit 5

Chino Parfait, €190, | Wooyoungmi Striped jersey rugby shirt, £310, | A-Cold-Wall* Logo-intarsia ribbed-cotton socks, £45, | Soft Booties, £840, | YOU MAWO Malina Sunglasses, £600,

The C&TH Magazine Cover Archive | The Best Yoga Studios in London | Find Daily Shopping Inspiration on the Luxury List