The country set's insider tips on what to wear to Cheltenham Festival

The country set's insider tips on what to wear to Cheltenham Festival

Cheltenham Festival kicks off next Tuesday and while plenty will be marking their race cards and consulting a multitude of sources for tips, the small issue of what to wear will also be front of mind for many racegoers. Cheltenham has a unique look among the race meetings, partly thanks to it being held in March when weather is unpredictable but also because of the smart country set which it attracts. 

Read on for the most stylish attendees' insider advice on how to put your Cheltenham look together...

Practicality comes first and foremost

"It is pretty relaxed to be honest," confides Lady Alice Manners, model, The Telegraph's Country Style columnist and regular Cheltenham attendee. "You really need to remember practicality so I always wear a polo neck because for me warmth is paramount- and you also really need a good umbrella! Ultimately, you're there to have fun and that is impossible to do when you're freezing. You'll still be able to look great."

Lady Alice Manners and her sister Lady Violet Manner at last year's Cheltenham Festival Gold Cup Day
Lady Alice Manners and her sister Lady Violet Manners at last year's Cheltenham Festival Gold Cup Day CREDIT: REX

Although racegoers will all make an effort, Manners observes that looking like you've tried too hard is not the done thing at Cheltenham: "The importance of fashion at Cheltenham is showcased in the underlying effort to be chic in the most simplistic way."

“Think smart country clothing, lots of brown and green combined with plenty of fur and tweed. Most racegoers are practically dressed whilst also ensuring they are stylish and warm” add Alice Thorogood and Rosie Turner, co-founders and designers of country clothing company Hicks & Brown.

Lady Carole Bamford and her daughter Alice at Cheltenham 
Lady Carole Bamford and her daughter Alice at Cheltenham  CREDIT:REX

A great pair of boots will see you through the day

Forget attempting to navigate Cheltenham in elegant stilettos- "you need a good pair of boots with a heel," advises Manners, "avoid a court heel - they would be simply too cold and uncomfortable."


Thorogood and Turner echo that sentiment: "Most of the day is spent on our feet so we ensure our boots are super comfy with a good tread to avoid slipping if it rains."

The insiders' boot tip is Fairfax & Favor's knee-high style. "We see so many racegoers choose our Heeled Regina Boots as the go-to for their festival footwear,"  say Marcus Fairfax Fountaine and Felix Favor Parker, co-founders and designers of Fairfax & Favor. "The boot is crafted with an elastic panel that can stretch up to 3cm and sports a flattering 5cm heel to give you elegance without sacrificing comfort," they explain. "The boot is handcrafted with the finest soft suedes which features a feminine, tailored design.” 

fairfax and favor boots

Regina boots, Fairfax and Favor, £345

On Ladies' Day, you're allowed to do a little peacocking

"Ladies Day brings in more of an overall effort," explains Manners of the subtle differences in dress you'll see on Wednesday, "but then again we wouldn't be female if we didn't want to peacock a little." While a drastic change in attitude would contradict the general no-nonsense look, adding a hat with a feather, a more colourful coat or a pretty dress like Manner's Ghost choice (below) will offer the desired sense of occassion.        

ghost dress

Delaney dress, Ghost, £82.50

A cosy-but-interesting coat will make your look

"Cheltenham is all about the perfect over coat," says Manners, "it must be feminine, flattering and beautiful or interesting in some way. One way to tick these boxes is to focus on finding a fun yet chic-silhouetted coat." She points to Burberry's double-breasted wool military coat as the perfect example of a Cheltenham-worthy style with its bell-sleeves adding a point of interest whilst still being capable of keeping racegoers warm out in the elements. 

burberry coat

Military coat, Burberry, £2,495


You needn't limit yourself to just one outerwear piece if the forecast is looking particular dire. “It's all about the layers, a stylish gilet under a tailored coat is a great option," say Thorogood and Turner. "Remember, it can be warm inside so you still want to look the part once you take your coat off."

mulberry coat

Belted coat, £895, Mulberry

Manners also says everywhere from Zara to Max Mara does Cheltenham-worthy toppers but if you really want to nail the look she recommends eschewing the shops altogether. "In my opinion, vintage is always lovely to wear to a day like Cheltenham- I usually raid my Mother's coat selection," she admits, an especially useful tip to keep in budget if you're attending more than one day.

farlows tweed jacket

Dubarry tweed blazer, Farlows, £227.40 

Don't worry too much about a hat

Many of us will think races and assume hats are de rigeur but at Cheltenham the attitude is more relaxed. "I love that you don't feel obliged to wear a hat and can be just as stylish and smart without one," says Manners.

Kate Middleton attending Cheltenham in 2007
Kate Middleton attending Cheltenham in 2007 CREDIT: REX

Back to that practicality point, a hat might be useful for pure keeping warm purposes though. A scan through the Duchess of Cambridge's previous Cheltenham appearences shows that anything from a fedora or beret to a cosy fur hat  goes.

"A Fedora hat is a must for keeping hair in check whatever the weather bringsWe complete our look with a different colour fedora each day, from a classic brown one day to a slightly more unique maroon colour the next,” say Thorogood and Turner.