Racing Fashion

The Lady’s Maid’s Guide to Style for The Cheltenham Festival

This week our Lady’s Maid, Alicia Healey, brings you ideas of what to wear to the races...

When you think of hats and horses, Royal Ascot might be the first event that springs to mind – a week in June that is as synonymous with style as it is with all things equine. March sees a very different racing event in terms of fashion: the Cheltenham Festival (13–16 March), the most prestigious meeting held at the Cheltenham racecourse, and the first notable event of the English racing calendar. Whilst the outfits of attendees are not quite so dressy as those at Ascot, it is still a place to show off your best country attire. Held in March, the weather usually calls for more practical winter wear – hats are worn but tend to be primarily for reasons of warmth as well as style, and are not obligatory; felt fedoras or berets are more appropriate than flamboyant fascinators.

The royals are the best models for inspiration when it comes to dressing for the races. They are usually dressed in an array of neutral earthy tones for winter races. The best colours to wear for Cheltenham are autumnal shades, perhaps with a little pheasant feather flourish on the hat in keeping with the country feel. As for the outfit itself, smart country wear is the aim: tailored tweeds, houndstooth, skirts in countrified colours, rather than rainbow brights. As an outdoor event your outerwear will be kept on most of the time, so pick a smart longline tailored coat with simple separates underneath. For footwear, leather boots with a block or flat heel are advisable over stilettos; there is a wide variety of stylish leather and suede boots at Fairfax & Favor, some with elegant heels suitable for smarter ensembles. English weather in March is unpredictable so a scarf and gloves are also advisable; a patterned silk scarf or faux fur collar are stylish ways to add warmth to your outfit. 

I’ve styled five possible outfits for Cheltenham below. The hat is the best signifier of how smart the look is. The first look is a fairly casual sweater and skirt ensemble topped off with a fedora hat; the last outfit features a chic silk trimmed occasion hat from Jane Taylor London. This would be more suited to Ladies day at Cheltenham, held on the second day, Wednesday 14th March – this is the day when you will see dressier outfits, more colour and flamboyant headwear, and where there is also a competition for the best dressed lady, known as #ColourMeMarch, to add a bit of fun to the style stakes!

Clockwise from bottom left: brown wool midi skirt: Joseph; smoky quartz drop earrings: Kiki McDonough; blossom check wrap: Really Wild Clothing; “Neptune” beret hat with pheasant feather trim: Rosie Olivia Millinery; white cashmere polo neck: N.Peal; “Regina” mahogany boots: Fairfax and Favor; brown leather Half Moon snakeskin-effect cross-body bag: A.P.C; tweed jacket: Dubarry of Ireland.

Clockwise from bottom left: “Soraya” coat: Hobbs; “Amberley” leather satchel in oxblood: Mulberry; Cashmere turtle neck jumper in bottle green: Really Wild Clothing; “Emma” leather gloves: Dents; “Suffolk” fedora in maroon with guinea feather wrap: Hicks and Brown; Mother of pearl drop earrings: Kendra Scott; Silk scarf: Aspinal of London; Suede over-the-knee boots: Gianvito Rossi; Houndstooth check midi skirt: Luisa Beccaria.

Clockwise from bottom left: block heel leather boots: Loro Piana; faux fur trim collar: Troy of London; leaf stud diamond and gold earrings: Anne Sisteron; “Provincial Lady” tweed hat: Lock & Co. Hatters; brown leather gloves: Dents; brown suede clutch: Peter Kaiser; dusty pink coat: Damsel in a Dress.

Clockwise from bottom left: black suede long boots: Russell & Bromley; beret hat in emerald green: Camilla Rose Millinery; faux fur trim gloves: Reiss; “Franklin” emerald green coat: Katharine Hooker; mini hat box bag: Aspinal of London; emerald leaf earrings: Anne Sisteron; black faux fur collar: Troy of London.

Clockwise from top left: “Citron” hat: Jane Taylor London; Toscana Lima coat in navy: Joseph; blue lace agate earrings: Monica Vinader; navy knitted dress: Altuzarra; grey suede clutch: L. K. Bennett; blue cashmere and silk scarf: Katharine Hooker; grey suede boots: Gianvito Rossi.

Alicia Healey is a former royal lady’s maid and author of “Wardrobe Wisdom”, due to be published with The National Trust in September 2018. You can follow The Lady’s Maid’s Looks and get more of her top tips on Instagram and Twitter @theladysmaid and www.theladysmaid.com

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