The Cheltenham Festival is back, and it's even more stylish than last year. Racegoers head to the famous Cotswolds racetrack to enjoy a day of sports spectatorship, rocking an eclectic array of stylish outerwear in the process.
The royal family are regulars at the horse racing event and always look chic. Although there are no official style regulations for the festival, royal ladies from horse racing style veteran Zara Tindall to Queen Camilla never fail to make a statement in their attire.
British heritage style is a recurring theme, and no one knows this better than designer and creative director Amanda Wakeley OBE. Amanda has dressed many of the world's most stylish women, including the late Princess Diana, and exclusively gives Best Quality Designer Handbag readers an insight into modern race-day dressing.
"At Cheltenham, there aren't strict dress codes that you'd see at events like Royal Ascot, so the atmosphere allows a little more freedom," she explains. "That said, the royals tend to approach these occasions with an instinctive sense of polish. Someone like Zara Tindall dresses very much in tune with the setting, tailored coats, boots, and pieces that feel comfortable outdoors. While still maintaining that understated elegance, people associate with royal style."
Style rules embraced at Cheltenham
Tweed and wool are key
You will always see these two textures featured at Cheltenham. "Tweed and wool simply work in that environment, especially at the mercy of the English weather," Amanda explains.
"You're outside for most of the day, often in unpredictable March winds, so fabrics that offer warmth and structure make perfect sense," she notes. "They also feel completely at home in the rural backdrop. A great tweed coat or a beautifully cut wool piece carries heritage, yet when the tailoring feels sharp, it never looks dated."
A tailored turn
Tailored items are a fail-safe, classic option for any racegoer, but cuts have changed over time. "What I notice now involves a much cleaner approach to tailoring," Amanda remarks. "Women still embrace classic fabrics, yet the silhouette feels more streamlined and, at times, androgynous."
We often see the royal ladies opt for dress coats, which Amanda loves to see. "A long, tailored coat worn over belted wide-leg trousers and a neat polo neck mixes the masculine and feminine. It brings a contemporary edge to materials that traditionally belonged to country wardrobes, which keeps the whole outfit feeling fresh," she adds.
Relaxed yet respectful
Key horse racing events are Cheltenham and Royal Ascot, but there are definite differences between the two. "Cheltenham and Ascot have very different personalities," Amanda notes.
"Royal Ascot leans toward polished, formal dressing. Think beautiful dresses, precise millinery, and a very defined sense of occasion. Cheltenham feels far more relaxed and grounded in its countryside setting," she muses. "The focus shifts to strong outerwear, boots, and fabrics that make sense outdoors," she adds. "Headwear follows suit, of course, instead of the sculptural millinery you often see at Ascot, hats at Cheltenham tend toward felt trilbies or Baker Boy styles. The look still carries elegance, yet practicality sits much closer to the centre of the wardrobe."










