The Ultimate Cheltenham Festival Style Guide with Welligogs and The Cotswold Hat Club
Cheltenham Festival is not just the pinnacle of British horse racing; it is also one of the most photographed style moments of the British social calendar. Across four exhilarating days, women arrive in sharp tailoring, heritage textures, practical elegance, and statement accessories that work just as well in the grandstand as they do strolling between enclosures.
This is where Welligogs and The Cotswold Hat Club come together. Both brands are rooted in British craftsmanship, countryside sophistication, and clothing that performs as beautifully as it looks. This collaborative guide brings you race-day outfits that balance style, comfort, and seasonal practicality, so you feel confident from the first race to the final toast of the evening.
What to Wear to Cheltenham Festival
Cheltenham style sits between refined racewear and polished country chic. The weather in March is famously unpredictable, which makes layering, quality fabrics, and structured outerwear essential. The look should feel smart without being stiff, feminine without being fragile, and practical without losing elegance.
Hats are a defining part of the experience. A beautifully shaped felt or wool hat elevates even the simplest outfit, giving it that unmistakable Cheltenham finish. This is why pairing Welligogs’ tailored pieces with The Cotswold Hat Club’s heritage headwear creates outfits that look effortless yet intentional.
Outfit for the Races
Race day calls for timeless elegance with movement and comfort. The Electra hat features a silk rust orange base with a striking spray of orange and brown feathers and quill. This hat brings classic racing glamour with a sculpted silhouette that frames the face beautifully, making it perfect for photographs and grandstand moments.
The Kate White Shirt creates a crisp foundation, while the Montana Long Skirt adds flowing sophistication and protects against cool spring winds. Together, they strike the ideal balance between tailored and relaxed. The Beth Tan Boots offer the grip and comfort needed for grassy enclosures without sacrificing style, while the Phillipa Tan Bag ties the look together in rich heritage tones.
This outfit works because every piece serves a purpose: the skirt moves easily as you walk, the boots provide stability, and the hat gives your look unmistakable race-day polish.
Outfit for Afternoon Tea
After the excitement of the races, afternoon tea is a moment to relax without losing your sense of style. The Andromache Hat is perfect for this affair, a Petrol teal blue felt beret with petals and veiling offers an understated elegance, ideal for intimate tables and champagne moments.
The Knightsbridge Mist jacket brings Welligogs’ signature tailoring into a lighter, more relaxed setting, layering beautifully over a simple top. Nina Navy Jeans keep the outfit grounded and comfortable, while Hackney Navy Suede Loafers add refinement without feeling formal. The Lion Navy Belt completes the look with a subtle nod to British heritage.
This is an outfit designed for versatility, smart enough for a grand hotel lounge, relaxed enough for a long afternoon of conversation and indulgence.
Outfit for Browsing the Shops
Cheltenham’s shopping villages and pop-up boutiques are part of the festival experience. Comfort matters, but style still counts. The Ophir hat comes in a leopard print. This teardrop felt hat with a leopard print bow is effortlessly wearable, adding character without feeling heavy or too formal.
Layer the Cassandra White Shirt under the Demelza Coffee for warmth and texture. Nina Wheat Jeans Keep the look light and fresh, ideal for daytime wandering. Paired again with the Beth Tan Boots you get all-day comfort with a smart, cohesive finish.
This combination is practical, flattering, and easy to wear, allowing you to move freely while still looking considered and put together.
Outfit for Evening Drinks
As the sun sets, Cheltenham takes on a richer, more glamorous mood. The Beverly deep burgundy felt hat, fixed with a spray of rare breed feathers, adds drama and evening-ready elegance, elevating your outfit without feeling excessive.
The Madeira Velvet Jacket introduces depth and softness, reflecting evening light beautifully. Paired with Icon White High Waisted Jeans the look stays modern and flattering. Hackney Burgundy Suede Loafers add colour and luxury, creating a seamless transition from day to night.
This outfit is ideal for cocktails, dinners, and celebratory moments, proving that race-day style does not have to stop when the last horse crosses the line.
Confidence, Craftsmanship, and Timeless Race-Day Style
Cheltenham Festival is about more than racing, it is about tradition, confidence, and celebrating British style at its finest. By combining Welligogs’ beautifully crafted clothing with The Cotswold Hat Club’s heritage hats, you create outfits that feel authentic, flattering, and built for real-world wear.
Every piece in this guide is designed to last beyond a single event, giving you wardrobe staples that work season after season. Whether you are dressing for the excitement of the races, a relaxed afternoon, or elegant evening drinks, these combinations help you look and feel your best.
Explore the latest collections from Welligogs and The Cotswold Hat Club and discover race-day style that feels as confident as it looks.
Final Thoughts
Cheltenham Festival is one of those rare occasions where fashion, heritage, and atmosphere come together in a way that feels truly special. Dressing well here is not about following trends, but about choosing pieces that reflect confidence, craftsmanship, and a distinctly British sense of style. When your outfit is thoughtfully put together, it enhances the entire experience from the thrill of the first race to the last glass of champagne in the evening.
By pairing Welligogs’ beautifully cut clothing with the characterful hats from The Cotswold Hat Club, you create looks that feel timeless yet current, polished yet comfortable. Each outfit in this guide is designed to move with you throughout the day, adapt to changing weather, and still look elegant in every setting Cheltenham offers.
Whether you are attending for the racing, the social scene, or simply the spectacle, investing in quality pieces means you are not just dressing for one festival; you are building a wardrobe of enduring British style that will serve you season after season.
Frequently Asked Questions – Cheltenham Festival Style
What is the dress code for the Cheltenham Festival?
Cheltenham does not enforce a strict dress code, but the social expectation is for attire to be smart, polished, and well-put-together. British racegoers typically wear tailored coats, structured jackets, quality boots or loafers, and a statement hat. Casual trainers, hoodies, and overly relaxed clothing look out of place.
Do women have to wear hats at Cheltenham?
Hats are not compulsory, but they are strongly associated with Cheltenham’s heritage style. A well-chosen felt or wool hat instantly elevates your outfit and helps it feel race appropriate. This is why pieces like the Electra, Andromache, and Beverly work so well across different parts of the day.
What shoes are best for the Cheltenham Festival?
Block-heeled boots, smart flats, or suede loafers are the safest options. Much of Cheltenham involves walking on grass, gravel, and uneven paths, so stilettos and thin heels are risky. Styles like the Beth Tan Boots or Hackney Suede Loafers provide stability without compromising elegance.
How do you dress for unpredictable March weather at Cheltenham?
Layering is essential. A structured jacket or knit over a crisp shirt allows you to adjust throughout the day. Long skirts, tailored jeans, and boots protect against wind and cold while keeping the silhouette refined. Hats also add warmth as well as style.
Can you wear jeans for the Cheltenham Festival?
Yes—when styled correctly. Dark or neutral high-waisted jeans paired with a tailored jacket, quality footwear, and a statement hat look completely appropriate. This is why outfits like the Knightsbridge Mist with Nina Navy Jeans work so well for afternoon tea and relaxed social moments.
How do I make my outfit look ‘race-day smart’ rather than casual?
Three elements matter most: structure, texture, and accessories. A tailored jacket or velvet top, heritage fabrics, and a hat immediately signal race-day dressing. Even simple jeans or shirts look elevated when paired with these pieces.
Is it better to dress for fashion or comfort at Cheltenham?
You need both. The day is long and involves a lot of walking, standing, and changing weather. The strongest Cheltenham outfits like those in this guide use premium fabrics, supportive footwear, and practical layers without sacrificing style.
Can one outfit work from day to night at Cheltenham?
Yes, if the base pieces are versatile. Switching to a velvet top, richer colours, or a more dramatic hat, like the Beverly, instantly transforms a daytime look into an evening-ready outfit without needing a full change.
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