What to Wear to Cheltenham Festival: A Country Style Guide to Elegant & Practical Race Day Fashion

Cheltenham Festival is one of the most stylish events in the racing calendar, and when it comes to what to wear, it’s all about striking the perfect balance between elegance and practicality. With the unpredictable British weather in mind, choosing an outfit that’s both chic and functional is essential.

This year, I’ll be wearing the Dubarry Blackthorn Jacket with the matching Blackthorn skirt paired with the Dubarry Daffodil shirt for a classic, tailored look. I’ll accessorise with the Dubarry Monart saddle bag and a Hicks & Brown fedora and finish the outfit with classic black Fairfax & Favor Regina boots—the epitome of countryside luxury.

Dressing for the Weather: Versatile Outfit Choices:

While a skirt is a timeless option for race day, Cheltenham’s unpredictable weather means having a backup plan is always wise. If rain is on the cards, I’ll be swapping the skirt for white or black jeans, ensuring warmth and comfort without compromising on style. Layering is key, and the Dubarry Blackthorn jacket provides the perfect mix of structure and warmth while maintaining that quintessential country-chic aesthetic.

Alternative Cheltenham Festival Outfit Suggestions:

If you’re looking for inspiration, here are a few other outfit combinations that will keep you looking effortlessly stylish at Cheltenham:

• Tweed & Tailored Elegance– A well-fitted tweed blazer with a silk blouse, a structured midi skirt or fitted trousers, and knee-high boots. Brands like Holland Cooper, English Nettle and Dubarry offer excellent options. I am in love with this English Nettle Horton jacket, and it's next on my hit list of purchases!

• Statement Coat & Layering – A tailored wool coat in a bold hue over a knit dress or tailored trousers, finished with a structured handbag and knee-high boots.

• Dressing to Impress – Cheltenham’s Style Day is one of the festival’s biggest highlights, with racegoers pulling out all the stops in lavish outfits, statement hats, and luxurious accessories. From designer coats to bespoke millinery, it’s a chance to showcase countryside glamour at its finest. However, elegance doesn’t have to mean discomfort—choosing pieces that allow movement, warmth, and breathability is key to enjoying the day in style. An elegant dress, bright and colourful headwear, and heels are the chosen look for many; however, if you take this option, remember the unpredictable weather you may get on the day!

The Importance of Comfortable Footwear:

A day at Cheltenham means a lot of standing and walking, so comfortable footwear is non-negotiable. My go-to choice is the Fairfax & Favor Regina boots—stylish yet practical with their supportive fit and durable soles and a full range of colours, both seasonal and core lines. However, if the ground is wet, opting for well-proofed or waterproof boots is a must to stay comfortable throughout the day. Dubarry Galway boots are excellent options for navigating muddy areas while keeping your feet dry.

Final Tips for Cheltenham Festival Race Day Style

• Check the weather forecast before finalising your outfit.

• Layer smartly—a stylish scarf or a well-tailored jacket can make all the difference.

• Accessorise thoughtfully—a classic fedora or structured handbag adds instant sophistication.

• Prioritise comfort—from your footwear to your outerwear, ensure you’re warm and able to move freely.

With the right outfit, Cheltenham Festival is the perfect opportunity to showcase your countryside style with confidence. Whether you opt for a classic tweed look, a bold statement coat, or a chic dress with luxe accessories, the key is to dress for both the occasion and the elements. See you at the races!

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