(estimated 5 minute read time)

With events such as the Cheltenham Festival and Grand National taking place, we’re providing you racegoers with a helping hand when gearing up for a day at the winter races. Cheltenham and Aintree provide the perfect opportunity to showcase your sartorial prowess, despite the new relaxed rules which encourage you to come “dressed to feel your best”. Therefore, the only rules this year are no offensive fancy dress outfits and no team kits.

With the races being held at the end of the Winter season, the most important factor when thinking of your outfit is to ensure it’s weatherproof. The British weather, as we all know, is unpredictable so layering up is crucial. Thermal vests, gloves, trench coats and hats are all key accessories to consider to keep yourself warm.

These events showcase some of the world’s finest racing; therefore with the finest racing tends to come the finest fashion. Here is our ultimate guide to traditional racing fashion, designed to help you make a lasting impression at this year’s winter races.

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Ladies attire


The focal point of any winter racing outfit has to be the outerwear, whether that be a trench coat, blazer or a fitted coat.

When it comes to specifics, colour, fabric, and print are all key factors when choosing your garment. Bold colours are great for making a statement look, although it’s neutral earthy tones that dominate in the winter months. Autumnal colours along with tweed patterns are guaranteed to be most popular this year. No matter whether it’s plaid, barleycorn, herringbone, or houndstooth, tweed offers an effortlessly elegant country look, guaranteed to deliver both practicality and style.


For winter racing fashion, a stylish hat is a great addition to accentuate your outfit. The focus for headwear is to opt for functional yet stylish options like the fedora, trilby or beret, leaving the flamboyant fascinators for the summer months. For optimal comfort and warmth, choose hats made from high-quality materials like 100% wool with a luxurious satin lining.

The preferred colour palette includes darker tones such as black, navy, deep green, and burgundy, reflecting a timeless sophistication. Additionally, neutrals like camel, tawny, and taupe are excellent choices for a refined look. Let your headwear be a tasteful complement to the rich heritage and style that defines the racing experience.


Choosing the correct footwear on raceday is crucial; comfort is key – the last thing you want to do is cut your day short because your feet are sore or cold. Consider high-quality materials like leather or suede for durability and insulation, with leather being ideal for protection against the elements.

Classic styles such as knee-high or ankle boots offer versatility, pairing well with various outfits while providing necessary coverage. Whether you go for a chunky heel or flat is up to you, our advice would just be to stay away from the stilettos!

Darker tones like brown or black are practical choices that effortlessly blend with the festival’s atmosphere and mud-resistant functionality. Prioritise comfort without compromising on elegance, and your chosen boots will not only keep you warm but also contribute to a polished and functional festival look.


All that’s left to do is accessorise – and your options are endless. A key accessory, which we believe is a must have, is gloves, not only for warmth but the perfect way to finish off an outfit.  Enhance your race day experience by adding a cosy scarf for an extra layer as you cheer your horse past the winning post. Alternatively, opt for a silk scarf, Jade Holland Cooper’s fashion must-have, which offers the perfect pop of colour to complement your tweed ensemble and elevate your overall look.

A compact, small, leather bag, will make a stylish choice! The right bag can complement your outfit perfectly, especially with styles like croc-print, quilted, and chrome gaining popularity this winter season. Chain-adorned bags make for the perfect accessory which combines the bag and jewellery categories. And of course, don’t forget to bring an umbrella!

Men’s attire


A sophisticated country look is the go-to for most men attending the races this time of year. Similar to the women, a smart overcoat or blazer is the perfect piece to accompany a smart suit whilst also providing warmth and a timeless aesthetic. A good quality overcoat will last for years, so it’s a worthwhile investment and a great addition to your wardrobe. A three-piece suit continues to be a top choice for many racegoers with the waistcoat adding an extra layer of refinement. Paired with a sports coat or covert coat, it effortlessly pulls together a refined and polished overall look.


Fedoras and trilbies are also a great choice for men, adding a touch of classic charm to the race-day attire. However, the undeniable star of men’s headwear fashion is the flat cap. This quintessentially British accessory has become the most popular choice among gentlemen. Its versatility allows it to complement various outfits, whether paired with a tailored suit or more casual country attire.


Buying a fresh new pair of shoes is always a great feeling, but don’t forget to wear them in before the big day out! Blisters will put a damper on the day, so you want to make sure your shoes are stylish as well as comfortable. Chelsea boots tend to be popular at the races, especially if it’s predicted to be a rainy day. If the weather is due to hold up, then  a smart pair of Oxford shoes or brogues in brown would perfectly complement tweed or earthy colours.


When it comes to accessorising, this is the perfect opportunity to add some colour and character to your outfit. If you opt for the smart look then a tie is a great way to bring the outfit together. Cuff links, with their subtle yet distinctive designs,are also a great addition if you’re wearing a suit. Additionally, pocket squares offer a perfect opportunity to inject a pop of colour or a subtle pattern, enhancing the overall sartorial finesse.

This year Cheltenham Festival have introduced Style Wednesday, the new ‘Ladies’ Day’, which is a celebration of the glamour and glory that the festival has to offer. To commemorate 100 years of the Boodles Cheltenham Gold Cup, the festival has introduced The Slow Fashion Awards. These awards showcase the festival’s fabulous and timeless fashion while celebrating traditions and creating new ones. The Slow Fashion awards celebrate vintage and borrowed items, along with investment pieces which can be passed down through generations. Both men and women are invited to take part so if you’re attending on Style Wednesday this year, give your A game and you could be in with a chance of winning prizes including a Boodles pendant worth over £4,000.