Cheltenham Races Outfit Inspiration

4th March 2020 by

Cheltenham Festival 2020 is fast approaching, so it’s time to pick out your outfit for this eagerly anticipated event. Officially, there is no dress code for the races, however smart is preferable and most of us like to dress to impress. So why not grab some outfit inspiration and maybe even purchase that tweed jacket or that pair of boots you’ve been eyeing up for the last month?

The Festival

Cheltenham Festival is presented over four days, from March 10th - March 13th and is held at Cheltenham Racecourse. We hope you’re prepared for an exciting schedule of the very best jump racing as exceptional horses and jockeys race for the highest racing honours. Below you can find an overview of the 4-day event, and then we can jump right into fashion and style tips to set you apart from the rest!


Day 1 (10th March) - Champion Day

Day 2 (11th March) - Ladies Day

Day 3 (12th March) - St Patrick’s Thursday

Day 4 (13th March) - Gold Cup Day

Inspiration for the Women at Cheltenham Festival

We can proudly say that women have set the bar quite high when it comes to racecourse styles in recent years. Let’s take a look at the Duchess of Cambridge, Kate Middleton, for example. Knee-high boots, a stylish hat, gloves and a statement coat seem to be her go-to, this is the perfect combination if you’re looking to have a power outfit and keep warm at the same time. We all know March can be a bit chilly - make sure your outfit accommodates the weather!

Earthy tones seem to be the winner each year Cheltenham races roll around. They have become a trend lately, and with tones incorporated into designs that really make it pop, we’re not surprised they’ve weaved their way into various spring collection releases. It is important to note, avoid primary colours and especially the colour black. Stick with what you know and what matches the season, just simply add your own twist – navy blues, mustards, browns, caramels etc.

We’ve handpicked a few outfits to help you get started…

Ladies Outfit 1

                                                                             Ladies Outfit 1

For the jacket, we have the Anna Lascata Alexandra Jacket in Worsted Tweed. The Alexandra Jacket is an elegant and timeless, three quarter length style jacket. It is made from 100% Donegal tweed which will keep you warm but also smart. To pair with the jacket we have chosen the Dubarry Chamomile Shirt in White, this shirt is a traditional style, with a ruffle detail along the buttons and a high neck collar. The Chamomile shirt looks great with the Elizabeth Skirt in Worsted Twist, and the skirt also matches the jacket for an outstanding outfit.

No outfit is complete without those essential accessories! Not only do those accessories finish off your outfit, they are also very good at keeping warm, we all know how cold Cheltenham racecourse can be! The Dubarry Kilconnel gloves are the perfect solution for keeping your hands warm as they are lined with a cashmere blend. The last thing to finish off your Cheltenham outfit has to be a hat, we think the ideal hat for this is the Hicks & Brown Suffolk Fedora Hat with the Pheasant Feather wrap detail. You may remember that at the beginning of the year Kate Middleton was seen in this classic, stylish hat, and we think you will agree it finishes off any outfit.

                                                                                              Kate Middleton in Hicks & Brown Hat

When deciding what footwear to wear for Cheltenham, you need to think about comfort! We all know that Cheltenham races can be a long day on your feet, so we think the Fairfax & Favor Heeled Regina is the perfect boot. The Heeled Regina has a 5cm cuban heel, so it gives you that bit of height without being an uncomfortable heel. This boot is available in 5 different colours in the suede, and also a mahogany leather. For this outfit, we have chosen the Heeled Regina in Chocolate as it complimented the tweed and hat.

Ladies Outfit 2

On to outfit number 2 for the ladies, we feel this outfit is perfect for the ladies amongst us that don’t like wearing skirts, pairing a jacket with a pair of jeans, you can still achieve the ultimate racing look.

                                                                                      Ladies Outfit 2

The Welligogs Westminster Jacket is a beautiful brown checked tweed, made from 80% wool. This jacket has an understated check ensuring you can match it with most colours. We think the shirt most suited to this outfit is the Dubarry Snowdrop Shirt in White. The Snowdrop shirt is a classic shirt and it can be paired with most outfits to give you a sophisticated look. For this outfit instead of choosing a skirt, we have chosen the Schoffel Cheltenham Jeans in Navy, we know that skirts aren’t for everyone. The Schoffel Cheltenham Jean is made from stretch cotton which gives these jeans a flattering fit. 

Now, no outfit is complete without a handbag! Our favourite here at Allcocks Country is the Fairfax & Favor Windsor in Tan, this handbag is large enough for all those essentials when you're out for the day. The Windsor is made from the finest suede and leather, it also includes an interchangeable tassel enabling you to match the tassel to your outfit.

We finish the outfit off with a pair of boots, we think the boots that compliment this outfit are the Fairfax & Favor Amira Boots in Tan, they are crafted in suede, with a leather lining to provide you with ultimate comfort. We think you would agree that these boots are definitely a head-turner. The 7cm thick cuban heel will make sure you’re walking tall, whatever the occasion.

Inspiration for the gentlemen heading to Cheltenham Races

Gentlemen, it’s your time to shine at the Cheltenham Festival. It is the perfect opportunity for not only women, but men to showcase their personal style. There are no rules when it comes to men’s racing fashion, but it is expected that you make an effort and look smart, so we are here to help you out. You need to stand out from the crowd with something different other than a black and white suit!

Gentlemen’s outfit 1

                                                                                           Gentlemen's Outfit 1

We’ll start things off with the Laksen Sologne Dress Vest in Heather, this waistcoat is made from Loden wool, it is lightweight and soft to touch, its a smart touch to any outfit. This dress vest is beautifully tailored and really shows off your style. 

When you are at any country event you always see a variety of checked shirts. For this outfit, to pair with the Laksen Dress Vest we have chosen the Schoffel Brancaster Shirt in Purple, we think the check of this shirt matches with the dress vest. The Brancaster is 100% cotton which makes it a lightweight and breathable shirt for all seasons.

The Schoffel Canterbury Jeans in Camel are a popular colour choice, which works with pretty much any outfit. These jeans are comfortable so are ideal for a day at Cheltenham races. The Canterbury Jeans are of the highest quality, so there is no doubt that they should be part of your outfit for any occasion.

For the footwear we have chosen the Dubarry Antrim Boots in Bourbon, these boots are GORE-TEX lined so completely waterproof, making them the perfect boot for a wet day at Cheltenham Races! These boots are also smart so are ideal for those wet, muddy occasions but where you need to remain smart.

As for accessories for men, they don’t often wear hats, but if you do see a gentleman in a hat, it’s sure to be the peaky blinders style hat! So rather than focus on headwear for this outfit, we have focused more on accessories for the stylish man. The Laksen Paisley Ascot completes this outfit we think, it is made from 100% silk, and it is soft.

Gentleman’s outfit 2

                                                                                              Gentlemen's outfit 2

There’s a wealth of choice for the stylish men, and if you’re looking for something in traditional tweed, we’ve got you covered. It is essential, however, to get the basics right.

For this outfit again we have chosen the Schoffel Canterbury Jeans in Navy, as they are smart looking jeans that can be worn for many occasions.

The shirt is the Alan Paine Ilkley Shirt in red check, it is crafted from soft, pure cotton fabric, ensuring it is comfortable to wear. For the second layer, in case you have to battle the rain or cold temperatures, be sure to pick up the Schoffel Oakham Fleece Gilet in Navy. It’s a cosy and also quick drying gilet, designed to be used as a mid-layer for extra warmth. It’s one of the most popular products within the Schoffel clothing range, and we can see why - available in 10 colours.

The final layer, includes the traditional Alan Paine Combrook Tweed Blazer in Sage. It provides a classic fit and is crafted from 100% tweed wool. This smart blazer is designed for sporting events like Cheltenham Races.

Finally, it’s the all important footwear. The Dubarry Kerry Boots in Walnut are the ideal boots for this outfit, they are GORE-TEX lined, making them completely waterproof to protect you from the elements. These boots also feature Dubarry’s water-resistant DryFast-DrySoft leather, so if it is raining the leather will dry quickly but also remain supple. The soles have a thermal lining for warmth and extra cushioning for comfort.

If you have been inspired by any of the products above or would like some more information on the wide range of products we stock then please call us on 01299 822 212 or email

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