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What to Wear at Cheltenham Races

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Cheltenham Festival; the social highlight of the spring season. After a long cold winter, Cheltenham comes at a time when the sun begins to stay up longer, the daffodils make a break through and the temperature begins to rise. It’s the time of year where the summer colours begin to crawl out from the back of the wardrobe to see the light once more – it’s also a time where we can get away with adding a dash of ‘new’ into our lives. Cheltenham is not only a time to be social, but also a time where we can celebrate that summer is well and truly in sight.

In the spring like spirit, we’re lending a helping hand to spark a few ideas for that all-important ‘Cheltenham look’ – A great starting point is tweed. Tweed is must-have for a festival like this one; it oozes sophistication, class and most importantly takes the edge off the spring breeze – hold your horses it’s not summer just yet!

Race days are tradition to many people, especially for family time that feels more of an occasion than other gatherings. Following Covid, many of us are excited to get back to doing the things we love and that includes the races for lots of us! With the tickets booked and travel arranged, now it’s time to turn your attention to your outfit.

Ladies Fedora Hat

The main trouble with dressing for the races is finding that fine line between comfort and style. However, as countryside folk, we know that it’s easily achievable with a few key pieces. Think of it as regular country fashion but elevated a little. The overall look we’re going for is dressy but not formal; after all, it’s not a black tie event. You also need to think about the weather in typical British fashion. This is where your jacket or coat and footwear come into play.

With the Cheltenham Festival coming up this week, it’s definitely a hot topic right now! Whilst they do not have a dress code, we still think it’s best to still dress up if you can. Going to the races in a pair of jeans just seems so wrong! Below, you’ll find a handful of dressier items that you can wear for a race day, not just at Cheltenham but at various points over the spring and summer.

A collared shirt

Men - There’s nothing smarter than a collared shirt. Even if it’s worn with jeans, it still makes you look put-together! As country gentlemen, there’s a strong chance that you own at least one, if not multiple, collared shirts, probably a mixture of neutrals, checks and patterns. If you find an item that fits well and is good quality, why not buy it in every colour and pattern?

Ladies Tweed Outfit

The more formal the occasion, the more neutral your shirt should be. A simple country checked shirt is a great option for race day as it means you can wear some colour without it being too overpowering. In our collection, there is pretty much every colour under the sun in there so you’re sure to find a colour to match your suit.

Ladies - They’re not just for men, you know? A classic, fitted shirt will be an item you continuously go back to as it’s so versatile. On race day, you can pair it with any skirt or pair of trousers but also dress it down with jeans and canvas shoes for running errands during the daytime. Whilst you can go for an oversized look, collared shirts look better when fitted but not tight. An oversized shirt can look figureless whereas a tight shirt will look just as unflattering and likely to pop open!

When it comes to pattern, your choices are endless. Checks, stripes and prints adorn our collared shirt collection in multiple colours too. Just be sure that your shirt and the rest of your outfit don’t clash. Try to keep within the same colour family so your shirt blends rather than stands out. Alternatively, if you’re wearing alongside neutral block colours, a bolder shirt will be the focal point of your ensemble.

Tweed Blazers

Tweed suit pieces

Men - A tweed suit is a staple for countryside gentlemen, even if you don’t get to wear it too often. Here is where you’re best to keep it as classic as possible with a blazer and a waistcoat. Even the tweed blazer alone is a feature piece of any outfit. Paired with a collared shirt, you can wear most trousers and look super smart. For race days, a suit trouser or a pair of chinos should be dressy enough. For casual nights out, you can switch those for a pair of straight leg jeans!

If you really want to go all out, a pair of tweed shooting breeks really finish off the look. Don’t forget to match up your tweed because mixing up your tweeds is not a good look.

Ladies - If you’re a true country lady, you’ll probably have one of these in your wardrobe already! With our collection covering skirts, waistcoats and blazers, you can decide how many pieces you want to wear at once. We’re a big fan of wearing the skirt with either the waistcoat or blazer or switching the skirt for a pair of plain, fitted trousers. Wearing it as a three piece suit also looks chic so whilst it can be an investment outfit, you have lots of options in how to wear these three pieces. It should be noted that you should always wear the same tweed for all three pieces as playing the tweed mix and match game doesn’t look quite as good!

Ladies Tweed Ponhco

However you wear it, it will look classy with a collared shirt. This ensemble will never go out of style, no matter which country event you’re attending. Try matching the check in your shirt to one of the threads running through your tweed to really tie it all together.

Practical shoes

Men - Your go-to smart shoe should always be a leather brogue. They’re the perfect partner for any suit and are comfortable. They’re also easy to clean after a race day! Whether you go for a sleeker style or something with a grippier tread is up to you. If you wear them mostly for indoor events, a flat style is better for you. However, if you’ve got a summer of outdoor events to attend, think about getting a pair with a sturdy sole so you don’t slip on any mud!

Ladies - Many who don’t wear practical shoes to race days tend to not be very stable on your feet. As countryside fashion is a mix of practicality and style, you’ll know that you’ll be stood up most of the day and on grass. That means stiletto heels are out and easy to clean leather footwear is in. Riding boots, heeled ankle boots and country boots are the overall vibe we’re going for here. Whilst they might not be the most formal of footwear options, they are comfortable whilst still being stylish.

Ladies Tweed Skirt

A poncho (for the ladies)

If you’ve gone down the dress route for race day, be aware that it might get chilly. British weather can be unpredictable, especially coming into the spring months, so a cover up won’t go amiss for outdoor events. A poncho is the perfect mix of warmth and fashion and is sure to catch people’s eyes. You can also wear it over a tweed suit but again, make sure to match up the tweed first. The faux fur collar looks so luxurious too so keeping warm has never looked so good!

Race days don’t have to mean investing in a brand new outfit that you’ll never wear again. Countryside folk know how to dress up with existing pieces because they buy quality, versatile items and look after them properly. Now you’ve got your outfit planned, it’s time to get out there and place your bets!

Not heading to the Cheltenham Festival this year? Fear not, our hand-selected collection will be a great addition to kick starting your spring wardrobe. Shop Now >

Don’t worry, we haven’t forgotten you dapper chaps getting in the racing spirit! We’ve put together a hand-selected collection just for you. From tweeds to checks, there is something to add that spring to your step whether it’s Cheltenham we go to or off on a good old jolly. Shop Now >

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