What to wear to the Cheltenham Festival

SoGlos shares some top tips on what to wear to the races this March 2024, with Cheltenham Festival fashion partner, Jade Holland Cooper, providing the lowdown on everything from her must-haves to her no-go's.

By Chloe Gorman  |  Published
Style ambassadors, Rosie Tapner and Frankie Foster, share their festival fashion must-haves, from comfy shoes and a warm coat to a stylish fedora or flat cap.

As well as being the highlight of the jump racing calendar, the Cheltenham Festival is a big day for fashion fans, too.

With stylish racegoers showcasing a range of looks from classic Tweeds to fancy fascinators, SoGlos shares fashion advice from both Cheltenham Racecourse's official fashion partner, Holland Cooper, and The Jockey Club's style partner, House of Cavani, on what to wear to this year's event, to make sure you look and feel fabulous for your day at the races. 

Unlike tips from the bookies, these helpful hints will come in handy of the course, especially on Style Wednesday, as the inaugural Slow Fashion Awards offers the chance to win a Boodles necklace — worth £4,000 — to those who best style vintage and borrowed pieces.

About the partners – Holland Cooper and House of Cavani

Fashion designer and entrepreneur, Jade Holland Cooper, is once again acting as the official fashion partner of Cheltenham Festival 2024, with her brand providing staple pieces for a stunning spectating outfit.

Founder of Holland Cooper, a hugely successful label that turned over more than £26 million in 2023, Jade is also a horse lover — with her collections always featuring a clear nod to countryside, from chic tailoring to sophisticated bags and millinery.

Long-term style partner of the Festival, House of Cavani offers contemporary formalwear fit for the finest names at the races — with loyal fans including Love Island star-turned-pundit Chris Hughes and ex-footballer Michael Owen.

Festival-goers can now take advantage of 15 per cent off their House of Cavani order by using an exclusive code found on the Jockey Club website.

When it comes to Cheltenham Festival Fashion, what are the staple pieces worth investing in?

Rosie: My favourite thing about the Cheltenham Festival style is that it’s very much up to the individual and how they like to dress. And it’s timeless. So if you’ve been before, you’ve probably got the perfect outfit tucked away in your wardrobe.

Comfort comes before anything. No stilettos or super-high heeled shoes. I’d opt for a long boot, either flat or with a small heel. With hats, the fedora is the perfect choice. It’s classic, warm and far less likely to blow away than a big fancy hat!

Frankie: I really think a smart overcoat makes almost any outfit look instantly smarter. You can wear one over stuff you already have, they will last for years and keep you warm so it’s a worthwhile investment. Bar the obvious: comfy shoes as you will put in some miles, and for me personally I like a nice tie that stands out.

What are your Festival must-haves?

Frankie: You will rarely look smarter than when you are wearing a good suit. 

Otherwise simply be smart, be comfortable, be warm, and maybe wear one thing that makes it feel more ‘racing’ or more ‘Cheltenham’. Even some lucky socks or cufflinks could do.

Rosie: For me, number one is a warm, heavy coat and layers. Cheltenham Festival is so much fun but you need that coat in the Cheltenham cold.

The right shoes. Sturdy, comfy, all weather boots for me. You don’t want to be with your friends complaining about your feet hurting all day!

A good bag! This is actually quite underrated. But a good bag that’s not too big to carry your essentials like your phone, your race card - any money that you might win! - and some extra layers. I always have a scarf and some blister plasters just in case.

What about hats? 

Rosie: For me, it’s something smart and understated. And something very country! You don’t need anything particularly fancy at Cheltenham at all. I love a simple fedora with some feathers.

This year, I think we’ll be seeing a lot more headbands. They’re super easy to wear, keep your hair out of your face and are less likely to blow away if it’s windy so I’m all for the headband! And you can get really lovely ones with feathers and all sorts which end up looking like a beautiful hat but much easier to wear.

Frankie: For me it’s all about a flat cap. A navy will be most versatile and a give you a smarter look (if its waterproof, even better). A Tweed flat cap is more National Hunt, and more Cheltenham, but it’s a little harder to match – you’d probably want to be wearing tweed or similar colours.

What fashion advice would you give to first-time festivalgoers?

Rosie: It’s unlike any other festival. It’s extremely inclusive when it comes to style so you never have to worry about if you’ve got the dress code right. 

A smart pair of trousers, some long boots, a nice jumper - I always go for a roll neck jumper - a tweed jacket and finally top it off with a hat. But most of all, dress for the weather! It can be cold at Cheltenham and there’s nothing worse than having to sit inside all day because you didn’t layer up.

Frankie: My advice for first timers is to use what you already have and then add a little bit of a 'Cheltenham' accessory. Most blokes have either a suit at home, or some form of trouser/shirt/jacket that works. From there your proper National Hunt accessory is a flat cap but my favourite investment is a new tie. A new tie can make an old suit feel like a new one. How often do you get complimented on your hat? Coat? Shoes? You will on a good tie!

Are there any absolute no-no's when dressing for Cheltenham Festival?

Rosie: This is quite an obvious one but I’m going to say it anyway: Stilettos.

Another one, light and airy dresses. It’s the middle of March and though it can be warm at Cheltenham it’s probably going to be a few degrees colder than everywhere else. So no light and airy dresses that might float up! And I’d always have tights on because my other fashion no-go is bare legs. Tights, trousers, you can wear a skirt but nothing too short. You want to be classy at Cheltenham. Plus, if it’s windy there’s nothing worse to be wearing than a short skirt.

Frankie: Maybe I am stating the obvious again but two things spring to mind. One: Wear what fits! Your nicest jacket that doesn't fit will look worse than something that does.

Two: Test run the new shoes! Blisters put a damper on the day and slow you down. By all means buy a nice new pair of shoes, but wear them in. I have made this mistake and your friends don't want to piggyback you home! 

What are your go-to pieces for a day at the races?

Rosie: For me it’s all about the tweed, a splash of colour and layers. Paired with a comfy pair of boots and a nice hat. I’m a country girl at heart so Cheltenham is perfect for my style! It’s all about country wear and combining style with comfort.

Frankie: I love putting on a suit and a big day out at Cheltenham is prime for it. My go to for the festival is always a suit with a long overcoat on top. A dark navy overcoat will be most versatile and go with practically any suit and tie.

Something I like to do when it’s cold but a bit of sun poking through is wear the suit trousers and waistcoat, without the suit jacket, but with a smart overcoat. You are warm enough without feeling like you can’t move in too many layers, you just have to be brave enough to rock the shirt and waistcoat in a bar later on without looking like a waiter!

What does Cheltenham Festival style mean to you?

Rosie: It means classy, warm, comfortable and most of all being yourself. One thing about the Cheltenham Festival is that it’s for everyone. You don’t have to fall into a dress code and be the same as everyone else, you can very much make it your own. So turn up, be comfy, be yourself, be warm and enjoy yourself!

Frankie: Look and feel smart. Wear something that’s a little ‘different’, you are not off to work! And enjoy it. I absolutely love the feeling on raceday as you leave the house dressed up, cash in your pocket, and a big day of racing ahead!

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