Cheltenham Style Guide with Harriet Lily

Published : 03/03/2024 10:00:00
Categories : Latest News

Cheltenham Style Guide with Harriet Lily

Harriet Lily is a "Country Girl" in a Professional World. We love following her country style on insta and she always has time for really good styling tips!

So we’ve given Harriet the reins for today's feature and she chats about her style picks for the show season ahead and more specifically for Cheltenham. 

Cheltenham festival in March is one of the biggest events of the year, not just in the jump racing calendar, but as a general sporting spectacle. The event pulls in crowds of up to 75,000 on the Gold Cup finale day and consists of racegoers, celebrities and sporting legends. This year the Festival is celebrating 100 years of the Gold Cup, and the event promises to be bigger than ever. 

As with many other iconic races, the Cheltenham Festival is not just about horseracing. A huge part of the event is of course the fashion and personally, I often prefer people watching and outfit spotting at Cheltenham than I do watching the races! 

Although there is no formal dress code for Cheltenham races, the event is synonymous with British tailoring and tweed. It is often associated with a more luxurious, heritage style that is uniquely different to many other big racing events which are seen as more obviously glamorous. I think that’s probably why I love Cheltenham races more than any other, because the associated styling is so aligned with my own personal style – a mixture of quality classics, that can be worn time and time again, but with sharp tailoring that flatters you no matter how many layers you’re wearing! 

Make no mistake, come race week, Cheltenham will be a sea of tweed, with many racegoers emulating the iconic Cheltenham style. So the question is, if you are attending the races this year, how do you stand out from such a large tweed-wearing crowd?! 

Here are some of my top tips and picks… 

Your Style

I think first and foremost it’s worth stating the obvious – you should absolutely wear whatever you feel most comfortable in. I think many people fall foul of trying to fit into a particular aesthetic and I can honestly say in years gone by, I have been one of those people. However, as I get older and more comfortable with my personal style, my biggest piece of advice is go dressed as YOU. Do not try to be someone or something else – it’s great to look at others for inspiration (I do this all the time), but I stay fundamentally true to my style. The best way to do this is to follow these golden rules:

  • Wear shapes, sizes and fabrics that you would typically wear and you know work well for you
  • Choose items of clothing and accessories that make YOU happy 
  • Take inspiration from others, but if you end up in an outfit that looks 99% different from the rest of your wardrobe – rethink your choice as you’ll be questioning yourself all day and not enjoying the races.

With the most obvious thing out of the way, below are my top tips for Cheltenham dressing.

Layers are your best friend!

The weather is so unpredictable during Cheltenham Festival week that you may get snow, rain, wind, sunshine or a mixture of all of the above on race day (and trust me, there have been occasions where I’ve experienced this!). The chances are, you’ll be outside for a lot of the day, but there are also opportunities to spend time inside (and with so many spectators in the same place, it soon gets toasty warm!) For guaranteed comfort all day, make sure your outfit consists of layers. My go to is a thin base layer, something like a fine roll neck, which can be paired with a thicker jumper, or worn alone under a coat. 

Outerwear is the star of the show

There’s a reason Cheltenham is known for tweed – you’ll be wearing a coat pretty much all day, so it needs to be a good one! The chances are, it’s going to cover the rest of your outfit, unless you are particularly daring or hot-blooded! For the next two years, Holland Cooper are officially fashion partners of Cheltenham races and I have to admit, there are no better tweed tailoring options than Holland Cooper for the perfect Cheltenham look. My personal favourite is a tailored trench coat – it’s an iconic look and one that is instantly recognizable as Cheltenham style. However, I appreciate this look is not for everyone (style or budget), so I would suggest you pick a statement coat (tweed or not), that suits your style – anything from a cape coat, a blazer or even a long overcoat will fit right in, so long as you feel good in it!

Accessories make the outfit

Never has a statement been truer than dressing for Cheltenham races! You’ll be covered up for most of the day, so to stand out and make your outfit more unique my top tip is to make the most of accessory options. And there’s so many options! This is what I would choose:

Jewellery – Of course, we have to talk about jewellery! It’s always the thing that dresses up any of my outfits and can instantly give you a completely different look. Stack rings and bracelets on the outside of your outerwear (over the top of coat sleeves or gloves), layer over your roll neck or add some chunky earrings to give a different dimension. Hiho’s rings are the perfect stacking companion (I always wear 3 rings on my middle finger including the fern and daisy rings from Hiho). The iconic cherry rollers are also a great equestrian inspired addition!

Sunglasses – rain or shine, sunglasses are always a statement!
Gloves – perfect for finishing off your look (and keeping your fingers warm!)

Belts – a statement belt is a huge way to change the look of your outerwear. I have often taken the matching belt from my coat and replaced it with something else. I also love the look of oversized blazers (and even puffa coats!) paired with a statement belt – go for thinner one with more refined tailoring and all out with a chunky belt if you’ve got a heavier coat.
Umbrella – There is no place in my world for frizzy, rain-soaked hair (at least not on a day out!), so having an umbrella stashed in my bag is a must!

Handbag – one of the biggest accessories and a huge way to influence your outfit. There’s so many to choose from and I personally think handbags (much like shoes) are very individual, so rather than recommending a particular bag, my advice would be to take the right sized bag. You need something big enough to fit your umbrella, your sunnies, the race tickets, phone, keys etc. etc. so make sure it’s big enough to carry everything comfortably. Speaking of comfort, don’t take a huge bag with you… you’ll have to carry it around all day and it can soon get too heavy! A bag with a cross strap is also a great idea. 
Being very petite, I love a heel. However, there is nothing worse for your refined and elegant look than hobbling around all day because your feet hurt! You will be stood up for a lot of the day, so make sure you wear something that is comfortable first and foremost. If you are going with a heel (as I will be doing!), make sure it's either low, or chunky (or both!), and you’ve tried out the shoes before you wear them! I would always recommend a boot rather than a shoe (comfort and practicality – it’s less painful if you get stood on in the crowd!). 
I hope this helps you choose an outfit for the races that makes you look and feel your best – if you’re there, do say hello if you see me around!


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