Cheltenham Races

I’ve attended many race days over the years but 2025 was my first visit to Cheltenham Races for the Gold Cup.

What’s worth knowing straight away is that there’s no strict dress code at Cheltenham, and it isn’t a floaty-dress-and-heels kind of race day. It’s not Ascot – it’s Cheltenham in March. Forget that, and you really will end up with aching, wet feet… and be absolutely freezing!

Even if you’ve not got Cheltenham planned, this is exactly the kind of event that highlights something I see all the time – trying to get the balance right between looking good and dressing appropriately.

Because I know what suits me, I had a clear idea of the look I wanted. That made pulling my outfit together much easier.

But for a lot of people, events like this can feel stressful and trying to get that balance right.

Which is the key point – the difference wasn’t that I bought better clothes, it’s that I knew what worked for me.

What to expect at Cheltenham

Chances are, you’ll walk more than you think. The course itself is huge and a fair distance from the train station. Even the drop-off point still involves a walk to the concourse.

Then there’s moving between food areas, toilets, and finding the best spots – it’s a lot of standing, walking, and being outdoors for most of the day.

At the risk of sounding like I’m 100 years old, thermals are a wise investment. The wind that cuts across the course can be biting in March. Even on a dry, bright day, it can still feel cold, damp, and muddy underfoot.

It might not sound glamorous, but being prepared for that makes a huge difference to how much you actually enjoy the day.

Cheltenham is one of those events where what looks good on Instagram doesn’t always match the reality. And I saw that first-hand last year.

This year, I’ve already been asked for advice on what to wear, and it’s made me realise how much easier it is when you approach it with the right mindset. Because with a few simple tweaks, you can look good and be dressed for the day you’re actually going to have.

What actually works (based on experience)

– Your coat or outwear is just as important as your outfit. In many cases, it is the outfit!

– Footwear matters more than you think. If you’re not comfortable in heels, opt for flats or boots.

– Layers are non-negotiable. Thermal tops, tights and leggings will keep you warm all day.

– Accessories don’t just elevate your look – they keep you warmer too.

What I wore to Cheltenham in 2025

I was really pleased with my outfit last year, but more importantly, I felt comfortable and warm all day.

Here’s exactly what I wore:

– Thermal long sleeved top (under dress): Uniqlo
– Wool roll-neck midi length dress: Riess via Next Outlet
– Wool tights : over 10 years old!
– Knee length leather boots: Sergio Rossi
– Wool trench coat: Barbour
– Leather lined gloves: Ted Baker
– Faux-leather handbag: H&M
– Fedora Hat: Unbranded via Vinted

How to pull an outfit together

Putting together a Cheltenham-appropriate outfit doesn’t have to be complicated. I tend to focus on three things:

Colour – Stick to 2–3 colours to keep everything cohesive. I chose stone and beige tones and paired them with burgundy for a bit of depth.

Style – There’s definitely a “country” feel at Cheltenham, but that doesn’t mean you have to dress like someone else. It’s about adapting the look so it still feels like you. I kept mine simple with a classic tailored coat and a wool dress underneath. The hat isn’t something I’d usually wear, but it finished the look and made it feel more “Cheltenham”.

Fabric – Start with your base layers. Once your thermals are sorted, everything else becomes much easier to build. My thermal top and wool tights made all the difference.

I’m heading back again and already thinking about what to wear. I might re-wear the coat and hat and switch up what’s underneath. Or, I may go for something completely different.

If you’re planning on buying something specifically for the event, renting can be a great option — especially if you don’t see yourself wearing it again. Vinted is also worth a look if you’ve got something in mind on a lower budget. My hat was a great find last year and had never been worn.

Outfit inspiration

Pair a neutral like brown, beige, or navy with a pop of colour. Burgundy, green, or blue all work really well if you want something a bit more interesting.

Tailored coat + knit + skirt + boots
Smart coat + trousers + knit + ankle boots
Dress + tights + boots + structured coat
Cape + skirt + jumper + boots
Cape/coat + skinny jeans/leggings + long boots

Holland Cooper is a great source of Cheltenham inspiration and here’s a few others:

Putting outfits together that not only look good but actually work for real life is exactly what I focus on in my style and shape consultations.

If you’ve got an event coming up and find yourself overthinking what to wear, or buying things that don’t quite come together, that’s something I can help with.