Cheltenham Races November Meeting 2025: What to Wear & Full Style Guide

The Cheltenham Races November Meeting: What to Expect & What to Wear

There’s something truly special about Cheltenham in November. The Cotswold air is crisp, the countryside glows in golden hues, and the buzz of excitement builds as racing fans, fashion enthusiasts, and countryside lovers gather for the Cheltenham Races November Meeting — one of the most anticipated fixtures of the National Hunt season.

Seen as the curtain-raiser to the jump racing season, the November Meeting offers three days of exceptional sport. Whether you’re attending for the first time or returning as a regular, it’s the perfect opportunity to embrace timeless countryside fashion with a refined edge.

The Three Days of the Cheltenham November Meeting

What can you expect at the Cheltenham November meeting this year?

Day One: Countryside Day (Friday)

The opening day sets the tone – it’s a relaxed, authentic day. Expect country displays, alongside thrilling jump racing.

Style cue: Tweed, waxed jackets, and layered textures shine here. This of this day as countryside chic meets race day glamour.

Day Two: Super Saturday

Saturday is always the highlight of the weekend. The grandstands buzz with energy, the racing is electric, and fashion is at its finest.

Style cue: This is the day for bold tailoring, statement hats, and luxurious accessories. Think refined, feminine, and confident.

Day Three: Carnival Sunday

Sunday slows the pace slightly, perfect for families and those wanting a more relaxed race day.

Style cue: By day three, think cosy knits under a smart jacket, comfortable boots, and subtle accessories – chic, warm, and perfectly practical.

The Ultimate Cheltenham Races November Meeting Style Guide

The Cheltenham November Meeting offers a fabulous opportunity to dress to impress! With rich fabrics, layered textures, and the right accessories, you’ll look every bit the part – confident, elegant, and effortlessly country classic.

When planning your Cheltenham Races outfit, the key is to balance warmth, practicality, and timeless elegance. The weather can change in moments, so layering and thinning about your fabrics are essential.

Let’s break things down, and start from the top!

1. The Hat – Your Race Day Essential

Depending on the race meet, I would either opt for a fedora or fascinator at the races. The November meeting is generally that little bit ‘dressier’, therefore if you want to style a fascinator you absolutely can!

A fedora or wide-brim hat is another great option. It will complement the country classic of your outfit, and handles the weather beautifully, come rain or shine!

When it comes to fascinators, you really can go with whatever! I love the bigger the better, but equally understated looks offer refined elegance. For a fedora, opt for rich tones – olive, chestnut, or navy. Add a feather pin or ribbon band for a personal touch.

2. Outerwear – The Heart of Your Outfit

When it comes to National Hunt Racing, your coat will do most of the talking – given this racing is over the winter months. Think warm and practical, but tailored and stylish.

Tweed or wool coats or trenches are the iconic racing look. But capes can look equally fabulous and have a slight edge which can look tremendously chic.

3. The Mid-Layer – Structure & Sophistication

Add depth with warm, elegant layers. Might sound old of me, but a vest is best! Use thinner layers to trap warm air and prevent that Cheltenham chill from getting to you.

Roll neck jumpers work really well as you can layer underneath, without bulk.

4. The Bottom Half – Sleek & Streamlined

A wool/tweed skirt with opaque tights for a feminine twist is a classic look, whilst trousers offer good warmth for cooler days. If opting for trousers, I would avoid blue denim for a more elevated look, think chocolate, stone or olive trousers.

5. The Boots – Where Elegance Meets Practicality

The ground can be soft, and the weather can be wet, so choose boots that handle weather stylishly. The November meeting is really high heels weather. Think suede or leather boots – you’ll see a lot of Fairfax & Favor.

Don’t forget to waterproof your suede boots if the weather looks wet! I use Liquiproof.

6. The Accessories – Finishing Touches

Accessories are the ultimate way to bring your final look together. Think the rule of three if you don’t know where to start. Three pieces in the same colour, split across thirds of the body. For example a hat/fascinator, belt and bag. This helps to create a really well put together outfit. Equally if you have tan boots, maybe think about a tan belt or bag and a tan hat. It helps to keep your outfit in proportion.

Shop my Guide:

Outfit One – The Tweed Suit – Effortless Country Style

Full Outfit: Holland Cooper Clothing. Hat: Hicks & Brown.
Shop the look: Outfit One

Outfit Two – Black & Red – Classy & Sophisticated

Jacket: Welligogs. Hat: Josephines Country Collection. Jumper/Jeans: Holland Cooper Clothing. Boots/Bag/Belt: Fairfax & Favor
Shop the look: Outfit Two

Outfit Three – Pretty in Plum – Seasonal Style

Hat: Josephines Country Collection. Jacket/Boots/Bag: Fairfax & Favor. Jumper: Marks & Spencer. Skirt: Joules.
Shop the look: Outfit Three

So there we have it my Darlings, you’re all set for Cheltenham!

See you there!

Lots of love, Lucinda xo

“Get ready for the roar!”
– Unknown

Discount codes:

Salthouse England – ‘LUCINDA10’ (10% off) (www.salthouse.co.uk)
Welligogs – ‘LUCINDA10’ (10% off) (www.welligogs.com)
Fig & Twig – ‘LUCINDA10’ (10% off) (www.figtwig.co.uk)
Spanish Boot Company – ‘countryclassiclucinda’ (10% off) (www.thespanishbootcompany.co.uk)
Katie Loxton – ‘KLDTI5O8’ (15% off) (www.katieloxton.com)
Lovall – ‘LOVALLLUCINDA10’ (10% off) (www.lovall.com)

*Affiliate – codes work online on most full priced items, direct from brand websites.
All codes active, and in working order, at the time of publishing.

Shop my looks on LTK:
Country Classic Lucinda LTK