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Get The Cheltenham Festival Look | Ladies Style Guide
Cheltenham races are part of the area’s history, with records dating back 200 years. The first Cheltenham festival as we know it was held in 1911, and it has transformed and adapted over the years to become the four-day event of today.
For many country sports lovers, Cheltenham Festival is the main event of the year. Hundreds of thousands of people flock to the Gloucestershire town across the four days of activities, hoping to either back the right horse or impress with a carefully selected range of outfits.
While there is no official dress code at Cheltenham, in an effort to improve accessibility and inclusivity, there are key fashion pieces that are at the forefront year after year. Some brands were almost born to be worn at Cheltenham, such as Dubarry with its amazing collection of tweed. We’re also proud stockists of Holland Cooper – the official Luxury Fashion Partner for the festival. Read on for our selection of the best brands and products to create that iconic Cheltenham look.
TIMELESS TWEED
Tweed is a Cheltenham staple. It provides that classic country style while also presenting a smart appearance, combining flattering tailoring and a range of natural tones. Pair a sophisticated tweed jacket with simple jeans or a tweed skirt for a complete matching outfit.
1. Holland Cooper Single Breasted Field Blazer
Holland Cooper hasn’t been chosen as Cheltenham’s Luxury Fashion Partner for any old reason – this tweed blazer is a truly premium piece, with a matching price tag. However, if you intend to splash out for the festival, this striking and sophisticated blazer is the one to go for. It’s comfortable, luxurious, and head-turning.
2. Holland Cooper Highgrove Coat
The stunning Holland Cooper Highgrove Coat is available in three beautiful classic colours; Glen Green, Chocolate Herringbone, and Charlton Tweed, new to Outdoor and Country for 2025. The tailored silhouette is incredibly slimming and flattering, with a mid-length, structured shoulders, and gold Holland Cooper hardware giving it the perfect race day aesthetic. You’ll also find a satin lining and suede to the underside of the collar for luxurious finishing touches.
3. Dubarry Hazelwood Tweed Poncho
If fitted jackets aren’t your style, Dubarry’s tweed poncho provides a twist on the classic Cheltenham outfit. Flowing and flattering, this woollen poncho still ensures warmth while also creating a more relaxed fit. The poncho fastens at one side, resulting in an elegant draping effect that adds a cosy and comforting layer to the design of this traditional and timeless Cheltenham statement piece.
4. Schöffel Moray Tweed Jacket
Schöffel is synonymous with country clothing, with the Ptarmigan Tweed Coat being one of their core pieces. For an alternative tweed piece that is much dressier than the brand’s staple shooting coat, the Moray Jacket is elegant, versatile, and perfect for a day at the races. Pair with the Schöffel Beauly Tweed Skirt for a complete country look.
Dubarry’s coats and jackets selection features some of the most iconic tweed pieces, such as these Outdoor and Country favourites:
HEAD-TURNING HATS
Headwear is often used as a statement piece, and that’s no different for Cheltenham outfits. From fancy feather fedora hats to old-school baker boy caps, there really is an option for any ensemble. Hicks & Brown take the lead in this category, with their extensive selection of colours, styles and decorative bands.
1. Hicks & Brown The Suffolk Fedora – Bronze Side Feather
Exquisite and elegant, this is just one of many high quality designs from Hicks & Brown. These hats are water resistant and comfortable, making them the perfect partner for all day wearing. You can also be sure that your hat is one of a kind, as all feathers used are unique by nature.
2. Holland Cooper Trilby Hat
Another premium offering from Holland Cooper, their trilby hat is available in multiple colours with complementary decoration. A leather inner trim and 100% wool felt construction combine for ultimate comfort.
3. Alan Paine Richmond Felt Hat
Statement pieces don’t have to break the bank. Alan Paine’s soft wool felt hat is decorative and stylish, and is available in a range of bold colourways designed to pair perfectly with any country inspired outfit.
4. Schöffel Newsboy Cap
For an all-out country look, pair your Cheltenham tweed with this soft and durable lambswool cap. Perfect for any weather, the cap is completed with contrast satin lining for a subtle hit of luxury. Why not bring something different to Ladies Day?
FLAWLESS FOOTWEAR
Unless you’re fortunate enough to be in a private box or the hospitality area, Cheltenham can involve a lot of standing around. Being on your feet all day means your primary concern when it comes to footwear should be comfort. Of course, this doesn’t mean that you have to sacrifice style! Here are some of our favourite festival footwear picks:
1. Ariat Tilbury Suede Boots
Nothing says country quite like a cowboy boot! This Cuban heeled boot crafted from suede with an Italian calfskin lining will look after your feet all day long. The moderate heel reduces calf ache, and the ankle height prevents any friction on your legs. Plus, a contoured cushioning insole ensures premium underfoot comfort.
2. Dubarry Downpatrick Boots
Dubarry are another brand known for their comfortable and reliable footwear. The Downpatrick Boots are a more streamlined and sophisticated model than their hard-wearing country designs like the Galway Boots, making them perfect for Cheltenham Races!
3. Penelope Chilvers Inclement Waterproof Tassel Boots
Penelope Chilvers knee length tassel boots are the perfect match for country inspired outfits. Inner cork and foam sole construction provide superior underfoot comfort, allowing you to stride around the racecourse in style without tiring.
Fairfax & Favor are renowned in the equestrian and country circles for their iconic boots. Often seen on the feet of riding teams and royals, Fairfax footwear is elegant, high quality, and long lasting. The iconic Regina boots are perfect for race day; they’re available in a wide range of colours and fits, with flat soles or heels depending on your preference. Don’t forget you can also personalise every pair of Fairfax boots with their ever expanding range of coloured boot and handbag tassels!
CHELTENHAM FESTIVAL ACCESSORIES
You’ve selected your tweed, chosen your comfortable footwear and topped everything off with an eye-catching hat. Now for the finishing touches!
A good handbag is truly an essential accessory for an event such as Cheltenham Races. It can keep your belongings safe and organised, and can also really be the element that ties an outfit together. Cross body bags are particularly useful as they reduce shoulder strain and improve security, while also keeping your hands free for the occasional glass of fizz! Here are some of our favourite bags:
1. Fairfax & Favor Finsbury Cross Body Bag
This staple from Fairfax exudes style and elegance. The main zipped compartment provides ample storage for essentials, and the design highlights the iconic Fairfax & Favor branding, with gold detailing, a removeable tassel and a long gold chain strap. You can also now opt for the Mini Finsbury for an even more streamlined look, with all the same familiar detailing.
2. Holland Cooper Soho Camera Bag
This soft suede camera bag from Holland Cooper is another versatile option for Cheltenham. Sure to complement any outfit, you can use the long elegant chain to wear it over your shoulder for a relaxed look and easy carrying. Subtle branding ensures a classy aesthetic that is ideal for pairing with some beautifully tailored tweed.
3. Dubarry Clara Saddle Bag
Available in four earthy colourways, the Clara Saddle Bag features an adjustable cross body strap and a secure main compartment. The combination of smooth and crushed leather creates a classic countryside look, making this bag the perfect finishing touch to your race day wardrobe. Plus, with the quality Dubarry is famous for, you know this bag will last for seasons to come.
Next, why not add a luxurious, flowing silk scarf to your outfit? With so many options for how to tie and wear these accessories, they’re the perfect way to change up your look throughout the event.
AND FINALLY…
Once your outfit is decided, make sure you relax and enjoy the atmosphere of Cheltenham festival! We can’t wait to see photos from the event – don’t forget to tag us @outdoorandcountry on Instagram, and use #outdoorandcountry on all your glamorous images!
