What to wear at the Races

With the Cheltenham Festival less than a month away, you might well be looking ahead at the Flat racing season with an element of anticipation. After all, there is nothing quite like a day at the Races – it’s one of those occasions when heritage meets high fashion and so, who better to advise you on what to wear at the Races than the Official Luxury Fashion Partner of The Jockey Club, Holland Cooper. Here we’ve teamed up with the luxury British heritage clothing brand to offer you 10 suggestions to help you be among the best-dressed guests on the turf.

When you are designing for Holland Cooper, what is the ‘one golden rule’ you keep in mind to ensure an outfit is both practical for the elements and high-fashion?”  

“My golden rule is simple: practicality should never compromise style. I always design with real life in mind, layering is absolutely essential. Beautiful, purposeful layers, starting with a great roll neck, mean you’re prepared for every element while still looking effortlessly polished. Footwear is just as important, a chic flat boot is perfect for long race days, and I always love finishing with leather gloves, which are both practical and such a timeless accessory. It’s all about feeling comfortable, confident, and put together.”

Jade Holland Cooper

The foundation

Your racing attire needs to start with structure. With British weather being unpredictable at best, your outerwear needs thought. Have a look at these suggestions that will give you the confidence to step from the car to the parade ring in a way that’s effortless.

Tailored Peplum Jacket in Dark Green Herringbone

This tailored peplum jacket is a masterstroke of architectural femininity. Handcrafted in the UK from 100% Scottish wool, it comes in a dark green that is designed to feel grounded yet quietly commanding, perfect for both grandstands and country walks.

What are the subtle design details you include to elevate a tailored look into something that feels truly special for a high-profile social event? 

“It’s always in the details. I love combining sharp, structured tailoring with softer textures, considered hardware, and subtle feminine touches, those are the elements that truly elevate a look. Thoughtful styling can make all the difference too; our new silk scarf in collaboration with Boodles adds a beautiful pop of colour against tweed, bringing warmth and personality to classic tailoring. It’s understated, yet confident –  exactly how I want a woman to feel when she wears Holland Cooper.”

Jade Holland Cooper

Knightsbridge Blazer in Emerald Houndstooth

If the peplum is about form, the Knightsbridge is about presence. This wardrobe staple in Emerald Houndstooth is a vibrant, cinematic pop of colour against the Cotswold green, and finished with those signature gold Holland Cooper rivets.

The Single Breasted Blazer in Navy Duke

And let’s not forget that the gentleman need to look race-ready, too. This single-breasted blazer, elegantly lined with a luxurious satin twill, is far more sophisticated than a standard black blazer and perfect for transitioning from the paddock to a post-race dinner.

The Single Breasted Blazer in Mono Herringbone

Or how about the same blazer in mono herringbone? Meticulous, tidy and effortlessly commanding, and finished with traditional Holland Cooper detailing and braided lapels, it would suit the sharpness of the city just as well as it would a day at the races.

Traditional silhouettes

It’s one thing to look great standing still in front of a mirror, but a race day involves leaning over the rails, navigating through crowds, and being on the move from the paddock to the grandstand. You want pieces that have a bit of life to them, and with a fit that actually lets you enjoy the day without constantly havig to make adjustments.

360 Maxi Tweed Circle Skirt in Dark Green Herringbone

New for the season, and with a sense of effortless grandeur, this chic circle skirt will capture the wind as you walk. It draws its inspiration from the rolling hills and deep moss tones of the British countryside in late winter, and pairs perfectly with the peplum tailored jacket.

Race days are notoriously long and weather-dependent. What is your secret to transitioning from a chilly morning by the track to a more formal indoor lunch?  

“Race days are famously long, and entirely at the mercy of the weather. For me, it’s all about thoughtful layering, so you stay warm trackside while ensuring there’s something beautifully polished underneath once you head indoors. Elevated knitwear is always my go-to, effortlessly chic, endlessly versatile, and perfect for transitioning from crisp mornings to formal lunches. I’ve also been loving our new 360 Maxi Tweed Skirt. Crafted in our signature tweeds, it’s timelessly elegant, wonderfully warm, and designed to feel feminine and refined the moment you slip off your coat.It’s that balance of practicality and polish that makes all the difference.”

Jade Holland-Cooper

Knightsbridge Maxi Skirt in Emerald Houndstooth

This is for the woman who wants to elongate the frame. High-waisted and statuesque, it turns the walk from the car to the enclosure into a catwalk. It’s heritage tweed, but with the saturation turned all the way up.

Ariella Blouse in Oyster

Beneath the heavy wools, it can help to have a little softness. Designed with a fluid drape with a statement oversized bow collar, this blouse has been beautifully created from an elegant satin fabric. 

The finishing touches

The difference between a good day at the Races and a great one often comes down to the finer details. You don’t want your heels sinking into the grass the moment you leave the concrete, for example. Whether it’s the texture of a tie or a sturdy pair of boots that can actually handle the turf, it’s these details that will make you feel put-together rather than just “dressed up”.

Regency Mid-Heel Ankle Boot in Rich Chocolate

With its block-heeled stability that respects the turf, The Regency will allow you to avoid the ultimate race-day faux pas of “stiletto sink”. Available in three new premium leather colourways, the rich chocolate option provides a grounded luxury to tie your entire ensemble together.

How do you suggest using accessories to tie an outfit together without over-complicating the look?

“I always believe choosing one standout accessory. Effortless, refined, and never overdone. A silk scarf is a timeless finishing touch. It can introduce a subtle pop of colour or perfectly complement tweed, instantly elevating an outfit. And this Ladies Day at the Festival, we’re launching a beautiful co-branded silk scarf with Boodles – a truly special piece that brings together heritage craftsmanship and modern elegance. It’s those thoughtful details that really complete a look.”

Jade Holland Cooper

Men’s Chelsea Boot in Chocolate

The men’s Chelsea boot is built for a day spent on your feet. It’s understated, but robust and impeccably made. Fully lined in supple leather for all-day comfort, the design is finished with a resin rubber outsole for durability and grip on a variety of terrain. 

Jacquard Tie in Brown

For a final raceday flourish, how about a tie? This one features a signature all-over Holland Cooper monogram and a subtle sheen for elevated texture, it is designed to complement both formal and smart-casual styling.

Find Holland Cooper at The Orchard at this year’s Cheltenham Festival

A day at the races isn’t just about the results on the track; it’s also about how you feel.

When the racing is over, what is it about a Holland Cooper look that makes it stand out as the ‘gold standard’ of race-day style?

“For me, it’s all about timelessness. A Holland Cooper look is never trend-led – it’s rooted in heritage, craftsmanship, and thoughtful design. Race-day style should feel polished without being forced. It’s that balance of practicality and femininity. Ultimately, it’s about investing in clothing that transcends the day itself, looks you’ll return to season after season. That’s what makes it the gold standard.”

Jade Holland Cooper

And this year, in addition to watching performances on the track, you can find Holland Cooper at The Orchard, Cheltenham Festival’s exclusive, high-end shopping and experiential sanctuary. Go and say hello, find your fit, and make sure your race-day story is written in style. And maybe – just maybe – you’ll also get a glimpse of one of the impeccably-dressed Holland Cooper Racing Legends that include the likes of Richard Johnson OBE, one of the most prolific National Hunt Racing winners, or the legendary trainer and dual Champion National Hunt jockey, Jonjo O’Neill.

Disclosure: This post is sponsored by Holland Cooper. Follow on social media at @jadehollandcooper @hollandcooperclothing

Paul Johnson

Paul Johnson is Editor of A Luxury Travel Blog and has worked in the travel industry for more than 30 years. He is Winner of the Innovations in Travel ‘Best Travel Influencer’ Award from WIRED magazine. In addition to other awards, the blog has also been voted “one of the world’s best travel blogs” and “best for luxury” by The Telegraph.