The Cheltenham Festival: Where fashion, luxury and travel converge

Every March, as the UK starts to enjoy more Spring-like weather, a special kind of magic begins to stir in the heart of the Cotswolds – The Cheltenham Festival. Steeped in history and synonymous with prestige, this isn’t just a sporting event but a grand spectacle – a theatre of tradition where the thunder of hooves meets the rustle of heritage tweed, and where the finest racehorses in the world share the stage with the sartorially elite. Here, fashion is not an afterthought – it is part of the performance – and Holland Cooper takes centre stage as the racecourse’s official fashion partner.

For those who seek more than just another race meeting, the Cheltenham Festival is an immersion into British luxury. Here are just some items from the Holland Cooper range that will ensure that you remain as timeless as the event itself.

Constructed from the finest leather, the Cheltenham Bag blends vintage charm with contemporary finesse. Its structured top-handle design, complemented by a detachable cross-body strap, offers versatility without compromising on style. With a spacious interior and a secure zip pocket, it ensures that your race-day essentials are always within reach. Finished with Holland Cooper’s signature gold hardware and an elegant clasp, this bag transitions effortlessly from the grandstand to the winner’s enclosure. £329.

A delicate yet powerful statement of luxury, the Twilly in Nine Horse print is a nod to British craftsmanship. Made from pure silk and digitally printed in the UK, this versatile accessory adds a touch of equestrian elegance. Whether knotted around your neck, woven through your hair, or tied to your Cheltenham Bag, it elevates any outfit with effortless sophistication. Presented in Holland Cooper’s signature green box, it’s a perfect keepsake from the season’s most prestigious event. £79.

Petite yet striking, the Soho Mini Quilted Camera Bag is an embodiment of understated luxury. Featuring Holland Cooper’s signature dual-sided design—sleek quilting on one side and distinguished HC rivets on the other—this piece is a masterclass in craftsmanship. The leather-wrapped chain strap adds a polished finish, making it the ideal companion for the stylish racegoer, whether capturing memories on the course or enjoying a post-race celebration. £199.

This Holland Cooper coat commands attention, redefining classic tailoring with a modern silhouette. Handmade in the UK, it features a structured double-breasted front, belted waist and statement lapels. Military-inspired epaulettes add a hint of heritage, while the longline cut creates an air of effortless grandeur. Whether cinched in for a sculpted look or worn open for fluid movement, this trench coat is the ultimate outerwear choice for Cheltenham’s ever-changing weather. £849.

The Chiltern Cape is a masterstroke of heritage and high fashion. Designed with a relaxed silhouette and draping gracefully at the back, it offers a feminine yet powerful aesthetic. Trimmed with double-finished Toscana lambswool and accented with suede on the oversized sleeves, it embodies luxury. Finished with a signature back buckle, this Holland Cooper piece is a timeless companion for race-day elegance, perfect for layering over a roll-neck and tailored trousers for an effortlessly chic look. £679.

Holland Cooper‘s romantic reimagining of the classic white shirt brings together softness and sophistication. Crafted from the finest cotton and adorned with delicate lace trims on the collar and cuffs, it brings a touch of femininity to the structured tailoring that’s become synonymous with race-day style. Whether tucked into high-waisted trousers or layered beneath a tailored blazer, this shirt offers the perfect foundation for a polished Cheltenham ensemble. £149.

Stride through the festival with confidence in the Kensington Knee Boot—a perfect fusion of style and practicality. With a sleek pull-on design and a sturdy, chunky heel, these boots are built for both comfort and elegance. Featuring Holland Cooper’s signature branding and a classic racing green lacquered sole, they offer the perfect balance of equestrian heritage and contemporary fashion. Designed for a snug fit with an internal elastic gusset, they are an essential addition to your race-day wardrobe. £349.

A quintessential accessory for the Cheltenham Festival, Holland Cooper‘s Baker Boy Tweed Cap channels timeless country style. Handcrafted in the UK using the finest British-made wools, this cap offers a generous bucket fit and a curved peak for a sharp, polished look. Fully lined with satin for comfort, it pairs effortlessly with tailored pieces or casual knits, ensuring you stay warm and effortlessly stylish, come rain or shine. £79.

A refined finishing touch to any race-day look, the HC Classic Logo Belt is a testament to craftsmanship and detail. Made from soft, supple leather and featuring Holland Cooper’s signature gold logo loop and buckle, it adds a subtle statement to tailored trousers, dresses, or structured coats. Hand-finished with traditional techniques, this belt will finish your outfit with a bold yet stylish statement. £149.

Sleek, structured, and supremely stylish, the High Waisted Straight Trouser in Emerald Houndstooth exemplifies British tailoring at its finest. Cut from a luxurious wool blend and fully lined for comfort, these trousers offer a flattering high waist and a wide waistband that complements all body shapes. With deep side pockets and Holland Cooper’s signature gold hardware, they are the epitome of sophisticated race-day dressing, transitioning effortlessly from the course to an evening celebration. £299.

Disclosure: This post is sponsored by Holland Cooper.

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.