The British social season is back once again for 2026, and nothing gets us geared up for the festivities ahead quite like the Cheltenham Festival. Racegoers - from royals and racing fanatics to fashion lovers - have been showcasing their race day finery here since 1860, making it one of the most stylish fixtures in the calendar.
Today, British heritage style sits at the top of the fashion agenda, with racegoers leaning into timeless tweeds, luxurious outerwear and statement accessories - all perfectly suited to the unpredictable March weather. Think sharply tailored coats, felt fedoras, leather gloves and knee-high boots: practical pieces elevated with plenty of polish.
Country lifestyle brand Holland Cooper returns once again as the official ladies’ fashion partner and, for 2026, also makes its debut as the Official Luxury Fashion Partner of The Jockey Club - a fitting collaboration given the brand’s signature blend of countryside elegance and contemporary tailoring.
In 2024, festival bosses announced that Ladies Day - traditionally the day that encouraged women to dress to impress - would be reimagined as ‘Style Wednesday’. The shift reflects the evolving nature of the event, recognising that the festival has become a showcase for sartorial individuality.
From royals like Zara Tindall to celebrities like Georgia Toffolo and impeccably dressed racegoers, this year’s festival is already delivering an impeccable display of dressing.
We may not know much about placing a winning bet on the horses, but there’s one thing we’re confident wagering on: the style at this year’s races is set to be second to none. And if the early arrivals are anything to go by, the fashion stakes are already running high.
Best dressed guests at Cheltenham Festival 2026
© PA Images via Getty ImagesLydia Millen
Lydia oozed chic in a checkered jacket and matching skirt with a shirt and tie, all from Holland Cooper.
© BRADLEY CARRANCEJAHero Fiennes Tiffin
The Young Sherlock actor stepped out on Gold Cup day wearing a full Holland Cooper look.
© @georgiatoffoloGeorgia Toffolo
Toff eschewed her usual dramatic dress code for an elegant jeans-clad race day look.
© PA Images via Getty ImagesZara Tindall and Harriet Sperling
The royal ladies opted for opposing colourways for day four. Zara stunned in burgundy tones (shoutout to the on-trend finged bag), whilst Harriet oozed classic glamour in grey houndstooth and black accessories.
© PA Images via Getty ImagesGemma Collins
Gemma Collins wrapped up warm in a longline coat with fur-trimmed sleeves for day three. To protect her hair and elevate the look, she wore a silk scarf around her blonde tresses.
© PA Images via Getty ImagesJade Holland Cooper
The ever-so-stylish Jade Holland Cooper opted for a head-to-toe look from her namesake label, Holland Cooper, on day three of the iconic event.
© PA Images via Getty ImagesGeorgia Toffolo
For day three of the event, Georgia Toffolo put a fashionable twist on the dress code, styling a sleek skirt-skirt with tights, a fluffy scarf and a velvet headband.
© PA Images via Getty ImagesZara Tindall
A very chic Zara Tindall dressed to impress for day two of the iconic event. Dressing in a longline check coat, the stylish royal made a strong case for touches of berry tones, matching her blouse to her headpiece. To complete the look, she wore a pair of Fitzrovia Heeled Boots and the Loxley Mini Crossbody Bag from luxury British brand Fairfax & Favor.
© Sportsfile via Getty ImagesAoife McNamara
Racegoer Aoife McNamara put a high-fashion twist on her look for the day. Styling a dark brown woollen skirt and a matching puff sleeve jacket, accented with white stitching and pearl buttons, the stylish attendee nailed the Cheltenham dresscode.
© Sportsfile via Getty ImagesLisa Walsh
Lisa Walsh proved the power of styling white and burgundy together. Opting for a tailored white skirt and fitted jacket co-ord, the all-white look was the perfect base layer to add touches ofdeep red.
© Sportsfile via Getty ImagesKatie Young
Tones of deep brown were on the cards for Katie Young's day two ensemble. The stylish attendee opted for a sleek tartan coat, which she wore cinched at the waist with a gold hardware belt. To elevate things, she also added a touch of fur in the form of leather gloves and a matching sash.
© PA Images via Getty ImagesJade Holland Cooper
Kicking things off in style for day two of the event, Jade Holland Cooper opted for a sleek, chic check maxi skirt and matching jacket combo.
© PA Images via Getty ImagesJade Holland Cooper
On Day One this year, Jade wore Holland Cooper by Jade Holland Cooper, combining earthy green and red tones. The designer opted for a checkered jacket and peplum maxi skirt set, paired with a shirt and tie and burgundy boots.
© @georgiatoffoloGeorgia Toffolo
Honestly? We look forward to seeing style queen Georgia's outfits every single year. And she's absolutely nailed this year once again. On Day 1, she opted for a vibrant red two-piece suit from Chanel layered with an Intimissimi top. Calzedonia tights, Massimo Dutti block-heeled sandals, a Jonny Beardsall Millinery hat and her husband's late grandmother's bag completed her incredible look.
© James WhatlingZara Tindall
The former equestrian and daughter of Princess Anne looked effortlessly cool, combining various shades of blue and greens. We love the vibrant pop of colour from her blouse, which hailed from Really Wild clothing, and the deep green croc-print Aspinal of London handbag. She also wore a wool jacket and skirt from The Fold London, and Fairfax & Favor's Regina High Heeled Boots in Black Suede.
© Getty ImagesPeplum Detailing
A guest leaned into the revival of the peplum hem in a black and white checkered mini skirt paired with a fluffy black jacket, a matching boater, knee high boots and a quilted Chanel handbag.
