Queen Camilla, Princess Anne and Carole Middleton as they attend 'Ladies Day' at Cheltenham

For many it is the epitome of English country dressing. And with Cheltenham Ladies Day back on the social calendar for the first time in seven years, guests went the extra furlong.

When it came to the millinery, so wide were the brims and so tall the plumes that it made that other famous equestrian event, Royal Ascot, look rather tame.

But not every guest adhered to the same formula of headgear one-upmanship. 

One of the more sober hats of the day belonged to Carole Middleton, who wore a Hicks & Brown feather fedora costing a modest £115. 

But then, when your titfer has been worn by the Princess of Wales, perhaps that’s all the competitive advantage you need.

Catherine, who was not at Ladies Day, first wore it to church in Sandringham in 2020.

Where the princess teamed hers with a brown woollen coat, her mother opted for navy in a Prince of Wales check, accessorised with a brown faux-fur stole, brown suede boots and black leather gloves.

Carole Middleton was seen laughing and joking with Brendan Moran.

Queen Camilla, Princess Anne and Carole Middleton as they attend 'Ladies Day' at Cheltenham

Queen Camilla, Princess Anne and Carole Middleton as they attend ‘Ladies Day’ at Cheltenham 

Carole had a check-mate in Zara Tindall, who was dressed in a strikingly similar navy checked coat, £1,100, by Katherine Hooker

Carole had a check-mate in Zara Tindall, who was dressed in a strikingly similar navy checked coat, £1,100, by Katherine Hooker

Princess Catherine is pictured in the same fedora at Cheltenham in 2020

Princess Catherine is pictured in the same fedora at Cheltenham in 2020

Mr Moran is a consultant colorectal surgeon and honorary senior lecturer at the University of Southampton Cancer Sciences division.

The star of Ladies Day was surely Carole’s vintage black Hermes Birkin – similar bags currently retail on resale platforms for £50,000.

Carole had a check-mate in Zara Tindall, who was dressed in a strikingly similar navy checked coat, £1,100, by Katherine Hooker. 

She paired it with black leather culottes, a plum-coloured fascinator by Juliette Botterill, matching leather gloves and a £295 handbag and black boots – both by Fairfax & Favor.

Meanwhile, Queen Camilla chose a wide-brimmed brown Philip Treacy hat decorated with a bold cluster of feathers. 

She paired this with a collarless beige coat by her favourite designer, Anna Valentine, brown suede boots and a £695 bag by Aspinal of London.

Also looking dapper was Princess Anne, in a single-breasted bottle green coat, matching hat, black leather boots and black leather gloves. 

Racegoers dressed in tweed attend day two of the 2026 Cheltenham Festival

Racegoers dressed in tweed attend day two of the 2026 Cheltenham Festival

Carole Middleton was seen laughing and joking with Brendan Moran

Carole Middleton was seen laughing and joking with Brendan Moran

Entrepreneur Jade Holland Cooper wore her navy wide-brimmed hat with a cream and navy checked peplum jacket and maxi skirt from her own label

Entrepreneur Jade Holland Cooper wore her navy wide-brimmed hat with a cream and navy checked peplum jacket and maxi skirt from her own label

Whether she keeps an eye on the catwalk or whether the catwalk has simply caught up with her perennially classic sense of style is a matter of opinion, but the brooch on her collar certainly paid lip service to one of this season’s biggest trends.

If brooches are in fashion for spring, so too, are the Peaky Blinders. Windowpane checks, flat caps, waistcoats and tweeds were the order of the day, for men and women both.

Entrepreneur Jade Holland Cooper, founder of the clothing company Holland Cooper, wore her navy wide-brimmed hat with a cream and navy checked peplum jacket and maxi skirt from her own label.

After the last Cheltenham Ladies Day in 2019, some opined that the event was too outdated to continue. 

On Wednesday, the ladies proved this theory wrong. When it came to fashion at least, peaky or otherwise, they seemed determined to play a blinder.

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