Imelda May's tuxedo at Royal Ascot is a lesson in fashion rule-breaking

(L-R) Kate Silverton, Laura Whitmore, Emma Weymouth, Natalie Rushdie and Imelda May attend day 1 of Royal Ascot at Ascot Racecourse on June 18, 2019 in Ascot, England. (Photo by David M. Benett/Dave Benett/Getty Images for Ascot Racecourse)

Laura Whitmore and Imelda May attends day 1 of Royal Ascot at Ascot Racecourse on June 18, 2019 in Ascot, England. (Photo by David M. Benett/Dave Benett/Getty Images for Ascot Racecourse)

King Willem-Alexander of The Netherlands and Queen Maxima of The Netherland speak to Prince William, Duke of Cambridge and Catherine, Duchess of Cambridge on day one of Royal Ascot at Ascot Racecourse on June 18, 2019 in Ascot, England. (Photo by Chris Jackson/Getty Images)

Prince William, Duke of Cambridge and Catherine, Duchess of Cambridge on day one of Royal Ascot at Ascot Racecourse on June 18, 2019 in Ascot, England. (Photo by Chris Jackson/Getty Images)

Princess Beatrice and Princess Eugenie on day one of Royal Ascot at Ascot Racecourse on June 18, 2019 in Ascot, England. (Photo by Chris Jackson/Getty Images)

Prince William, Duke of Cambridge and Catherine, Duchess of Cambridge on day one of Royal Ascot at Ascot Racecourse on June 18, 2019 in Ascot, England. (Photo by Chris Jackson/Getty Images)

Prince Edward, Duke of Wessex and Sophie, Countess of Wessex pose for photographs ahead their 20th wedding anniversary on day one of Royal Ascot at Ascot Racecourse on June 18, 2019 in Ascot, England. (Photo by Chris Jackson/Getty Images)

thumbnail: (L-R) Kate Silverton, Laura Whitmore, Emma Weymouth, Natalie Rushdie and Imelda May attend day 1 of Royal Ascot at Ascot Racecourse on June 18, 2019 in Ascot, England. (Photo by David M. Benett/Dave Benett/Getty Images for Ascot Racecourse)
thumbnail: Laura Whitmore and Imelda May attends day 1 of Royal Ascot at Ascot Racecourse on June 18, 2019 in Ascot, England. (Photo by David M. Benett/Dave Benett/Getty Images for Ascot Racecourse)
thumbnail: King Willem-Alexander of The Netherlands and Queen Maxima of The Netherland speak to Prince William, Duke of Cambridge and Catherine, Duchess of Cambridge  on day one of Royal Ascot at Ascot Racecourse on June 18, 2019 in Ascot, England. (Photo by Chris Jackson/Getty Images)
thumbnail: Prince William, Duke of Cambridge and Catherine, Duchess of Cambridge  on day one of Royal Ascot at Ascot Racecourse on June 18, 2019 in Ascot, England. (Photo by Chris Jackson/Getty Images)
thumbnail: Princess Beatrice and Princess Eugenie on day one of Royal Ascot at Ascot Racecourse on June 18, 2019 in Ascot, England. (Photo by Chris Jackson/Getty Images)
thumbnail: Prince William, Duke of Cambridge and Catherine, Duchess of Cambridge  on day one of Royal Ascot at Ascot Racecourse on June 18, 2019 in Ascot, England. (Photo by Chris Jackson/Getty Images)
thumbnail: Prince Edward, Duke of Wessex and Sophie, Countess of Wessex pose for photographs ahead their 20th wedding anniversary on day one of Royal Ascot at Ascot Racecourse on June 18, 2019 in Ascot, England. (Photo by Chris Jackson/Getty Images)
Caitlin McBride

Imelda May has never been one for dress codes.

The Irish singer (44) has always marched to the beat of her own style drum, making for some of the most exciting red carpet additions at any event attends; but she outdid even her track record of style hits at Royal Ascot. May was among a group of exceptionally stylish women invited by a celebrity agency to enjoy the cosy surrounds of a VIP box at day one of the festivities, alongside Princess Diana's niece Lady Kitty Spencer and BBC journalist Kate Silverton.

Among the sea of bright reds, floaty prints, feathered sleeves and delicate headwear, Imelda stood all her own in a bespoke tuxedo by British designer Joshua Kane and a striking wide brim black hat by Victoria Grant, echoing Cara Delevingne's chic turn in a black suit and top hat as she attended Princess Eugenie's wedding last October.

The dress code at Royal Ascot is famously strict and organisers have no qualms about turning away guests who didn't fit the bill to a T.  There is a detailed style guide on the website which states that the dress code is "woven into the fabric of our history" and breaks down style requirements for particular enclosures, which become stricter they become more exclusive.

Laura Whitmore and Imelda May attends day 1 of Royal Ascot at Ascot Racecourse on June 18, 2019 in Ascot, England. (Photo by David M. Benett/Dave Benett/Getty Images for Ascot Racecourse)

Trouser suits have been welcome for some time, but they must be full length and the same material and colour, while jumpsuits are also welcome and a headpiece must be worn, but fascinators are forbidden in certain areas. Midriffs must be covered and strapless and off the shoulder cut tops are not allowed. while every hemline must be below the knee.

In response to the rising popularity of men wearing loafers without socks, they made socks a requirement for all male guests last year. And in 2012, dress code "assistants" were tasked with enforcing the rules by doling out pashminas and ties to those attending who may have missed the memo.

Since shedding her signature rockabilly image over the years, Imelda said she was inspired to adopt a more experimental approach to her personal style - first cutting her hair into a shaggy fringe, ditching the fit and flare vintage-style dresses and embracing a more tailored look so the focus could remain on her music.

"I think I just wanted everything to stop for a while. I always felt that, that felt like me, I wasn't pretending to be like that but then it became a thing. I almost felt like a caricature of myself for a while," she said in 2017.

"It became too much of a thing, you know? It wasn't feeling like me. I'm a songwriter, I was getting more known for how I looked and my hair."

Royal Ascot marked the beginning of five days of celebrations of one of the most exclusive racing events of the year and attracted royal guests from around the world including Britain's Queen Elizabeth, Prince William and Kate Middleton, Prince Andrew and Sophie of Wessex and King Willem-Alexander and Queen Máxima of the The Netherlands.