But this stark political dissonance did not stop the British Prime Minister from choosing to wear a gigantic Frida Kahlo bracelet to her crucial Conservative Party conference speech on Wednesday.
Nevertheless, viewers were quick to point out the irony in Ms May endorsing the radical Mexican painter who had an affair with Soviet politician and Marxist revolutionary Leon Trotsky.
Critics on social media argued the artist, who used her work to explore questions of postcolonialism, gender, class, and race in Mexican society, would have spurned the British PM if she was alive.
Others quipped that Ms May’s drawn-out bout of coughing, which saw the world leader forced to apologise after losing her voice, was the result of her Kahlo bracelet.
“Theresa May wears a bracelet of Marxist political icon Frida Kahlo and she nearly chokes to death. Coincidence? I think nat,” joked Twitter user, Frankie Leach.
“Theresa May wearing Frida Kahlo bracelet - a disabled bisexual woman of colour and a Communist to boot. Sure they would have got along!” said another.
"Theresa-May-wearing-frida-bracelet is the smoothest distillation of the phenomenon that gave us 'Thatcher was a feminist icon' bulls***," said another.
“Why is Theresa May wearing a bracelet with Frida Kahlo, everyone's favourite Marxist artist, for her speech? Seems somewhat off-brand,” questioned one more.
Kahlo, who is the most popular and recognisable Mexican artist in the world, joined the Mexican Communist Party in 1927. There she met her husband and celebrated muralist Diego Rivera and was thrust headfirst into a tight-knit circle of activists and artists.
Kahlo, who is famed for her self-portraits, was known for decorating her corsets with hammer and sickles. She was even laid to rest under a Communist flag when she died.
In the wake of her death, she has become an icon for political movements and minority groups such as the LGBTQ community, feminism, and the Chicanos.
Ms May’s keynote address at the Tory conference was not devoid of other controversies and also found itself interrupted by a prankster who handed her a P45 form - a tax document given to employees when they are sacked or resign. A close-up photo of the fake P45 showed it listed the “reason for termination” as “neither strong nor stable”.
Greater Manchester Police confirmed that Simon Brodkin, a comedian who performs under the stage name Lee Nelson, was arrested for breach of the peace after the incident but released a short time later.
He was bundled into a security tent to protect him from the press before being cuffed and taken out of the Manchester conference centre. He made no comment to The Independent as security guards rushed him outside but earlier shouted: "Boris made me do it. He's left me in the lurch."
Around the same time he also tweeted: "Hi Boris Johnson, I gave Theresa her P45 just like you asked."
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