"She looks like the most beautiful actress ever to live. Actually, she looked very much like a great first lady, Melania. She didn't look like Kamala," he told the billionaire and Republican donor . "But of course, she's a beautiful woman, so we'll leave it at that, right?"
At a rally in Pennsylvania less than a week later, he said that he's far more attractive than his opponent. Though Trump's two-hour speech was supposed to focus on Harris' economic policy proposals , he came back to the question of her appearance and the Time cover, saying sarcastically that he thought the illustration might be of Sophia Loren or Elizabeth Taylor .
" Don't ever call a woman beautiful, because that'll be the end of your political career," he warned the cheering crowd. "But I say that I am much better looking. I'm a better-looking person than Kamala."
Later on in his remarks, Trump returned to the topic once more, apparently unable to help himself despite Republicans' pleas that he focus on policy, not personal attacks .
"They said, ''No, her biggest advantage is that she's a beautiful woman.' I'm going, huh? I never thought of that. I'm better looking than she is," he told the crowd.
There was the 1990s, when he quipped that "it doesn't matter what [the media] writes as long as you've got a young and beautiful piece of ass." In the early aughts, he bragged about seeing half-naked Miss Universe contestants and made his infamous "grab them by the pussy" comment.
While running for president for the first time in 2016 , Trump directed his jabs toward Republicans and Democrats alike. Talking about his primary opponent Carly Fiorina, Trump told a reporter, "Look at that face! Would anyone vote for that? Can you imagine that, the face of our next president?"
He branded Hillary Clinton a "nasty woman" and referenced her marital troubles, writing on Twitter in 2015, "If Hillary Clinton can't satisfy her husband what makes her think she can satisfy America?"
Though gender is inevitably on display in this year's election, Harris is not making it a cornerstone of her campaign as she gears up for the convention , putting her election bid in stark contrast to Clinton's. Despite the historic nature of her candidacy as the first Black woman and South Asian American person to headline a major party ticket, Harris is instead focusing more on her middle-class and prosecutorial background, Politico reported .
When Clinton ran, she leaned heavily into the prospect of becoming the first female president, even embracing the slogan, "I'm with her." Harris has been relatively uninterested in focusing on her identity throughout political campaigns and instead talked more about her record, the Washington Post reported .
Beyond that, though, Harris represents a broader change among female politicians focusing less explicitly on their gender since 2016. Though women running for office still face sexist headwinds, some argue that Clinton made the American electorate more comfortable with a female candidates and paved the way for Harris to focus on other issues.
The former Secretary of State "got us to a place where it's not front-and-center, and it's not the first thing voters look at," said Patti Solis Doyle, who managed Clinton's 2008 run.
Trump, for his part, still appears to be taking a page out of his 2016 playbook.
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