Trump Pits ‘Woke’ Taylor Swift Against Sydney Sweeney, Saying Pop Star Is for ‘Losers’ and Calling Sweeney’s Ad the ‘Hottest’

President Donald Trump is fueling a pop culture clash by casting Sydney Sweeney and Taylor Swift as symbolic opposites on the political and cultural spectrum.

During a conversation with reporters on Sunday, Aug. 3, Trump was informed that Sweeney is a registered Republican. He responded with enthusiastic praise for the actress and her headline-making American Eagle ad campaign, which has faced criticism over its perceived messaging.

The next morning, Trump doubled down in a Truth Social post, going as far as to compare his admiration for Sweeney with his disdain for Swift — who endorsed Democrat Kamala Harris in the 2024 election.

“Sydney Sweeney, a registered Republican, has the ‘HOTTEST’ ad out there. It’s for American Eagle, and the jeans are ‘flying off the shelves.’ Go get ‘em Sydney!” Trump wrote on Aug. 4.

He also took aim at other companies with so-called “woke” ads, including Bud Lite and Jaguar, before shifting his attention back to Swift, a frequent target of his in recent months.

“Just look at Woke singer Taylor Swift,” he added. “Ever since I alerted the world as to what she was by saying on TRUTH that I can’t stand her (HATE!). She was booed out of the Super Bowl and became, NO LONGER HOT.”

Trump concluded his post with a broader statement: “The tide has seriously turned — Being WOKE is for losers, being Republican is what you want to be. Thank you for your attention to this matter!”

The president’s public feud with Swift intensified after she publicly endorsed Harris in September 2024, prompting Trump to post: “I HATE TAYLOR SWIFT!”

Despite his rhetoric, not all of Trump’s family members share his hostility toward the pop star. His granddaughter Arabella, daughter of Ivanka Trump, remains a fan and celebrated her 13th birthday at Swift’s Eras Tour in October.

Sweeney’s political affiliation became public after BuzzFeed News reported she was registered Republican — a revelation that coincided with backlash to her recent American Eagle ad.

The campaign, titled “Sydney Sweeney Has Great Jeans,” plays on the word “genes.” Critics argued the campaign suggested a kind of genetic superiority, especially with its focus on her blonde hair and blue eyes.

It also drew comparisons to Brooke Shields’ infamous Calvin Klein ad from 1980, which caused a stir due to Shields’ young age and the suggestive tagline: “You want to know what comes between me and my Calvins? Nothing.” Like Sweeney’s ad, it was accused of promoting idealized traits being passed down generationally.

Sweeney has not commented publicly on her political beliefs or on Trump’s public praise.