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JUST IN: Donald Trump Unleashes a SCORCHING ROAST on Taylor Swift and Her Outfit to Stephen Colbert tonight!, Calling It “A Total Fashion Disaster,” “A National Emergency in Sequins,” and “The Worst Dress Since Humanity Invented Clothes.” Trump Mocked Her Boots, Her Stylist, Even the Color of Her Lipstick — But What STUNNED Swifties Was What He Claimed Taylor Secretly Sent Him.
In a chaotic and comedic moment during his appearance on The Late Show with Stephen Colbert tonight, former President Donald Trump delivered a blazing, over-the-top roast aimed squarely at Taylor Swift and the shimmering outfit she wore to a recent awards show.
Trump, who appeared unusually energized, tore into Swift’s look, calling it “a total fashion disaster,” “a national emergency in sequins,” and even “the worst dress since humanity invented clothes.”
He didn’t stop there. Trump poked fun at her boots, questioned whether her stylist was “a Democratic operative,” and jokingly suggested her lipstick color was “an attack on American values.”
Colbert, barely holding in laughter, repeatedly reminded the audience that the former president was “really committed to this fashion critique.”
But the moment that sent Swifties into full meltdown mode came near the end of the segment.
With a dramatic pause, Trump claimed—without explanation—that Taylor Swift once sent him a “very interesting letter” about her wardrobe years ago.
He hinted he “still has it,” wagging a finger as the crowd erupted. Neither Colbert nor the audience could tell whether he was joking, exaggerating, or teeing up a future punchline.
Swift’s team has not responded, but online reactions exploded instantly, with fans calling the interview everything from comedy gold to “the strangest crossover of 2025.”
For now, one question hangs in the air:
What exactly was in that so-called “interesting letter”… and does it even exist?
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