On The Nation Podcast: Derek Guy on how Trumpism swallowed Republican style.
Secretary of Homeland Security Kristi Noem and Attorney General Pam Bondi look on as US President Donald Trump speaks in the Oval Office on September 15, 2025.(Saul Loeb / AFP via Getty Images)
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Donald Trump and his MAGA movement haven’t just taken over Republican politics. They’ve also taken over Republican fashion.
Gone is the stuffy, genteel uniform of the elite. In its place: a loud, anti-establishment, even vulgar sartorial agenda. But what does this style actually say about MAGA politics? What do these clothes suggest about the authenticity of the movement’s leaders—especially when so many of Trump’s policies remain old-school conservative? And what messages do these looks send when their words often mean something else entirely?
To help us unpack the fashion evolution of the political establishment, we’re joined by Derek Guy—better known online as the Menswear Guy and creator of the blog Die Workwear!
Derek has written for The New York Times, the Financial Times, and other outlets. His essay, “From Blazers to Belligerence,” appears in the October books issue of The Nation.
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Donald Trump and his MAGA movement haven’t just taken over Republican politics. They’ve also taken over Republican fashion.
Gone is the stuffy, genteel uniform of the elite. In its place: a loud, anti-establishment, even vulgar sartorial agenda. But what does this style actually say about MAGA politics? What do these clothes suggest about the authenticity of the movement’s leaders—especially when so many of Trump’s policies remain old-school conservative? And what messages do these looks send when their words often mean something else entirely?
To help us unpack the fashion evolution of the political establishment, we’re joined by Derek Guy—better known online as the Menswear Guy and creator of the blog Die Workwear!
Derek has written for The New York Times, the Financial Times, and other outlets. His essay “From Blazers to Belligerence” appears in the October Fall Books issue of The Nation.
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Here's where to find podcasts from The Nation. Political talk without the boring parts, featuring the writers, activists and artists who shape the news, from a progressive perspective.
It’s no surprise that liberal philanthropy — a longtime pillar of the Democratic establishment — has become one of the Trump administration’s latest targets. As David Callahan writes in our December issue, liberal foundations “have often been depicted as the great puppet masters of the left, bankrolling and directing a who’s who of progressive groups intent on destroying the American way of life.” In other words, catnip for MAGA madness.
But as Callahan points out, the reality of how these institutions operate is far from radical. As powerbrokers of the elite, liberal philanthropists are averse to challenging “the systems that spawned them.”
How have liberal foundations failed to mobilize working-class Americans? And how can they ramp up the fight to defend the democracy they claim to care so much about saving?
Joining us to discuss this is David Callahan, founder and editor of Inside Philanthropy, and author of The Givers: Wealth, Power and Philanthropy in a New Gilded Age.
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D.D. GuttenplanTwitterD.D. Guttenplan is a special correspondent for The Nation and the host of The Nation Podcast. He served as editor of the magazine from 2019 to 2025 and, prior to that, as an editor at large and London correspondent. His books include American Radical: The Life and Times of I.F. Stone, The Nation: A Biography, and The Next Republic: The Rise of a New Radical Majority.
Derek Guyis a menswear writer who has written for The Washington Post, Esquire, and Business of Fashion. He’s also the author behind the men’s style site Die, Workwear!