Sneakerheads go crazy for Nikes. Donald Trump has a similar enthusiasm for Florsheim leather oxfords. But the shoemaker isn’t quite as fond of Trump and his policies.
Trump’s fondness for the shoes became well-known earlier this year, when it was reported he would buy pairs for his inner circle, after guessing their shoe size (not always accurately, as demonstrated by Secretary of State Marco Rubio).
That’s free PR for the brand, but the great-great-grandson of the company’s founder, who also happens to be the CEO of Florsheim’s parent company, is an outspoken opponent of Trump’s signature economic policy: Tariffs.
“The tariffs have changed fifteen times,” Thomas Florsheim Jr. told The Bulwark. “I think that many businesses felt that the Trump administration was going to be pro-business. And, you know, with the tariff situation, somehow the pro-business thing got lost.”
Made in America?
Florsheim is one of several footwear brands owned by Weyco Group. (Others include Nunn Bush and Stacy Adams). The company employs 350 people in the U.S., but as for the shoes? They’re made overseas, which is why tariffs have been such a headache for the company.
Shoemaking is labor-intensive, and manufacturing Florsheims in the U.S. would more than double their price.
“You really can’t make shoes and sell them in the U.S. unless you want to sell shoes for more than $300,” Florsheim said.
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Suing Trump
Last year, the company paid roughly $21 million in import duties and then was surprised with an additional bill for $1 million more. That’s when Florsheim had enough and sued the Trump Administration.
Weyco was one of the companies involved in the lawsuit that was ultimately successful and brought about $35.5 billion in refunds to companies who requested them. To date, Florsheim has recovered just $1.5 million of what it paid in tariffs.
It is, admittedly, an unusual strategy for a company to take legal action against its highest profile proponent. But Weyco has been unwavering in its criticism of tariffs, discussing them frequently on its most recent earnings call.
“Throughout 2025, new tariffs increased the cost of our products by 19% to 50%, resulting in gross margin compression despite a 10% price increase that took effect in July,” Florsheim said on the call. “With the IEEPA tariffs ruled unlawful and the administration implementing new tariffs, we are expecting continued cost uncertainty in 2026.”
That sort of talk is unlikely to quell Trump’s enthusiasm for the brand. He reportedly has kept a stack of them in an office to distribute to allies. And he pays attention to the footwear of his Cabinet.
JD Vance once told the story of Trump looking over the Resolute Desk and telling him and Rubio “Marco, JD, you guys have s—y shoes.” He then asked for their shoe sizes. “The president kind of leans back in his chair and says, ‘You know you can tell a lot about a man by his shoe size,’ ” Vance said.
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Chris Morris is a veteran journalist with more than 35 years of experience at many of the internet's biggest news outlets. In addition to his activities as a writer, reporter and editor, Chris is also a frequent panel moderator and speaker at major conferences, including CES and South by Southwest.
