President Donald Trump’s latest White House obsession has taken an awkward turn. The 79-year-old commander-in-chief has been forcing top officials to wear $145 Florsheim Oxford shoes—and the company’s parent corporation is suing his administration over tariffs.
Vice President JD Vance, Secretary of State Marco Rubio, Defense Secretary Pete Hegseth, Transportation Secretary Sean Duffy, and Commerce Secretary Howard Lutnick are among dozens of officials who have received the leather dress shoes as gifts from Trump, who reportedly asks recipients at cabinet meetings: “Did you get the shoes?” White House aides say officials are terrified to refuse the footwear or fail to wear it around the president.
“It’s hysterical because everybody’s afraid not to wear them,” one White House official told reporters this week.
The bizarre ritual began late last year when Trump went searching for more comfortable footwear for long workdays. After settling on Florsheim’s cap-toe Oxfords, he started ordering pairs for others. The Chicago-based brand, founded in 1892, once supplied U.S. troops during both World Wars and was famously worn by Michael Jackson during his Thriller and Bad eras.
During one December Oval Office meeting, Trump reportedly peered over the Resolute Desk at Vance and Rubio’s feet and declared: “Marco, JD, you guys have sh**ty shoes.” He then pulled out a catalog, collected their sizes—11.5 for Rubio, 13 for Vance—and leaned back in his chair to announce that you can tell a lot about a man by his shoe size.
Trump has since developed what aides describe as a parlor trick of guessing people’s shoe sizes. Once satisfied, he instructs staff to place an order. A week later, a brown box arrives at the White House, sometimes bearing the president’s signature or a brief note. A small stack of labeled shoe boxes now sits in a nearby office, each tagged with a recipient’s name.
The president has gifted the shoes to communications director Steven Cheung, deputy chief of staff James Blair, speechwriter Ross Worthington, Fox News host Sean Hannity, Tucker Carlson, and Senator Lindsey Graham. During a January lunch meeting, Trump handed Carlson a pair of brown wingtips without warning. One cabinet member complained privately about having to retire his Louis Vuitton shoes. Some officials have even tried on the Florsheims in the Oval Office.
But Trump’s shoe evangelism has created an embarrassing problem: Weyco Group, Florsheim’s Wisconsin-based parent company, filed a lawsuit against the federal government on December 1, 2025, in the U.S. Court of International Trade over the president’s tariff policies. The complaint alleged Trump claimed authority to “unilaterally levy tariffs on goods imported from any and every country in the world” and sought a $16 million refund with interest for duties the company paid.
On February 20, 2026, the Supreme Court handed Weyco a significant victory, ruling 6-3 that the International Emergency Economic Powers Act does not authorize the president to impose tariffs. Chief Justice John Roberts wrote that IEEPA “contains no reference to tariffs or duties” and that “until now no President has read IEEPA to confer such power.”
CEO Thomas Florsheim Jr. told Spectrum News that his company paid tariff rates as high as 145 percent on shoes imported from China during 2025. Weyco moved production to India to avoid the China tariffs, only to face new duties there as well. The company raised prices by about 10 percent last summer and rushed approximately one million pairs of shoes into the U.S. ahead of tariff hikes—yet still absorbed millions in costs.
The irony cuts deep. While Trump personally pays for the shoes he distributes to allies, the very company making them bled millions because of his trade policies. After the Supreme Court ruling, Florsheim co-authored a piece praising the decision as “a decisive victory for the rule of law.”
When reached by phone, Thomas Florsheim Jr. said he was unaware of the president’s shoe orders and politely declined to comment further.
The 134-year-old brand has become an unexpected status symbol in Trump’s White House, where cabinet meetings can abruptly pivot to discussions about footwear. Officials say the president keeps a close eye on whether recipients actually wear their gifts. Photos of Rubio on January 7 show him wearing what appear to be Florsheims that look several sizes too large—with a visible gap at the heel—suggesting he may have fibbed about his shoe size to avoid Trump’s judgment.
The awkward situation exposes a broader tension in Trump’s trade agenda. Florsheim previously told reporters that while tariffs were supposed to be pro-business, “it feels like somehow the pro-business part of this has gotten lost.” The company characterized business planning under the constantly shifting tariff policies as “almost impossible.”
Meanwhile, Trump responded to the Supreme Court defeat by announcing new 10 percent tariffs under a different statutory authority. And he continues distributing the Florsheim shoes with the zeal of a traveling salesman, apparently unconcerned that the company keeping his feet comfortable just won a major legal battle against his administration.
