Trump Obsessed With Milwaukee Shoes

Florsheim shoes. Photo by Toxophilus, (CC BY-SA 4.0), via Wikimedia Commons

President Donald Trump just loves Florsheim shoes, the suburban Milwaukee-owned brand “that’s been pairing comfort and style for more than a century,” a story Wednesday by The Wall Street Journal reveals.

“Trump Is Obsessed With These $145 Shoes—and Won’t Let Anyone Leave Without a Pair,” the headline declares.

“All the boys have them,” said a female White House official. Another joked, “It’s hysterical because everybody’s afraid not to wear them.”

Trump loves the shoes so much that he keeps a stack of them in the office and likes to give them to all the guys. Those proud owners of Florsheim shoes now include Vice President J.D. Vance, secretary of state Marco Rubio, transportation secretary Sean Duffy, defense secretary Pete Hegseth, commerce secretary Howard Lutnick, Trump’s communications director Steven Cheung, deputy chief of staff James Blair and speechwriter Ross Worthington.

Fox News personality Sean Hannity and Sen. Lindsey Graham also now own the hottest and most exclusive MAGA status symbol, courtesy of the president, who is said to pay for the shoes himself.

“During a lunch meeting in January, Trump suddenly pivoted to his ‘incredible’ new shoes and gave Tucker Carlson a pair of brown wingtips. … Recipients have taken to wearing their Florsheims around Trump, some apparently begrudgingly. One Cabinet secretary has grumbled that he had to shelve his Louis Vuittons.”

Florsheim, owned by a Wisconsin company since 2002, has a long and interesting history. It was founded in 1892 in Chicago by Sigmund Florsheim, a German immigrant, and his son Milton. The company outfitted American soldiers in both world wars. President Harry Truman wore them. So did the moonwalking singer Michael Jackson.

Its Milwaukee connection began when Thomas Florsheim Sr. (grandson of the founder) left the firm and joined Milwaukee’s Weyenberg Shoe Mfg. Co. in 1964, bringing Florsheim expertise to the local manufacturer. Weyenberg became the Weyco Group in 1976 and the Glendale-based company bought out the Florsheim company after it went bankrupt in 2001. Today the company’s CEO is Thomas Florsheim Jr., a fifth-generation Florsheim.

You might think he would be excited about Trump’s discovery of the company’s shoes, but the CEO said he was unaware of the president’s latest obsession and had no comment about it.

That might be because the company is not a supporter of Trump, nor his tariffs. It has led nine other Wisconsin companies, including iconic state brands like Kohl’s and Milwaukee Tool, in a suit against the administration demanding refunds of the money paid in tariffs, which the U.S. Supreme Court has declared were unconstitutional.

“The idea behind the tariffs originally was pro-business, and it feels like somehow the pro-business part of this has gotten lost,” Tom Florsheim Jr. said in a story by Haley Kosik.

The company imports shoes that are now made overseas. “Florsheim said his company has spent millions on tariffs over the past year,” the story reported. “He said at one point they were having to pay a 145% tariff on shoes made in China.”

“You’re paying more for the tariff than you were for the shoes,” Florsheim complained.

So the company shifted manufacturing to India, only to face new tariffs there.

“From a business planning standpoint, it’s been almost impossible,” Florsheim said.

Weyco was the first of the 10 Wisconsin companies to sue, back in December. Their suit requested that the U.S. Court of International Trade “declare the president’s unprecedented power grab illegal.”

After the Supreme Court struck down the tariffs, Weyco led the way in suing the Trump administration, demanding an “immediate refund” with interest.

The Weyco Group also has a political action committee that funds campaigns and all its money went to Democratic groups and candidates in 2024, according to Open Secrets.

Its CEO also led a group of local business leaders who supported Democratic candidate Kamala Harris against Trump in 2024. The group “started meeting somewhat regularly after the Jan. 6, 2021, attack on the U.S. Capitol and continued attempts to delegitimize the results of the 2020 presidential election,” said Florsheim, a Democrat, in a story reported by Jessie Opoien.

“We definitely don’t agree on policy, but everyone in our group puts that aside because we see this election as being much, much more than policy,” Florsheim said. “It’s about … the principles of democracy and that link to how that impacts the economy.”

Has anyone told Trump the company that sells his favorite shoe is suing him? Or did everything it could to defeat him in 2024? Here’s hoping a reporter is present when the president gets the news.