From John F. Kennedy to the King of Pop, influential American men have been at the center of some of the most culture-defining shoe moments. Here, FN taps into some of the culture-defining American men’s shoes of the past 250 years. And don’t forget Florsheim, which had a high-profile moment earlier this year when Donald Trump was discovered to be gifting the brand’s footwear to agency heads, lawmakers and White House advisers. Inside a Red Wing shoe factory in 2026. And Danner, which started out making boots for loggers in the Pacific Northwest, jumped on the hiking boom in the 1970s.