“Rough Rider” Hat - National Parks Gallery

In April, 1898, TR resigned his position as Assistant Secretary of the Navy to join the 1st Volunteer Cavalry. He wrote to a friend that “for the last year I have preached war with Spain. I should feel distinctly ashamed…if I now failed to practice what I have preached.” He went to war in uniforms made by Brooks Brothers and 11 extra pairs of eyeglasses.