The Last Cocked Hat

Even if you are the commander in chief, fashion may be a capricious mistress. James Monroe, the fifth President of the United States and the man who gained the nickname "the Last Cocked Hat," learnt that lesson. This nickname made fun of Monroe's antiquated fashion choices. He continued to dress in the American Revolutionary style, complete with knee-breeches, white, powdered wigs, and the tricorn hat, even though he was in government in the 1820s. Because the presidents who came after him wore more contemporary clothing, Monroe earned the nickname "the final cocked hat."

Although we don't know how Monroe felt about it, we can at least say that the moniker was still affectionate and was never meant to be used in a disparaging manner, which is obviously not the case for all the entries on this list. This nickname followed him about for the rest of his life. In relation to that...

• 5th President of the United States

In office: March 4, 1817 – March 4, 1825

Vice President: Daniel D. Tompkins
Preceded by: James Madison
Succeeded by: John Quincy Adams