Kevin: That’s a great photo of Ride ‘Em Barack, though you at least have to give him credit for looking really, really embarrassed. I expect people to start mistaking you for him on the street. In fact, presidential candidates in stupid hats go back a long way—not just the Duke, but who can forget Hillary the lifelong Yankee fan:

(this was when she ran for senate in 2000)

or Camo Cap Kerry:

… and old-timers will recall Estes Kefauver in 1956:

Al Smith used his trademark derby hat as a symbol of his 1928 campaign, and the image was familiar enough that when he endorsed Wendell Willkie in 1940, the Willkie folks revived it:

As this site explains, Smith was a Democrat, but he hated FDR most of all.)There’s one thing these people have in common: They were all presidential losers. Leave it to Calvin Coolidge to set the record for Worst Presidential Head Covering Ever with this so-lame-it’s-cool get-up: