As the mayoral race heats up in Chicago, we thought it would be fun to look back on the history of the office. From top to bottom, Chicago’s mayors have a long-standing tradition of colorful antics, bottomless corruption and hat wearing. Perhaps our most notorious mayor was William “Big Bill” Thompson. He was mayor twice, on nonconsecutive occasions. His most famous tenure was between 1927 and 1931.

Former Chicago Mayor William "Big Bill" Thompson is seen here in this undated photo. He could frequently be seen wearing a bowler and was notorious for his corruptability and subserviance to mob boss Al Capone.

Winning the full support of Al Capone, Thompson hypocritically campaigned as a reformer to clean up the mob run city. Once in office, Thomson all but promoted Capone’s Southside mafia organization, turning a blind eye to everything from Capone’s breweries and stills to his executions of rival gang members in such events as 1929’s St. Valentine’s Day massacre. Openly in Capone’s pocket at the time, he did little without Capone’s consent. The press began dubbing Capone as the true mayor of Chicago.

Always the dapper dresser, Mayor Thompson was frequently seen dressed to the nines, topped by an elegant bowler. Then, as now, the derby was seen as the pinnacle of respectable men’s fashion—acceptable for dinner wear with a tuxedo or business attire. Of course, you can’t judge a book by its cover, and there’s no guarantee of actual respectability when wearing a bowler. Nonetheless, it is handsome evidence that not all mob affiliates were mugs in fedoras. You can easily work some retro mayoral swagger into your wardrobe with a derby by Christys or Dynafelt.

Oops. I mentioned antics. Big Bill’s were among the best. He once held a political debate with two of his rivals. However, instead of letting them attend, he replaced them on stage with two rats. He also claimed to have gone on an expedition to the South Pacific to look for rare tree-climbing fish. And to wrap things up, one of his classic promises was to punch King George V of the U.K. in the nose in the event they ever met.