Q: My brother and I have an ongoing debate I'm hoping you can clear up. When is it appropriate/ not appropriate for a man to wear a hat?
A: Not only do I conduct a lot of business dress code seminars, but from time to time I am asked to teach etiquette classes. So this is a question that frequently arises, especially with the recent popularity of the TV show Mad Men, depicting an era during which hats trended toward dapper styles, and baseball caps were reserved for actual baseball players.
In the 1930s through most of the '50s, a man wasn't considered fully dressed without a hat. But by the 1960s, hat wearing fell out of favor, partly as a result of longer hairstyles, cars with lower roofs, and resistance from some World War II vets weary from wearing helmets for so long. JFK's habit of not donning a hat was seen as the final blow to the trend.
In large part to Mad Men, hats are experiencing a revival, but unfortunately the rules surrounding hat wearing (and removal) have not followed suit. Generally one shows respect to others by uncovering indoors, but "indoors" can be a subjective term. All homes, churches (unless required by the religion) and restaurants should be hat-free. Public spaces, like train stations, airports, hallways and elevators, are considered hats-optional, as are sports arenas. However, old school gentlemen (a lost breed) will still remove their hat when a lady enters an elevator.
Ladies are mostly exempt from hat etiquette, with the exception of baseball caps. It has always been accepted that if a hat is considered part of a woman's outfit, it may be kept on. In the spirit of equality, this allowance is now being extended to men as well, to the pleasure of vendors such as J.Crew and Gap, who have included fedoras and pageboy caps in recent collections.
But to all, wearing a baseball cap backwards is never appropriate!