You look like a pilot, please explain.

This sentence means that you have a good relationship with women. It is mostly used to tease and make fun of, but it is not malicious.

This sentence came from a little joke in private with a friend. The impression was that someone had a bra thrown on his head. Another person happened to see it, and he sarcastically said: You are quite like A pilot. It's okay to make jokes, but it's not very suitable to say it in a formal or public setting.

The hats worn by old-fashioned pilots in the past had two split lenses, which were large enough to cover the eyes and shaped like a bra. So this sentence was cut out as a joke. There was no negative meaning of ridicule, just ridicule.