“Being a milliner is akin to being a bartender or a shrink,” says Ellen Christine, a New York-based hat-maker whose creations have graced the glossy heads of some of the world’s most illustrious women. With 36 years of experience and a doctorate in costume design to her name, Christine crafts headpieces that artfully blend fantasy with practicality. Here, the grand dame shares her advice for good hat etiquette—and explains the psychological benefits of wearing one.

What’s the most important thing to consider when buying a hat?
Remember that a hat is meant to frame your face and highlight your features, especially your eyes. The most important thing about wearing a hat is making people look directly at your face when they’re speaking to you, not at the hat.

How do you cho...