Q&A for How to Choose Hats for Your Face Shape

A gentleman always takes his hat off when he steps inside. A lady usually leaves her hat on as it is part of her outfit.

Depending on cultural customs, the hat can be kept on when greeting other meeting participants, if the greeting is done with a handshake manner. Recommendations in the 'gold-period' of hat wearing was removing the hat in a nonchalant manner before shaking hands with someone, preferably so that the person in question does see the hat removal. This signaled dignified respect without theatrical showmanship.

I would suggest a fedora, or beanie. However, a wide-brimmed sunhat might work as well.

It depends on what you like. Try a fedora, telescope style cowboy hat or something like that.

Flat-billed hats normally work well.

Try a straw garden hat or a small fedora. Avoid very small brims and choose something else over a beanie.