Complexion
Just like suits, men of any complexion can often get away with a basic black or grey hat and they will blend in just fine. That being said, some colors do compliment some particular complexions. If you have a fair or pale complexion, rock the aforementioned dark blue or grey. Men with a more olive or tan complexion can experiment with browns, greens and other similar earth tones. Men with a dark or deeper complexion can work browns and blues.
Material and Matching
Let the season and occasion be your guide when selecting material. Spring and summer months lend themselves to straw toppers that let the head breathe in that summer heat. They are also acceptable for more casual events like that wedding, pool party or rooftop happy hour. Once you get into the fall and winter, it’s best to go the felt or wool route since it will provide more warmth. These types of fedoras are also more widely accepted at formal events or work related occasions (provided you like to channel your inner Don Draper). Finally, don’t underestimate complimenting your hat with your clothes. Hats in various shades of brown will compliment brown, green and even dark blue shirts, suits and coats; grey hats work well with blues, blacks and greys; and blue hats work well with blues and greys.