Here are a few rules for winter headgear I found on The Art of Manliness’ website. This site should definitely be a bookmarked page on every gentleman’s desktop and devices. Anyway, check out the rules to keeping your crown warm.
Before you pick a style (or several styles — there’s nothing wrong with having a selection of hats in the closet), know what’s going to work for you in different settings and situations.
Bright colors like orange and neon green have “safety” associations. They’re worn by the more extreme winter sports participants to make search-and-rescue easier, and in many parts of the country they’re worn by hunters as well. So if you’re not a hunter or a pro snowboarder, think about toning it down a little.
Colors that aren’t safety-neon but still have bright, primary tones and shades (reds, blues, etc.) are casual, sporty winter-wear meant for leisure activities like skiing and snowboarding. You can wear them on weekends, but you probably want something a little nicer for the commute to work or evenings on the town.
Dark colors and earth tones are the dressiest: blacks, grays, browns, and so forth. These tend to have the most “go anywhere” ability — you can wear them on the ski slopes or between the taxi and the opera house door.
In addition to color, the style of the headgear affects where it can and can’t be worn:
Hats that cover the ears are considered less formal than hats that leave them bare. However, if the temperature is freezing, I don’t care if I’m wearing a tuxedo. My ears will be covered!
Crowned hats (fedoras, homburgs, bowlers, etc.) are more formal than soft-top hats (stocking caps, newsboys, etc.).
The thicker and softer the material, the less formal the hat. Thin, stiff, felted hats are the “dress” options, while thick, woven materials are informal.
Accents like pom-poms, fringes, and other dangly bits are always low-formality, and a bit silly to boot. Avoid them unless you’re trying to look obnoxiously cheerful and high-energy.
Most men own at least two options: a thick, practical cap for day-to-day existence outside in the winter, and a more formal, less-warming dress hat for short walks between transportation and a dressy setting like work or theater.
Now that you’ve got the basic rules on winter hats down, let’s take a quick look at some of your options:
For the list of options, visit The Art of Manliness.