I’ve said it before and I will say it again… there is NO trick to wearing a hat. It is like any other article of clothing, you have to find the right shapes and styles for your figure and character. Some men look good in flat caps, others don’t, some look good in wide brims, others need a stingy brim, some prefer traditional ribbons, others like colorful ribbons, some wear a feather and some don’t. The first step to getting into a hat is going to a real hat shop, one that features many different brands, preferably one that can offer customization as well, and one where their staff is comprised of knowledgeable Hatters, not simply sales associates.
Salmagundi Boston is a good start.
(Source: , via theclassyswede)