I usually go white or black hat. I dress pretty colofully, but I can never find hats that match my shirt. If the colors don't match exactly, it bothers me. Standard hat/belt, go colorful on the shoes, shirt, pants.
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It has to match or accentuate something else in the outfit.
^^This^^Ha. I'm not smart enough to put my theory in to hats in words without sounding like an idiot. But I generally will use my hat to blend together my pants, belt and shirt. Sometimes is just a straight match to the shoes, sometimes the belt, sometimes its to play off the shirt, belt, shoes. Sometimes I'm trying to pull accents from either my belt or shirt to make those stand out more...I have a lot of theory that goes into it..lol
It has to match or accentuate something else in the outfit.