Neal Caffrey wears a fedora most often in White Collar
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A beanie. Blue collar construction workers and mechanics wore them to keep their hair out of the way. The brimless hat was preferred as it would not abstract their vision.
A Trilby hat or Deerstalker hat.
green and white striped bucket hat
Stetson Diamond Jim with a custom hat band.
Yes a black hat with a red, white & blue beaded band