Thanks to an anonymous comment recently posted we'd like to address the issue of men's hats.  No, not that dirty, fitted, duck-billed baseball cap of your favorite college team that's seen its better days and covers the infamous bed head.  We mean a proper hat or cap that accentuates the true gentleman's attire and his overall personality. Take notes gentlemen: Hats are first designed for function.  Hats keep the sun, rain, snow and other elements off your head.  Hats are secondly designed for style. Buy a hat for how it will function in your daily life, and then buy it for how it looks.   With so many options out there this guide is by no means extensive and should be used as a primer for further research.

Formal occasions call for the Homburg.  This structured felt hat with a pinched crown and wide fixed brim has been seen on the red carpet, state dinners, and on the Godfather. The top hat which most men are familiar with but will never take the opportunity to wear is the ultimate in formal wear.  Reserve this option to wear with a morning suit to avoid sartorial disaster.

Homburg
Professional options for the office, travel, and outings with a lady friend include the classic Fedora worn by many of the most stylish men in the world.  Made of felt it features a high, pinched crown with a wide, flexible brim and wide hat band.  Find a quality Fedora at the legendary hat maker Borsalino.  Another option is the Trilby.  A sleeker version of the Fedora, this option is reserved for the man who wishes to make a fashion statement while not being taken too seriously.
Wool Trilby

Popular casual options are the driving cap and the newsboy cap.  Both of these flat crowned, flexible, and functional men's caps are bred and born to play in.  While mostly made of wool, or cotton, they can be had in cashmere and other fine fabrics. They are ideal for weekend wear in the city or country.  While it may be counterintuitive; the casual, dressed-down aspects of these caps will actually add an element of sophistication to the gent's wardrobe while still being playful.

Driving Cap

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