The Fedora - this conservative, lightweight fedora from Brixton Castor pairs well with jeans and a t-shirt. Avoid topping off your three-piece suit with it, or you'll end up looking like you just walked off set of the newest Gatsby film.
The Lumber Hat - similar to the fedora, this hat by G-star has the perfect sized brim. Not too small, not too large. Keep it cool, not nerdy by adding a vest to your outfit.
The Beanie - You can't go a day in LA without seeing someone rocking this beanie with a pair of Persol sunglasses. Not just for hipsters, this soft, slouchy cap from All Saints is the perfect headwarmer on a cool evening.
The Baseball Hat - You can never go wrong with throwing on the ball cap of your favorite athletic team.