5. Brent Black’s The Hat
The iconic brand of Brent Black has a second mention at this list. The Hat is known as the finest Montecristi hat around and is according to Black the result of a search for the finest Panama hat. It is made by famous milliner Simon Espinal who only makes 3 to 4 hats a year. The material is said to be lightweight and very durable. Estimated costs of the hat are around $100,000.