Cabbie hat, duckbill, newsie or flat cap. The names for this specific hat are about as rangy as the colors and fabrics used in their design. Traced back to parts of England and Southern Italy in the 14th century, the hat's provenance is steeped in sartorial expertise. And as the weather turns, a comfortable, warm hat becomes less of a statement and more of a necessity. The fabrics used in their construction range from heavy tweed to lightweight linen, but the most popular—as well as the most effective—are the wool and tweed styles with a silk lining. A neutral color will provide versatility for any outfit you're going for; be it a jacket with blue jeans or a full suit. The beauty of the driver's cap is that it looks great on just about every head shape. So give the knit beanies and wool 5-panel snapbacks a break, and embrace a refined Ivy look.
Mr. Kim, $235
Clive Hawkes, $110