Men’s Fashion Advice: More on winter hats

Getting around a big city in the winter can be tough for even the most hardened urbanite. Public transit in January isn’t for the weak. Luckily bundling up doesn’t have to mean looking sloppy. Check out our recommendations for three classic hat styles in three classic cities this winter:

New York

New York’s paperboys knew how to stave off the bitter cold on the city streets. The newsboy cap features eight panels with a button on top and a stiff peak in front. Just like New York, it’s known by many different nick-names including the Baker Boy, Apple Cap, Eight Panel, Cabbie, Fisherman’s Cap, Pageboy, and Jay Gatsby (from The Great Gatsby). The newsboy cap is versatile and works equally well with a sport jacket or a sweater and jeans.


They don’t call it the Windy City for nothing. Chicago’s skyscrapers compress the icy blasts that roll off Lake Michigan and send them barreling down the streets. Waiting for the “El” on a blustery February morning can test the most hard-core Midwesterner. The trapper hat provides maximum protection since it sits low on the forehead and features lined ear flaps. Named for the fur trappers who created the style, the first trapper hats were leather and lined with rabbit or fox fur. Today’s trappers can be found in synthetic materials as well but nothing beats the effectiveness of nature for protection from the extreme elements of a Chicago winter.

San Francisco

Winter in San Francisco may seem mild compared to more northern latitudes, but there’s something about cool fog that produces a bone-deep chill. A trilby hat is the perfect solution for San Franciscans who want to stay warm and look tasteful. Trilby’s are often confused with fedoras but can be distinguished by the shorter brim, which is angled down at the front and slightly turned up in the back. The hat’s name comes from a play titled Trilby, where a hat of this style was worn in the first production and immediately became known as “a Trilby hat.” If a San Fran resident likes the shape and fit of a trilby, this style is also usually available in lightweight straw for sun protection in the warmer California weather.

What style works best for winter where you live?

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