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A Guide To Men’s Winter Hats

Welcome to the first installment of our winter accessories series – a guide to men’s winter hats. With October finally showing itself and a bit of a chill setting in, those of us in Philly and New York City know that the freezing cold weather is only a couple of weeks away. This guide will give you an overview of various hat styles and how to wear them.

Casual Men’s Winter Hats

By casual, we mean a hat that you can wear with anything as dressed up as a sport coat and jeans and as dressed down as a pair of custom joggers and a puffer jacket.

Scally Cap

man in grey tweed capAlso known as a newsboy hat or a flat cap, this is a simple hat that works particularly well on taller men since it doesn’t “heighten” the wearer too much. Available in a wide variety of colors and patterns, they’re great in simple grey, navy, or brown. If you like something more eye-catching, there are plenty made with strong weaves and windowpane patterns reminiscent of Harris tweed sport jackets.

Baseball Cap

mens wool baseball capThough not technically a “winter” hat, baseball caps are so ubiquitous that they need no introduction. While we certainly appreciate supporting the home team (Go Phils), baseball caps are most versatile (and least divisive) when they’re done in simple, solid colors like navy blue. Paired with joggers or casual jeans and a sweatshirt, they’re a great solution to the “I just rolled out of bed and need to run some errands, what do I wear?” dilemma.

Beanie/Skull Cap

man in cream hatThe quintessential winter hat, the beanie is what you wear when you really want to keep warm. Typically available in wools ranging from beefy lambswool to luxury cashmere, they do a great job of holding in your body heat and covering your ears, which is clutch in the cold weather. A pom pom adds a little whimsy.

Bomber Hat

mens plaid bomber hatThe bomber hat is more function than form. It’s almost costume-y, with long ear flaps that provide extra coverage on the coldest days. Don’t try to dress this up – keep it casual with sweats, jeans at dressiest.

Dressy Men’s Winter Hats


man walking in snowstormThe Fedora is a classic men’s hat, featuring a sizeable brim, a tall-ish crown, and a grosgrain band encircling the crown itself, often finished with a discreet bow. Back in the first half of the 20th century, men wore these types of hats almost as a rule when they were outdoors. In fact, Mike, our Operations Director, has a distinct memory of a conversation with his grandfather wherein the latter mentioned that he was glad men didn’t wear them anymore (this was in the 1990’s).

While they’re still somewhat rare, they can really add an element of old school panache to an outfit. Throw one of these on with a suit and tie – a grey, navy, chocolate, or black felt version are great starting places.


frank sinatra in suit single breasted coatTrilby hats are often mistaken for fedoras. They’re very similar, but trilbies have a shorter brim – in headwear parlance, this would be referred to as a “stingy” brim. A little more casual than a fedora, these work with jeans, vests, and sport jackets. If you’re a smaller-framed man (particularly with narrower shoulders), a trilby will work nicely for you.


lester young in a porkpie hatThe porkpie hat is characterized by a small lip around the crown and features a snap brim. An all-around “rounder” hat, it looks best on taller, slimmer men. These were very popular in the 1930’s among college students. Fun fact – jazz saxophonist Lester Young was known for wearing these. When he passed away, legendary jazz bassist and composer Charles Mingus wrote Goodbye Porkpie Hat in his memory in 1959.


There are many more hats available on the market than are listed here, but this is a good start for someone just beginning to build a collection. Curious to start honing your image? We’re here to help. Call 215-310-0219 or email info@henrydavidsen.com to start a conversation.

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