Man’s guide to cold weather hats

Who ever said seasonal fashion was for women? Men live in a progressively liberal world nowadays where it’s encouraged for them to look good, feel good, and maintain a lifestyle that puts effort into the way they dress and style themselves.

Where this summer has brought short shorts, floral t-shirts, and aviator sunnies, this winter brings yet another focus on a selection of cold weather hats that are not just warming in the wintry months, but also timelessly fashionable and sophisticatedly masculine…


‘The Watch Cap’

You probably already know this hat as a ‘tuque’ or a ‘beanie’. The term ‘watch cap’ derives from the military that describes a hat designed to give maximum warmth, hence the symmetrical shape and double layering that covers the entire head, from the tip of the crown to the base of the ears. They’re usually made of knit material to provide a snug fit.

Choose this… if you’re going somewhere very, very cold, and you value practical warmth over formal style.

‘The Flat Cap’

Flat caps are a notably traditional style hat that can be traced way back to the 14th century. However, you probably recognize them now as an iconic staple of the British working-class. They’re identifiable by their capped round top and stiff front brim that gives them the distinguished flat look. They’re usually made of cotton, wool, or tweed, and lined with linen for extra warmth.

Choose this… if you want a traditionally fashionable cap that can be worn on nearly every occasion.

‘The Stormy Kromer Hat’

This style of hat originates from a train engineer who goes by the name of, you guessed it, Stormy Kromer. After suffering from the harsh cold winter months on the trains, and noticing that his cap would frequently blow off his head due to the winds, Stormy asked his wife to modify the cap and make it a better fit. She ended up making what we know now as the iconically padded and tightly fitted ‘Stormy Kromer’ cap.

Choose this… if you want a hat for a casual look that has a warm and snug fit.

‘The Aviator Hat’

The ‘Aviator’ style winter hats as you know them were first designed for military pilots in order to keep their ears and chins extra warm during cold high-altitude flights. They usually have an extra thick top and a strap that can be buckled in to keep your chin warm, too. They have now also evolved into ‘Trapper’ hats that feature fur or a wooly material in the lining and at the front forehead area too.

Choose this… if you don’t mind looking a little silly to ensure your ears are kept extra cozy.


‘The Dress Hat’

The two most popular styles of dress hats are bowler hats and fedoras, and both of these sleek modern designs can be found with thicker felts and materials designed to keep you extra warm in the cold weather. Some have an extra woolen lining inside, and others have an ear warmer draped down the side. Generally, dress hats are super dapper, perfect for when you want to pull off a bold and sharp masculine style look.

Choose this… if you want a hat for a formal occasion and want to look smart, sophisticated, and elegant.

So there you have it – five different varieties of winter hats to choose from, and each one of them different. Which one is for you? It all depends on where you’ll wear it, what you’re wearing it with, and whether you want a hat with style or substance – or both!