Men’s Guide to Winter Hats

So we have yet to experience any terrible winter weather here in my home of Chicago, although we are notoriously known for our awful winter weather. The inevitable is looming, and I have already begun to invest in some staple winter essentials; above all being hats. Here are some of my favorite hats currently in my closet, as well as some of the styles I can only hope will make winter a little less frigid, and a lot more stylish. Looking good when you’re freezing cold can be tough, but it’s not an excuse not to!

Barbour Castleside Wool Beanie |  $59

This beanie is the perfect everyday winter hat to grab on your way out the door when it’s a little bit colder than you expected. Knitted and made from 100% wool,  it is crafted in Scotland where they know a thing or two about it being cold. This Fair Isle design styles a warm and cozy hat you’ll have forever. 

All Saints Charge Trilby Hat | $70

Made from wool, with a fully lined interior, this hat is perfect for dressing up a day-to-day outfit. Casual, but with a slight elegant flair, this is one of my favorites. Trilby hats never go out of style, and you must have one as a winter essential.

Zara Camouflage Hat | $17.90

This hat is not only functional, but it’s stylish too! The multicolor camo knit is a great everyday piece. Throw it on when you’re going for a run or pair it with a trendy leather jacket for a night out with the guys. 

John Varvatos Jacquard Knit Hat | $198

A crafted wool-cashmere blend, this hat is a fearless take on a classic style. Not many guys are bold enough to rock leopard print, but I don’t care because I LOVE it. Its sophisticated subtleness is what makes it so unique. I wear this almost every day. 

Ted Baker Charlie Knit Beanie | $75

Seriously, you can never have too many beanies. Girls have it easy with the long hair, but us dudes need to worry about our ears freezing off. This Ted Baker hat is awesome. The pompom adds a hint of whimsy to a cashmere-softened cable-knit beanie that makes for a smart seasonal staple.

H&M Wool-blend Cap | $12.99

Okay – not necessarily a winter hat, but this wool blend cap is a classic. Once you get over the vision of the ‘Newsies’ boys, you’ll wear this all the time. It’s the perfect way to dress up an outfit while looking like a old school newsboy.

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