The Way You Wear Your Hat

Hat hair is the bane of my existence.  I’ve eschewed hats on subzero days to protect my vanity and my hair.  Last year I realized that being underdressed for  weather is more embarrassing than a case of hat hair that’s difficult to fix.  

Push came to shove, and I broke down and bought a navy Berglund watch cap from Askov Finlayson.  I’m not a fan of beanies because of their one-dimensional look.  I like watch caps, however, since their ribbed knit add a pop of texture to any outfit and their warm wool is practical on cold days.  The Berglund - named after The Bachelor Farmer’s head chef Paul Berglund - is made in Minnesota from lambswool, and features a subtle brass rivet that dresses the cap up.  I like mine enough that I might pick up the forest version this winter.    

Two winters ago, I bought a wide-brimmed Barbour hat.  The olive green hue and soft felt lent it a look that paired well with both formal and casualwear, plus the tall crown helped me avoid the plague of hat hair.  The sole issue with the hat is that I looked ridiculous in it.  I would never buy a trilby because of their negative connotations (plus they don’t look good on guys under 50), but the Don Draper fedora is not immune to the same level of condescension.  I’m not one to buckle to others’ opinions, but when enough people note that the hat wears you instead of the other way around, it’s time to retire it to the closet.  Perhaps I’ll brush it off again once I’m 30, an appropriate age for men to start wearing wide-brimmed hats.

As a child, I would steal my grandfather’s driving caps because I thought they made me look debonair and wealthy, like a distinguished man.  I experimented with this style in high school (with radical buttons on the brim) and college (with a half-baked version by H&M), and am considering adopting it again since it pairs better with tailored clothing than a watch cap.  A couple versions that have caught my eye are Fox Brothers at No Man Walks Alone and a beautiful suede version from Lock & Co. that Simon Crompton of Permanent Style wrote about this month.  The light chocolate suede pairs well with navy coats and Earth tones, while the heavy patterned tweed options from Fox Brothers are more versatile for everyday wear.  Either way, the driving cap adds a dash of rakish panache to a considered winter ensemble and keeps the head warm.

Hats: Askov Finlayson, Barbour

Bag: Duluth Pack