Whet e-mailed me with a fashion dilemma: "Now that it's getting cold, I'm looking for a hat that will keep me warm and not make me look like a doofus—something a bit more fashionable than a beanie, more elegant than a hunter/bomber hat."
Here are his finds so far:
A wool hat from Orvis. A little too Elmer Fudd for my taste.
A driving-style Kangol cap with ear flaps. I do like the flat cap, which has a certain vintagey elegance. But it's meant for wet, chilly English winters, not an icy wind coming off Lake Michigan. And the earflaps on the Kangol ruin the effect. It's like wearing an anorak over an evening gown.
In the winter in Chicago, you want your ears covered. And there's the rub. Unless you can pull off a trapper hat or want to try a fedora (in which case you run the risk of being that guy who wears a fedora), you're pretty much left with basic knit caps. (Which Whet said he wasn't particularly interested in.) Sadly, men have fewer options when it comes to real warmth. Those are the breaks. They make a dollar for every 77 cents a woman earns, but we get a wider variety of chapeaux.
Still, I did manage to find a few styles I thought most men could carry off, which all tended toward the same shape, a kind of brimmed cap.
The hat in the photo at the top of this post (the Sonoma tweed beanie, $8 on sale at Kohl's) and the Timberland cap ($40 at Macy's) are both knits but have a structure that's comparable to a cloth hat.
This version by Coal ($35 at Nordstrom) is a wool-acrylic blend that looks a little more clothlike (and also has the advantage of more subtle logo placement).
A slightly more rounded version from Calvin Klein ($40 at Macy's) has an appealing resemblance to vintage baseball caps.
Guys, what are your solutions to this cold-weather style conundrum?