While the cold winter's air will drive many a fella to the warm embrace of a toque (or knitted beanie, for my non-Canuckleheaded audience), I've never been partial to them unless the temperature's dipped well below the fashionable limit, and a question of survival arises over style. A head condom, for lack of a better term, is called so for a good reason, and in my most humble of opinions the less we speak of it, the better.
(In fact, the toque is one of the few staples of dude-dom that is better served by a feminine touch; for every guy-gourd shoved unceremoniously in a knit skull-cap, making him look somewhat tick-like in appearance, the falling locks of a lady, blooming out from under or cascading down the shoulders, allows for the kind of visual contrast such a simple hat requires to really succeed as a fashionable item.)
The classic newsboy does have a retro-work-a-day charm, but be careful what outfits you match it with. A suit and tie must be colour checked to fit the generally earthy tones associated with the cap, the obvious exception being the black cap, which while going well with more looks, can be easily confused for the "classic" look of the private driver, and you may find yourself holding a great many doors.
For the man interested in a challenge this winter though, I suggest a pork pie (that is, if you haven't already settled on the always-charming fedora). A look that's suffered its fair share of ridicule over the years due to being characterized as somewhere between frumpy and ill-mannered, the pork pie, and its many variances, is a topper that demands confidence to be worn, but rewards its wearer many times over in individual look and charm. I for one have never seen two such hats worn in the same place, just as I've never seen someone wearing such a cap without a date on their arm.
But what of the more adventurous male? The kind of Trapper John who wears what he catches? The fur hat has typically been a staple of the Northern countries, hovering between real world practicality and PETA-rage inducing fur-lined flare (for the fun of it). While I wouldn't suggest going as far as the coon skin hat, the beaver pelt top, or overly-ridiculous coyote-fur (at a fetching $299), the classic Russian-inspired looks carry a cold determination to persists through the winter months, while looking ready to take in the Bolshoi with a Balkan beauty.