The turtleneck's awesomeness was of course initially established by the film Bullit (1968) and solidified shortly thereafter with Shaft (1971), but a lot of us are still deterred from wearing this highly flattering staple due to comfort issues. The late Mitch Hedberg once said that "wearing a turtleneck is like being strangled by a really weak guy, all day", and you don't need a particular sensitivity to wool to not tolerate itchiness around your neck for very long. The solution to the former problem is a turtleneck sweater; the looser knit will feel a lot less constricting while still keeping you warm. And to the latter, just avoid your typical wools and opt for cashmere or a soft blend. Above right: lightweight cotton-cashmere, great for layering, from Lands' End Canvas [$60]. Below right: thicker 100% cashmere with great ribbed trim and cuffs, from L.L.Bean Signature [$189].