I think one of the most debated of menswear items over the past 2 years is the turtleneck. One can make an argument for pleated pants, but due to the level of difficulty and general lack of affordable slim, single pleated trousers my money is on the turtleneck. You can find a well fitting turtleneck in a lot of places, but so many guys shy away from them, in the U.S. anyway. For guys that prefer an understated look but at the same time don't want to get lost in the riff-raff, a slim fitting turtleneck is the way to go.
|Blazer and Socks-Gap|Turtleneck-United Colors of Benniton|Jeans-Unbranded Denim|Shoes-Sperry|
Not only can they be versatile and stylish, they are also functional in cold weather months. Nothing is worse than rocking a scarf and a cold gust comes through and finds that ONE gap in the scarf and chops you in the Adam's apple Liam Neeson in Taken style. Turtlenecks are tricky, though, because there are many variations. If you are new to the turtleneck game, going with cotton or a fine merino wool are your two best bets: classic, lots of places carry them, and they are easily layered under coats, blazers, and even overshirts. Chunkier turtlenecks are a little tougher for novices, but can be great too. Tweed blazers with turtlenecks is a collegiate classic, which I love in part because I live in a college town and work for a college.
"No socks with boat shoes" is one of those rules that you have to learn how to break. You can rock socks, but they must be the right kind of socks and the weather has to be appropriate (anything sub 55 is too damn cold for boat shoes even with socks). A nice, thick (but not too thick) camper/boot sock works well with boat shoes.