Whether you're talking about the men's or women's segment, most people will agree that fashion rarely mixes with comfort. Most times, you only get one or the other, especially when the weather gets unfriendly as in the middle of winter.
Beanies are a quick and extremely inexpensive way to keep your head warm in cold weather. For something more mature fashion-wise, though, trappers might be a better idea than the beanie hats. They may not look any more cutting edge, but they're definitely much more rugged and insulated. Wear with the boot outfit above and you have a ruggedly urban look for even the coldest of cold days.
Thick, warm clothes are the only way to go during the cold days of winter, but that never has to mean that you go around looking like you're wearing a dead seal. Wear exactly the right style pieces so that you don't end up adding more bulk than is absolutely necessary. If you look at things the way a fashion-conscious man does, every single layer counts.