First and foremost, before you pick a style know what`s going to work for you in different settings and situations. Headwear that cover the ears are considered less formal than hats that leave them bare. Crowned hats like Fedoras, homburgs  or bowlers are more formal than soft-tops hats . The thicker and softer the material, the less formal the hat. Thin, stiff felted hats are the `dress` options, while thick, woven materials  are informal.

Wool newsboy/flatcaps

Flat wool caps with a short brim are a go anywhere style for the winter months, they can be worn in thicker wool. These are basically indistinguishable from the  fall /spring styles, apart from the thickness, and are great  for  someone who wants to look stylish during a short time outside. However, in a bitter cold, the lack of ear, or neck protection makes them an insufficient source of warmth for any real length of time.

Military Cold Weather Headwear

There are some great options out there is military surplus stores, especially from the armed forces and other cold climate countries. These tend to be unique and functional. The styles often look strange to American eyes.
Finally, it`s not necessary to our many hats. A man with several scarves, for example may not have much use for a neck gaiter-though the gaiter is more portable and tucks easily into a pocket in a way that scarf doesn`t. The key is to know your options and to pick a few that work best for your wardrobe. And if needful, visit your cloth stylist to aid you in choosing a good colour for your complexion.Don`t get stuck relying on the same worn-out stocking cap all winter long. Yea, it does not look  good with your dressier clothing and you  will be cheating yourself of both warmth and style.