Reddit mentions of Smartwool Men's Hiking Medium Crew Sock (X-Large, Gray)

The biggest thing I have noticed is that no one else has commented on letting yourself climate to the climate. As it cools off let your house cool with the outside. Personally I like a house in the mid 50's during the winters. This really lets your body get in the mode of heat conservation, while not required it does make going out far more enjoyable. As far as clothes here is what i wear.

Hat: It changes based on the year, currently rocking a generic knit hat like this. It covers my ears and keeps them warm.

Coat: This is similar to what i have as an outer layer. Nice and heavy, with a canvas shell to keep the wind out, as a bonus it is fairly water resistant. Under that layer one or two sweatshirts depending on the weather.

Gloves: This is fairly similar to one of my pairs of gloves, mine are older and more generic looking. Get several pairs of gloves, they take forever to dry.

Pants: You could get a pair of snow pants, and that would be the best if you are planing on being in the snow. If you are just shoveling or some other activity where you aren't planning on being in to much snow then jeans over sweatpants work wonders.

Boots: I believe this is the brand my boots are, similar style too. They are overkill unless you plan on being in the snow for hours at a time. Nice and puffy to keep my feet warm. Its important to keep your limbs warm as your body will slow circulation to the extremities if you start to feel cold.

Socks: Smart wool sock are a godsend, i swear by these things.

This gear is what i wear in the coldest of days out shoveling and generally fooling around in the snow. In most cases a couple of hats, couple of pairs of varing weight gloves, a good heavy jacket with some flannels or sweatshirts will serve you well. If you are living and working in the city its not a huge deal as you are never too far from somewhere warm. The most important thing to remember is that wetness and wind are what makes the cold feel cold. Beyond that it is just a case of being comfortable. winters aren't as bad as people make them out to be, a little forethought is all you really need. 90% of the times you go out full snow clothes will be complete overkill as you will be going to somewhere warm and only out in the elements for a couple of minutes.

Subnote about footwear, snow doesn't magically disappear from walking paths, and salt just turns it into mush. Make sure you shoes are waterproof.