Preface: I get no money from this, I just really like these products.
I hate the summer. It's too hot and there's no way for me to get away from it other than running at 4am. Winter, on the other hand, can be relatively delightful if you have the right gear. As someone who has run all through three winters in the Northeast, here is the gear that gets me through:
You absolutely must get some solid winter socks. If you normally run in crew socks, you can probably stick with the same ones year round, but, as someone who wears ankle socks if not every inch of skin needs to be covered, I buy socks just for colder months. This year I've been really enjoying the Smartwool PhD Run Cold Weather Mid Crew Socks. I've also got a few pairs of the Darn Tough Vertex socks. It's hard to go wrong with either brand.
Generally, I just wear normal running shoes. Sometimes winter does not let you. Over the past few years, I tried using Stabiliciers, but, in addition to sometimes falling off, they did not dig into and grip patches of ice, so I would still slip. This year, I decided to buy a pair of the Salomon Speedspike CS. Like I mentioned in my post on summer running gear, I love my Speedcross 3 W. These had almost the same fit but with spikes. And the spikes are small enough to really dig into ice. A few days after I got them, I had a 14 mile run in 4°F with snow and ice on most of the ground. They were fantastic in the snow and ice and perfectly acceptable on the street. I also didn't get any blisters, despite them being brand new shoes.
Alas, my favorite jacket is now two years old and I can't find a place where they sell it. For reference, I love my Nike Shield Full Zip (near the bottom of the post). The key is to find a good water-resistant and wind-resistant jacket. The Nike Shield has served me well for the past two years, keeping me warm without even a base layer down to 10°F. If I was getting a new jacket right now, I'd probably try the Oiselle Flyout Jacket. But the good thing about jackets is that, even though they cost a good deal, they last at least a few years.
I love Oiselle's Plya Reversible Beanie. It's warm, lightweight, and reflective. For super cold days where I need some face cover, my favorite is the Oiselle Wazzie Wool Neck Gaiter. Like most neck gaiters/balaclavas, you probably don't want to run with it over your mouth the whole time. However, this one is so warm that I could put it up over my nose for a minute or two to warm it up and then put it back down around my neck for the next 20 minutes.
They stopped selling my favorite winter bottoms, but my second favorites are the Oiselle Tech Suede Tights. I actually wear these out and about more than I do for just running (again, second favorite), but they are pretty warm and do well down to about 20°F. Below that, I layer them with Arc'teryx Trino Tights. Secret: they aren't actually tights... more like pants. Usually, for 5-20°F, I wear them with shorts or normal tights. Below 5°F, I layer them with winter tights.
I've become such a dork for Oiselle. My absolute favorite base layer is the Oiselle Wazzie Wool Baselayer. I wear it while I'm running, while I'm working, all the time. It's so delightfully warm and comfortable without being too warm. If it's too warm for my jacket and too cold for a tank (between 25-40°F), this is what I'm wearing.
Well, that's me in the winter.