You're going to want a few specific things, including a party hat.
One of the toughest questions we get is how to dress for the cold. What makes it difficult isn't the clothing itself, but how different everyone is in the cold. On the very same Friday Night Lights ride, you could very easily see one rider in summer riding shoes and gloves, knee warmers, and a light jacket, another rider in winter boots, coat and gloves, and still another rider layered up with a big jacket, snow pants, and a bike or ski helmet replete with goggles. Part of the winter riding process is finding what works for you, but here are a few good places to get started.
Base layers. It's the best investment you can make, to be honest. Cotton t-shirts are an especially bad idea, absorbing sweat, getting wet, and making you more and more cold, even if you're riding nice and steady. A good GORE long sleeve base layer helps wick sweat and keep you dry, and GORE, like many brands, offers a thinner, lighter 'all season' version as well as a 'Thermo' fleece version for even colder weather. Depending on the temperature and your own body temperature, you might only wear your jacket over it, or a normal cycling jersey. Unless it's under about 20 degrees or very windy, I usually wear a short sleeve cycling jersey over a my base layer, with a breathable GORE Phantom 2.0 jacket over it. I like the extra pockets of the jersey; it's a good place to put your phone or keys, instead of in the coat pocket, which might can be dangerous if you're digging in there with gloves on and drop something important.
Gloves. There are two kinds of people in the world, people with cold hands and people with cold feet. If you're one of the former, riding even for a short amount of time can be a literal pain once it's below freezing. I've spent a lot of money not fully solving the problem, and it wasn't until I finally bought some 45NRTH Sturmfist 4s that my issues went away. They are pricey gloves, but even when the temperatures hit the single digits, my actual digits are still okay. If you'd rather wear a lighter gloves, getting a Bar Mitt or 45NRTH Cobrafist is also a great option. Those big covers are bombproof protection against the wind and cold, and if those don't work, you might not want to be out there.
Boots. So your hands are fine, but you're worried about your toes every time you go out. Don't worry, you don't have to have thoughts of Ernest Shackleton before every ride. 45NRTH makes the Japanther, Wolvhammer and Wolfgar. Think of them as spring/fall, then winter, then frozen hellscape. The Japanther is solid for fall and spring riding, and if you have warm, hearty toes, you might be able to get away with them all winter. Wolvhammers are Ec's go-to winter boot, and is the safest bet if you have any issues with cold toes. The Wolfgar more than suffices for winter riding, Mars landings and, with a properly altered sole, could make a very hip looking snowboard boot, too.
Neck Gaiter. Keep your neck warm, your face warm, and look effortlessly cool doing it. 45NRTH, Surly, Louis Garneau and Smart Wool all make some very nice options suited to what you need. A merino for cold days, a synthetic wind stopper for the open road, or something a bit thicker for those really blizzard-level outings.
Dress up, dress warm and we'll see you at Timber Ridge, 6:30pm for Friday Night Lights!