GayestManAlive

In the winter, your jacket is probably the LAST thing you want to concern yourself with. I've ridden in 0 degree days with 2 hoodies and 2 pairs of long john shirts and I was sweating my balls off.

In the winter, your feet and hands are the most important things to worry about. Your head too, but a knit cap and a face mask or a scarf takes care of that.

Your legs are constantly moving and generate a lot of heat so they don't matter. Some guys go all winter in shorts and a pair of winter spandex and are totally fine.

For the feet, there is really no good choice, unless you are riding clipless and can afford a pair of the gore-tex winter riding shoes like Sidi makes ($200+). I rode clipless last winter but instead I bought biking booties ($20) which were great but didn't keep my feet totally dry, as they go on the outside of the shoe which lets water in from the top.

If you are riding regular pedals, I'd suggest a pair of waterproof socks and multiple levels of NON-cotton socks. It's really a trial and error process. But remember, you don't want to layer so tight that your feet can't breathe. I think this is because it lowers the circulation in your feet as well as doesn't allow a cushion of heated air to surround your foot.

For gloves, they make special riding gloves, but a cheap pair of heavy winter gloves do fine. If your hands still get cold, throw on unerneath the thick gloves a pair of those cheapo thin gloves you can find everywhere. This is also good because if your hand sweat the inside of the thick gloves won't get wet, so you can easily dry them out when you get home.