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I'm not at all a gearhead, so I just wear whatever I have, always keeping that whole “layers” premise in mind, of course. As I've hung out more with my gearhead husband, I've started to appreciate some of the fancier clothes, and I do have some stuff that I've picked up at REI garage sales (a sale for coop members that has super cheap stuff that's been returned or is not quite perfect enough to sell at full price) or used.
Waterproof, windproof jackets are crucial to being really comfy in cold and wet weather. Obviously, you want them to have a full zippered opening, so that you can easily take it off without having to pull it over your head, when you are too warm.
Tights are great, as are padded biking shorts/tights. I don't ride long enough distances usually to make it necessary to wear the padding, but bike tights/shorts are comfy and convenient, if expensive, and I do wear them if I'm going to be biking for a longer time than a short commute.
Gloves are an absolute necessity, as far as I'm concerned. I wear biking gloves in the warmer months, and plain old stretchy knit gloves (that you can get at any department store for a few dollars) in the cooler months. And then in the really cold months, I either put knit mittens over my knit gloves, or wear fancy sports mittens that are mostly windproof and waterproof. Mittens are definitely good for keeping your fingers warmer than gloves, and the lack of dexterity isn't such a big ussue on a bike.
For pants in cold, snowy weather, I often wear cheapy snowpants that I can pick up at a thrift shop for a few bucks. They have a flannel lining, and a polyester top layer. They are not at all waterproof though. So when it's really wet and cold, I might wear my fancy REI waterproof snowpants.
And don't forget lights! I have at least two headlights (one as backup) at any given time. One is a simple LED head-lamp mounted on my helmet, and the other is an LED headlight with rechargable batteries. I've also got one of those dynamo (wind-up) powered flashlights that you can get at some department stores that I'm planning on mounting on my bike so that I don't have to worry about dead batteries. Unfortunately, the dynamo light isn't very bright, so it's mostly just a backup at this point. If I was rich, I'd get a hub dynamo lighting system installed, but that's not likely to happen in the near future :-) I've also got a little red blinkie attached to my courier bag, for the rear light. I only have to recharge the batteries in that a couple of times a year, which makes life a little easier.
For more cold weather tips, check out the wonderful Ice Bike website at: http://www.icebike.org/
Peace, Love, and Bicycles,
Turtle
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