I have lots of jackets (also a hiker, climber, skier, and backpacker) but there's only one I use on the bike. An Arc'teryx Accelero. I have two, but really only use one on the bike. The dead bird stopped making them so I'm probably about to order a few more, although I've had one for 7 years and it basically looks and performs like the day I got it.

I layer as appropriate for the weather conditions and the type of ride I'll be doing. Obviously I need less to stay warm on hill repeats day than I do for an LSD ride.

If it's dry and in the 30s, sometimes I wear a down vest over my jacket. The jacket keeps the down dry, and also having it as an outer layer at bike speeds keeps the down from being too warm. It works surprisingly well. The vest fits into a bottle cage very securely, I use a stuff sack to keep the vest clean.

I live in Wisconsin and bike all year (as long as the roads are clear of ice.) I found that if I wear an unlined wind-breaker over a fleece (polar-tek-wicking type) base, I can bike in cold temps under 20 degrees. If I feel the need, I'll add a t-shirt under the polar tek. Make the layers roomy. Give your body space for the body-heat layer. The polar-tek layer will wick your sweat off you, keeping your body dryer. Sweat is your enemy. If you get clammy-wet, you'll get chilled. Once chilled, you will have a hard time warming up. If you over-dress and get hot-sweaty early in your ride, you will be uncomfortable. Experiment. You can always add a layer, but once out there, you can't take it off.