For wet and cool / cold conditions, look for something that will keep you DRY as top priority. Anything that starts out warm and winds up soaked isn't going to do you any good. Waterproof often means that it's not breathable, which can make things too hot and steamy. So look for any kind of ventilation in the form of wicking material or mesh. For example, a light "wind" vest or jacket may have mesh at the sides and/or back, but the front is more resistant to the elements, where you'll get the brunt of the water and wind. Same for tights that will have tougher stuff on the tops of the thighs but will be breathable elsewhere.
Good gloves and booties are probably the best to go with. I personally like neoprene, but it can get really hot. Neoprene toe warmers and then some duct tape under your soles in your cycling shoes to plug the ventilation holes there might be good for stuff on the warmer end of the spectrum. Pearl Izumi makes decent booties and toe warmers. I like Specialized's neoprene gloves, but your hands will sweat like crazy. They will stay warm even in sub-freezing, wet conditions, so the sweat is worth it to me. Keeping feet and hands comfy will go a long way towards making your ride more pleasant. Next would be to protect your core (like with the vest or a jacket with windstopper stuff on the front). And a cap or beanie. A cap with a brim will help keep water out of your eyes, but make sure it's not too floppy or it will sag into your vision when it gets wet.
You might also want a clip on fender.



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