Quote:
"So with that being said what would you hike in if the weather was cold enough to require a jacket and maybe a chance of rain?"

I don't think you can find a clean consensus on this; different people will have different (all entirely "valid") preferences.

It depends in part on your expectations, and in part on your metabolism and just general physiological ("body") response to hiking in differing weather conditions. I've had good luck with light shell (water resistant or not depending on conditions) coupled with either a synthetic puffy garment (I love my Montbell thermawrap vest) or synthetic "fleece" type.
If you like hoodies, rather than a cotton one, try something along the line of a Patagonia R1 Hoody. They can be a bit of a PITA to pull on and off, however, or at least mine is --- just seems to be a lot of friction between the hoody fabric and the shirt I'm wearing underneath (and mine seemed to come sized a bit on the small size).

What I particularly suggest, or at least something I like to do, is go a bit lean on core body warmth and a bit heavy on layers to protect the extremities. I.e., in cold weather I like to start off with my core cool, but stout mittens over thin liner gloves, earbags and a hat under a polypro warm hat. Then as I warm up I pull off the warm hat and perhaps the mittens and stick them in pockets without having to stop to adjust. Certainly in this context having a deep or full-length zipper on core (torso) clothing is very nice.

I think that finding the right mix for conditions is something we each have to grope our way towards individually --- I know that some clothing combinations that seem right for experienced friends wouldn't be right for me.
_________________________
Brian Lewis
http://postholer.com/brianle