Gesh there is a lot of gear to keep warm and carry in my pockets. On top of all the layers, one starts lookin' pretty prego! So what do I wear? I start with an Ibex wool bra, I/O bio glory zip or contact 2 top, depending on temps, followed by my RBH design vest, Montbell Nomad softshell, and then as temps drop I put on the Montbell thermawrap, which I also refer to as my honey, and when temps really drop I add my Mountain Hardware puffy jacket. I also carry one more jacket used for wind or wetness, and thats the top. Bottom gear starts with Pearl Izumi 3/4 bike shorts and either the I/O Bio 3/4 contact tights or full contct 2 tights, covered by Swix nordic pants which are over 10years old and I have finally wore holes in the seat.
In my pockets: spare headlamp which is the Princeton Tec Fuel, a set of spare batteries which include 8AA and 4AAA, tp, wetwipes, firestarter, matches, tool, aquaphor, chain lube, contacts, toothpaste, toothbrush, 4 packs of handwarmer, camera, and music player. The there is my pack which contains a 200 oz bladder, my Princeton Tec Apex Extreme, a pic to comb my hair, some barretts and eleastics, as well as a list of phone numbers, ID and cash-o-lah. In my pants pocket I carry a small knife, duct tape, and lighters.
This is also how I sleep outside. Fully dressed, with all the layers, water pack, boots on, all the gear in my pockets. My hands get really cold, really fast so I like to be able to just get up, stuff -n-go! This way I can start moving ASAP and get the heat generating.