I can post my notes so far this year... but one thing to consider that most people are overlooking... as your fitness increases, your "casual" pace increases, that means more watts to the ground, and more watts to the core / body heat. Also, as your body fat decreases, your natural insulation decreases.

If you used to commute at 150w, but now you casually roll along at 250w, you will require much less clothing to stay warm.

That said, my fingers are still cold, no matter what anyone tell me. So far only numbish, but truly numb is just around the corner.

This is what I have so far: (all shorts and tights are Hincapie bibs)

60-99 shorts and ss jersey (maybe arm warmers)
50-60 shorts, ss jersey, *arm warmers
45-55 shorts, *knee warmers, *medium base layer, ss jersey, *long finger gloves
40-50 *polar knickers, short sleeve jersey, *team jacket, *warmer long finger gloves
35-45 *polar knickers, *long sleeve jersey, *team jacket, *warmer long finger gloves (maybe winter gloves)
30-40 *polar tights, *long sleeve jersey, *team jacket, izumi winter gloves (probably with liners), thin wool ski socks, arenberg hat (for ears)

Under 30 - still TBD - but I have more (and thicker) base layers, knee warmers (under polar tights), balaclava, lobster claws, thick wool ski socks, and north wave farenheit mtb shoes in reserve.