For 3-season tours:

Head:
1 cycling cap
1 ski cap
1 helmet

Tops:
2 long sleeve light weight shirts
1 midweight half-zip fleece sweater
1 hooded down jacket if cold temps expected
1 rain jacket

Bottoms:
2 padded cycling undies
1 boxer-briefs
1 shorts that go over undies
1 pants
1 rain pants

Hands:
1 pair long finger runner's gloves

Feet:
2 pair wool socks
1 pair sneakers
1 pair rain booties