I'm glad this discussion is on. I'm very particular about matching fragrances with the weather. I understand not everybody does that. Some people insist, "I wear what I like, when I like" and I accept that. As for me, mood, weather, and dress style are the determinants.
Specifically for summer/spring rainy days I love:
Aramis 900 for the green/herbs
Aramis Devin for the green/herbs and leather (it's not overpowering like Yatagan). To me, both create the appropriate green/garden/country mood that I associate with that type of weather. Both have a balance of delicate florals (a hint but almost feminie) and boldness (dry in 900, just enough leather in AD).
Guerlain Vetiver--at once fresh and warm. I especially like to have it on during summer days when the weather turns cloudy and humid, just before a summer storm, sort of an incongruent hot/cool.
Still, I could wear other things if my mood changes but these came to mind first.