I generally associate more poppy/cheery/light-hearted music with summer, and calmer/deeper sounding/symphonic stuff with winter. Not that I won't listen to any kind of music any season, but some things just seem more apt for the season.

A few shuffled examples:
God Help The Girl - God Help The Girl - YouTube
The Dirty Heads - "Lay Me Down" feat. Rome (Sublime) - Executive Music Group - YouTube
Rilo Kiley "The Frug" - YouTube

Edit:
Quote Originally Posted by Shorty View Post
Rilo Kiley, Sublime
oh snap