Well, I live in a place where we have four very distinct seasons.. and about 6 months of it is winter.. LOL!
My lime Hailey is for spring/summer. When I think spring/summer, I think lime, bone, white, yellow, pink, peony, coral. I plan to carry her all summer except if I go out at night, or the lime clashes with what I'm wearing.
My walnut Madison screams fall/winter to me! I plan to use her until my birthday (middle of March), then switch to Hailey until September. Fall/winter colors to me are: brown, espresso, dark green, black. Most other colors are year-round colors to me: silver, gold, cinnamon, red, teal, blue, cherry, cranberry, amethyst, purple.
Year-round bags for me are my black Sabrina and silver Glam Tote. I will use those for the appropriate occasions or desires as necessary.