I think I decide on which bag I'm going to carry based on my needs and where I'm headed. College: charlie backpack/ gotham tote. Shopping/ errands: Rogue, saddle, dylan, etc...
As for colours... nothing about me matches
Normally I tend to wear darker colour handbags (brown, black, navy) in Winter. I live in jeans and also the weather tends to be quite wet and windy in the autumn/winter. I opt for my pastel colour bags in the summer/spring - it just suits the season, plus I tend to wear lighter colour clothing and dresses (no colour transfer!)
Accessories wise, such as purses and pouches, it just depends on what I feel like!
I have a rainbow wardrobe, and my mood for fashion changes TV every day. Some days I want to be edgy and wear black, some days I wanna be girly, some days I want to be boho. I hate to buy anything that can only be used in a single time of year.
I live on the Gulf Coast. The only seasons we have here is hurricane season and gnat season. I wear what I want when I want. Suede in the summer and white in the winter, I don't care.