Depends on the overall match of the outfit; if I am wearing patterns, yes. I want shoes/bag same. And for very dressy events.
If I have a monochrome going, the bag OR shoes can be an accent, not both. I have sooooo many shoes and enjoy red or multicolor leather or blanket boots and feel matching bags would steal the effect.
If I am going with 2 colors in skirt and top, shoes match one, bag the other.
Other times, it's a hardware or texture match but color coordinate.
haha sorry long answer
short answer- sometimes when I feel like it
~ mood dresser