Handbags are my most expensive purchase. I won't tell you much I spend out of embarassment, but it's enough that I refuse to buy anything super colourful that might clash with my wardrobe. Moreover, each bag serves a function and no two bags overlap in function (yet). As a commuter, the look, durability, and design of bags are extremely important to me. I want bags that work well in professional, social, and black tie contexts, The bags should also hold my items securely, and allow me easy access to them.
At the moment, I own a blush wallet clutch with a chain, which I used daily for a long time; a navy suede crossbody with gold buckles, which hasn't been used in many months; and a black leather Le Pliage, which is used frequently.
The bag I use depends not on the colour of my outfit, but how I want to carry my gear. Since I've temporarily returned to knapsacks, I don't use my Le Pliage as often, and in fact, haven't been using a purse at all. My love of crossbody bags has blinded me to the fact that they are responsible for the buttons coming off my jackets.
My next bag, currently en route, is a tiny black satchel with feet and an optional crossbody strap. It looks like the perfect bag for my lifestyle, but is super expensive, and I haven't been able to find its equivalent at a lower price point.
ETA: The new bag on route can be found much cheaper in cobalt. I have agonized over whether the price difference for a colour is worth it. Unfortunately, it is. I don't want something that clashes with purple, or that looks too casual at weddings.