I've been thinking a lot about matchy-matchiness, particularly matching shoes to bags, ever since Smittie's post about white and blush bags. I'm not a "bag person" but I would like, at some point this year or next, to add a convertible-crossbody bag that isn't black, mainly to add some "pop" against my mostly black and navy winter outerwear. My only crossbody bag right now is black, and it matches a lot of my shoes. It's sort of accidentally matchy, and often I appreciate the effect -- I like a dose of black in my outfits and shoes + bag is often just the right amount, while allowing me to wear brighter/lighter colors in my actual clothes. Very useful in summer, for me. But somewhat dull in the winter when I can easily end up in an all-dark outfit especially when outside. So backwards, I know -- loving my black bag in summer and wanting a bright bag for winter. That said, if I do add a light/bright bag, I won't go to any great lengths to create a shoe or accessory complement for it, as light/bright shoes aren't practical for my winter. I'm thinking a bright red bag might make the most sense, as it would coordinate with my mostly black and burgundy winter footwear and I do have quite a few red and burgundy winter accessories. I like the idea of tan/cognac bags, too, but have a feeling it would lead me down the rabbit hole of adding tan and brown boots to go with it (also, tan bags almost always have gold or brass hardware, and I don't want warm metals).

So I'm curious -- when you add footwear, bags, accessories, do you have a strategy for matching or creating complements? Are you strict about the colours you add, or is your approach more spontaneous/hodgepodge?