I also feel like the bag needs to go with the outfit, but that may or may not mean that it ends up matching the shoes. I am not adverse to shoes and bag in the same color if it makes sense in the overall context of the outfit, but I don't go out of my way to make them match.

However, if my shoes are a neutral, like cognac, that is not apparent anywhere else in my outfit, I might feel inclined to choose a belt or bag in a similar tone or shade.

Well now, this is a good question. It's traditional to consider handbag and shoes together. And I realise I do this - I consider visual weight, consistency of style, and tones, and against my outerwear. But I do this only to a limited extent. My RATENESS leaves a lot of room...

I love bags and have them in a myriad of colours and shapes! I never worry about matching my shoes, but I do worry about matching my outfit. My current favs are a deep purple MK satchel and a merlot tote. When I wear my red pea coat, I carry the merlot; when I wear my black trench, I carry the purple bag. I can wear either bag with my grey puffer.

Hmm . . . if you are bag-loyal, it makes sense to think about shoes, right? Because if bag and shoes work together you will look pulled together regardless.

This is a new concept for me. In the past I've been casual about bags, picking one because I liked it enough and sticking with it for a long time. But now that I'm rebuilding my wardrobe I'm thinking about the bag/shoe thing and want everything to work together. No orphans. It's exciting actually, thinking about bag/shoe pairings for the first time. I feel like a whole new door has opened.

I NEVER think about shoes or bag or coat going together. I probably should at times, because today I've got two plaids and a stripe going on. I've never understood how a bag "goes" with an outfit, other than the most basic concepts like a clutch with a dressy look.

On the other hand, I tend to stick with black shoes and bag in general so maybe that's why it's not a struggle.