Chris, your preferences sound similar to mine and you have worked them out a lot quicker than I did! (Hmm, I am sensing a pattern here. You're a quick study and I am a slow learner!)
Like you, I prefer to carry a bag on my shoulder (or crossbody) vs. on my arm. But I also prefer a structured satchel style. Soft bags drive me crazy. I often like how they look, but in practice they annoy me beyond all imagining. Also, I don't care for a lot of hardware. So it's always a bit tricky to find the bags I want.
When I joined YLF I had, literally, one bag, and it wasn't serving me well. I have since built up a collection, but not very systematically. I have discovered that I like having more variety in summer than winter. And I like having at least 4 main types of bag.
- Tote -- I need this and use it most because I walk everywhere and carry my computer with me most of the time.
- A somewhat smaller structured bag (e.g. satchel or shopper) for everyday when I am not carrying computer.
- A dressier, smaller bag, such as a clutch or cross body.
- A fashion backpack. I use this as a substitute tote and also a shopping bag, and carry my gym stuff in it as well.
So this is similar to Angie's 3 bag complement.
I switch it up by season, though. Except for the fashion backpack which is navy and works in all seasons. It's also vegan so I can take it out in the rain -- a useful feature in my life.
So my winter tote (currently) is a sort of textured charcoal leather...but it's a bit heavy and unwieldy so I haven't been using it much. In addition I have a dark grey Le Pliage which I used constantly last year but which does not have enough structure to please me as a regular use bag and is overall too casual with its brown handles.
Summer tote is two tone black and bone. Also lacks firm structure unless it is full and I have since learned I don't care for that. Ah well.
Summer structured bag is a bright cobalt.
Winter.... I don't really have one. (Wardrobe hole).
Summer clutch/ crossbody: I have hot pink, black and white spotted, and dressy gold, silver, black. I also have a cognac crossbody and a black and white colourblock small shoulder bag -- a bit worn out.
Winter clutch: black and white spotted, black with leopard print clutch. Also, cognac crossbody and vintage Coach burgundy crossbody.