This is my dream capsule: not the specific pieces--too dressy for my needs--but the discipline of it!
Like Alaskagirl said, print out each thing on a card and play pretend paper dolls with them!
Alternately, I would do an enourmous spreadsheet/table with six columns and as many rows as necessary. Column 1: bottoms. Column 2: tops that go wth each bottom. column 3: all the jackets that will go with each top and bottom combo. Column 4: each pair of shoes that go with each bottom plus top plus jacket combo. Do the same for (5) bags and (6) scarves.
There are 7x20x5 options (give or take) before we get to accessories. (#9, 10, 13 and 14 can be layered over the other tops, too, and that's where things go a bit snakey mathwise on me.)
But just for fun,'cause this is fun, How about the leopard blouse (#8) with the cream pullover (#13) and the black and tan pants (#32). Accessorize with the leopard shoes--or if you don't want to be that atchy matchy, try the bbrown boots #14 with the brown bag #3.
Another one:
Black and taupe blouse #6 with the black and tan trousers #32 and use the taupe pullover (#14) to keep them from fighting. For the accessories, though, I have to leave that up to you depending on how you'd want to take it from there.
Now,both of these suggestions are going off of your descriptions and what I can see on my screen: reality may be completely different! I'm just trying to be as "out of the box" as I can in order to help stimulate your creative juices.
Thanks for posting this Carter. It is fantastic.