For me, a pair of dark wash jeans would be the canvas to start with.
Thinking about this some more...
I might next consider a color theme - perhaps pick two or three colors that go together. Maybe I'd start with a patterned top that I already have in my closet, for the inspiration.
For example, maybe I'd start with this top:
http://teamsugar.com/look/1557169
Color theme: white, turquoise, navy. I'm choosing this just for inspiration.
This top goes with a white jacket, or a turquoise caridgan. So those would be my two layering pieces, and there's two outfits right there.
That leaves me with just two tops left! Ack!
This black & white striped top would go with both the white jacket and the turquoise cardi - for two more outfits:
http://teamsugar.com/look/1548529
Hmm... maybe I would swap out the third shirt for a pair of white pants, which would go with both those two tops, and the blue cardi.
Shoes: I would want a jolt of color for interest. Yellow!
Okay but that may seem too similar day ofter day. Hmm.
Hmm... dresses might work best here!
How about:
2 versatile dresses
1 jacket
2 cardis
1 pair shoes
1 bag
3 items of jewelry
.... yep, dresses would get you more mileage! If both dresses went with the jacket and the 2 cardis, that would give you 6 days' worth of outfits...