I am working on completing my complements, and the first "bigger ticket" item I am tackling is a brown bag.
I have quite a few booties/boots in different tones of brown (below in Finds), and am considering adding a pair of chunky loafers/oxfords (in dark cool brown patent), too, but haven't quite decided yet. The only bag in this color family I have is an old BR cognac (next to the beret) I am lukewarm about, so would like a new brown bag.
Regarding browns, since my coloring is cool toned, I wear dark chocolate browns (like the beret and the first, DP booties) next to my face and all sorts of browns away from the face. My favorite "non-flattering" brown is rust (like the MF booties). I tend to wear browns most often with navy/shades of blue.
I am struggling with choosing a bag, as with the range of the brown toned booties it is not possible to match them all. I am trying to figure out which color choice will go the best with all the shoe options. I'd like a medium-to-small leather bag that can be worn cross-body style. Ideally, the hardware should be silver/gunmetal, but since that is very hard to find with brown bags I can settle for gold as long as there isn't too much of it. I know that I do not want a leopard or something with lots of black in it (a little is fine).

I have added a couple of possibilities. I am open to other suggestions as well, both conceptual and literal.
1) Go for my best brown, dark chocolate (like the Botkier crossbody)
2) Go for my favorite non-flattering brown, rust (like the Madewell tote)
3) Colorblock (also Madewell, camera bag)
4) Snakeskin in tones of brown (Botkier hobo bag)
5) A slightly different approach, tan (to match my hair) with a snakeskin strap (Marc Jacobs)

ETA: the plot thickens! Apparently Botkier crossbody does come in the same dark chocolate/cognac/cream color block. Decisions, decisions...