http://www.zappos.com/product/.....ap_pdp_sub

I think this is the new version of what I will actually buy. I'm going to buy from my local Macys and the colors are slightly different and the price isn't the same either, though close. This will be my first "investment" bag.

I've ruled out black because I want it to be a year-round satchel-type bag, and I don't grab black bags in the summer.

I'm torn between a cognac-ish brown (like Lyn's) and gray. If I'm wearing cognac boots, will it look silly? My brain can't come to terms with the "shoes must not match shoes" thing I've read a few places. I don't aim for them to match, but if they do sometimes, is that ok?

Which would you choose? Cognac or gray? Note: the gray I would buy is a darker gray than this link/pic shows.