As for keeping 1 pair in each color, for me, the walnut and dark brown are so different that I consider them different colors.
I recommend staying away from Cole Haan. You will likely end up replacing them in the future with a better quality shoe, at which point you will have wasted your money on the Cole Haans.
Is keeping all 4 pairs if shoes an option?
Hmmm, I'm still waiting on my Fifth Avenues to come in. But when I saw them in store, I absolutely loved them. I would much rather not spend that much right away on 4 pairs of shoes, but if I can't decide, I may have to just keep them all.
I would suggest throwing saved money into a pair of Daltons or Bayfields or whatever boots AE introduces for the fall. I picked up a pair of nice goodyear-welted semi-dress boots a few years ago and they've become one of my most-worn shoes. You really won't regret it. Boots are like shell -- you get one pair and suddenly you really want more.
Seconded. I only purchased black shell Leeds because they showed up new on eBay for a steal. I would've paid twice as much for burgundy shell. Still might, if the two pair at shoebank are still around a month or two from now...
I've never considered boots haha. I can't really picture myself wearing a pair of boots to work, not that there's anything wrong with it. But generally, I don't like mid or high sneakers. I would assume that would be the same for dress shoes?