My 2 for $250 selection: brown shaker heights and brown distressed pine rivers. Both shoes were never on my radar at MSRP but with the sale, I thought they would be good buys. My wife loves the shakers, thinks I should get more mixed media shoes. The pine river on the other hand isn't her favorite, the buckles are killing her.
My opinion on the shakers are that they are great, very soft leather and awesome design. The pine rivers are a stretch out of my comfort zone but I feel they will work great casually.