A couple of things i like about the 269. I kind of like the thinner black line that it gives you through the soul, just for aesthetics. And I like the way it narrows underneath the arch. The standard half sole makes the boot seem a little too skinny there for my taste. And as James says, it feels pretty good on the pavement and has decent grip. Definitely worth considering. For some reason I feel like you don't see it often on the standard dress brown SDs.