With apologies for the crappy lighting, here's a pic of C&J dark brown and C&J chestnut side by side paired with navy trousers. I like the chestnut color better, and really like the way that this pair has aged - as DonRaphael indicated the he was planning on doing with his Westbournes, these have seen some black polish, but they're definitely more "noticable" when you wear them.
I agree with you that my chestnut shoes also ages better than my brown calf in term of color. Great looking shoes btw, both the Lowndes and Selbourne.
The fact that the "thing" generating the funny feeling is depicted in the medallion might have something to do with it..