After scouring the internet for a pair of FLAT and TALL boots (contrary to the normal: spiked tall boots) I tried on these at Macy's to find my size before ordering them online. I'd say they fit true to size, maybe purchase a half to a whole size bigger depending on your calf muscle size and whether or not you want to wear thick socks/tuck in your jeans-a size too small and I can see how the leather detailing dividing the shin and knee area could possibly rub wrong, so if you are concerned at all, just order a slightly larger size. These are very comfortable to walk in!