I'm a true size 8 medium width. My calf is 16 1/2 inches. These boots fit like a dream for me and look just as nice. They even fit my thicker knee/ thigh area with no tightness or discomfort. Haven't had any issues with the quality so far, but I don't wear them more than 1x per week. I do recommend that you spray a coating of Totes leather protector or ScotchBrite waterproofing to keep the feet dry. I did this and then I wore them on a heavy rain night, stepping in ankle deep puddles with no issues. Seal your boots, folks!