Im surprised reading some of these reviews. Ive had mine for over 2 years and they still look awesome and feel great. There is no "heel squishing" and the leather is very thick...where I too thought it might cause blisters (but didnt) to break in.  These are one of the finest pairs of chukka style shoes I own. I would highly recommend them. I work retail so...when I wear these, they get MILES of use on any given day....theyve been great!