With our shorts officially retired for the rest of the year, we recognized a small problem: all of our boots we getting a little long in the tooth. After looking around, we're pretty hot on these Cole Haan Dylan Buckle Boots ($225). Made from distressed leather with contrast stitching and sporting a mid-calf fit, these boots are made to look as good as they feel, and are the perfect thing to keep your toes warm and safe on a cold night out.