Labor Day is always a day of mixed feelings for me. Summer is technically over, the temperature has yet to drop, leading to the ultimate transitional season, Fall, which in my humble opinion, is the most fun season to dress. As a Chicagoan, I always hesitate to whip out my tall boots, knowing that my tired feet will not see daylight after being in those things for at least 5 months. Enter: the bootie. You can wear with bare legs, jeans, or even pair them with a maxi to get some extra mileage out of it. Aside from the extra ankle support that makes booties ultra comfy, their shorter stature let’s you have a bit more fun, with colors and embellishments that would look a little too much on a higher boot. I found you, Miss New Bootie!