Well, no, I am not the whiskey-smuggling, illegal-activity kind of bootlegger, but for the number of times I wear boots when the weather cools, I feel that I must redefine the term! (Fashion) Bootlegger: noun. 1 a: someone who wears boots to ward off cold feet and legs. verb. Bootlegging 1 a: the art of wearing boots as a replacement for stockings and and sock wear.
The truth is that when the weather cools you need a go-to type of shoe; something that does more than add height to your look but actually redefines how you warm your legs. Boots are your answer. You will need to remember the following when purchasing a pair (or two, or three!) of winter boots: find a color that is versatile and will go will most things (black is always a good idea), a little heel (like a wedge) is a perfect compliment to both pants and skirts and dresses, and a weatherproof boot will be your new best friend if you get caught in drizzle or rain or snow. And remember to make sure your boots aren’t too tight-fitting – you want to have enough room to accommodate heavier socks and tights. When you do, you will find yourself wearing boots dressed up and dressed down, always and in all ways. Become a bootlegger, like me, and give this naughty word a whole new meaning!
Photos by Kendra Olson