Searching for the right pair of boots can be a bit of a challenge per season, but if you know what shape is best essential to your lifestyle and wardrobe -- then you're off to a great start. When you think about it, buying a new necessary pair of boots is similar to the anticipation of a one-night-stand. Let me explain. In the moment you think you need them and have to go home with them because if you don't -- then, well you'll regret it. Oh, and let's not forget the walk of shame once it's all set and done. In this case in regard to shopping, the buyers remorse sets in and your bank account hates you for taking the sartorial plunge. See what I did there? It happens to us more than we'd like to admit, ladies. Before you even think about feeling ashamed, the Chicest Degree has curated the ankle bootie edit featuring the most wanted hardware-adorned styles of the season for your shopping pleasure.