Cole Haan Cranston Chukka

via Colehaan.com

A classic wardrobe staple from fall to spring, the chukka boot is a more formally-styled casual shoe that is great for work in a casual office setting, and an awesome shoe to wear going out. Chukkas provide a clean line and some character that every girl will notice, because while you're looking at her neck line, she's checking out your shoe game. Their leather construction provides some forgiveness when you inevitably spill something on them, and the harder sole gives you the support and durability you need for them to stay comfortable and last. These chukkas are also water resistant so you don't have to worry if you're stepping out in the rain. 

Available on Colehaan.com for $280