There are four boots every women should have in their closet: chelsea boots, rain boots, over the knee boots, and a heeled ankle boots. I consider the heeled ankle boots I purchased at J.Crew a few years ago to be one of my best investments. They get a steady rotation each year, pairing well with almost any outfit, but my go-to combination is most always similar to this. They dress up an outfit if the weather does not permit heels, but can also feel casual if worn with jeans. Plus, I can wear mine all day with comfort. If you're in the market for a pair, see below for a few of my favorite picks.