20. The Open-Toed Bootie — The shift from wearing booties every day to not wearing them at all when the weather breaks can be hard to handle. But, given there are so many sophisticated open-toed booties out there to choose from, your transition can be virtually seamless. We've already started wearing ours with long dresses, slouchy trousers, jeans, you name it. Now, all you have to do is choose a stiletto or a chunkier heel…we like 'em both.  

3.1 Phillip Lim Akita Lace-Up Booties, $850, available at Ssense; True Religion Shoes, $69, available at DJPremium.