7. The Quirky Sneaker — Admit it: Sneakers are appealing, even if you're not the casual type. And this fall, you don't have to swap good style for a great, comfy pair given all the playful options out there (many of them with a nice little hidden lift, too).  

Adidas x Opening Ceremony Cycling Wedge, $235, available at Barneys; Kenzo x Vans Sneakers, $125, pre-order at Opening Ceremony.