[$105, Ben Sherman]
Not everyone can pull off the retro sunglasses look. In fact, few can do it successfully, and most people just end up looking pretty douchey when they try. But those lucky ones who can pull it off with panache, look so cool in this look that you can almost forgive them if they wear the sunglasses at night or indoors. If you can so without the tortoise frames and the leather case this Ben Sherman pair comes with, there's a more afforable option that saves you nearly 75%:
[$28, UrbanOutfitters]