We can’t always explain why we’re drawn to certain pieces. Sometimes the clothes we just can’t stop thinking about aren’t the obvious investment buys. But then again, we’ve always said that classic shouldn’t mean boring. So when we’re trying to decide whether to buy something that doesn’t feel as safe as, say, a white shirt or LBD, we consider how much we really love it. Because that’s a good indication of how much we’ll wear it. After all, personal style isn’t necessarily defined by the bones of your wardrobe as much as it is by those pieces that are a little outside the box.