Anyone who's ever shopped knows that buying a good handbag is no cheap endeavor. And when you move into the territory of deciding between a classic bag or a trendy one? Good luck. That iconic Mansur Gavriel bucket bag may seem like a better choice than a $300 raffia crossbody, but let's not forget that the $600 leather bucket bag was once nothing more than a "trend" itself. It's smart to be wary when making the jump towards a pricey bag when you're not quite sure what a bag's longevity looks like. Which is why we often like to test the waters before we invest.