However serious the business of fashion is, the wearing of it is even more so. Our mode of dress is a kind of social discourse—something women understand instinctively. We know that the right handbag dangling off an appealing arm or slung over an insouciant shoulder is a kind of "plumage" that sends messages about our moods and reflects who we are. So when we choose an unusual vintage design, we make a bold statement about our individuality and appreciation for the foundations of modern fashion.

One subset of vintage handbags makes a particularly lively statement: the "Wit and Whimsy" bags. These lighthearted designs have a contagious sense of humor about them. They invite a smile, demand questions and command high prices.

Perhaps the most iconic of these is the Moschino Dripping Chocolate bolide, a delightful bag and feast for the eyes. Just leave this little treasure on the coffee table next to the cupcakes, and watch the conversation turn to laughter. Then there's Nettie Rosenstein's exquisite branch coral bag from the late 1940s. Beautifully made, each branch is sewn on by hand, resulting in a rare and luxurious density of real coral—which of course cannot be used today. The vivid color of this unique, inspired bag evokes images of white sands and turquoise seas.

There's nothing like a whimsical vintage handbag to express your lighter side. And with these lighthearted, subtly seductive pieces, the statement you'll make is undeniably fun.