Subjectively speaking, spring represents straw hats. But what to do if the weather is still a bit on the chilly side? Do what the Victorians did: wear dark colored straws, trimmed in velvet. In the Roaring Twenties, they wore light colored felts; you can use this as your transitional hat of choice.
Think color, use felt, lean on velvet trims, and you have a perfect spring wardrobe of hats. Of course, in New York City, the first think we grab in the morning is a black fedora. If this is the hat carrousel you're caught on, add a feather to the fedora . The whimsy will awaken your inner Spring, and get you in the mood for other possibilities.
Kentucky Derby, here we come!