Hamilton Straw Hat

When California-based designer Janessa Leone creates a new style for her namesake millinery brand, she doesn’t pay heed to trends. Far more inspired by silhouettes of eras past, Janessa Leone hats are all about reconnecting to a time when toppers were not only worn more frequently, but made to last. And while craftsmanship is the brand’s first priority—each hat is completely handmade—aesthetic ranks a close second. Since the label’s 2012 launch, Janessa Leone felt fedoras, Panama beach hats, and floppy wide-brims have been go-to pieces for making any outfit instantly cooler.