The Wide
Brimmed Hat

Rosin, $45

There's sensing a trend is emerging and then there's hearing it straight from the horse's mouth so to speak. When it comes to discerning what's resonating with real people—instead of simply reporting on fashion industry trends—there may be no one better than Bill Cunningham. The New York Times photographer has been documenting style on the street for more than five decades and recently he declared the wide brimmed hat the accessory of the moment. "Number one is the felt fedora or the wide brimmed flat hat," says Cunningham who saw multiple hats on stylish dudes attending the recent Men's Fashion Week. "They're bringing a fresh interpretation of the classic suit, shirt, tie ... for a new generation."

It's definitely a new twist on a timeless accessory. These classic hat styles have been around for a while, but now are finding new ways to liven up your everyday outfits. Make no mistake: a hat can change the look of your face (and overall style) more than any other garment you could wear. Which may be why some men struggle with trying one. But these easygoing, wide brimmed styles add instant swagger to whatever you're wearing. And when the sun really starts shining, these have the added benefit of keeping the rays off your neck and out of your eyes.