Men’s Hats

Symmetry plays a large role in what humans find attractive: The more symmetrical the face, the more appealing it seems to others. While women have the option of choosing a hairstyle that covers a protruding forehead or one that balances a crooked smile, men have embraced hats as their own form of a distraction from less than perfect features. Whether you’re going from dull to debonair in Kangol’s “Tropic Player” in white, $45, channeling a 20th Century golfer under Bailey’s linen ivy cap, $40, or sporting the equally as vintage Bailey’s slate cap, $48, you’re sure to be ahead of the game. For legendary style icon Frank Sinatra, the hat that seemed to always suit his mood and top his outfit was the fedora. These days, the Rat Pack swagger of the 60s meets 21st century flair with Bailey’s “Mannes” fedora in black/tan, $49; the “Panama” by Makins, $125; and Bailey’s “Monroe” in ivory/black, $48. Or try Bailey’s Salem” hat, $50, which features a striped band above the brim that adds a stroke of color to the classic style without being too brash. While these featured styles may make the man, there are rules when it comes to hat etiquette: Never wear your hat during a meal, but always remember to wear it with pride—if it looks like a costume, no one will take you seriously.