The Best Hats for Different Head Types
Credit: Marcello Mastroianni on the set of Federico Fellini's '8 1/2', 1963. - Getty Images

"It's honestly nothing new," Ben Goorin, founder of the expanding Goorin Bros. hat empire, says of the ubiquity of trademark caps on leading men like Bryan Cranston and Jon Hamm. "It's always been the most confident cats that are willing to stand out and make a mark of distinction." What is new according to the fourth-generation milliner, is normal guys' willingness to try on new toppers. Still, the hat-maker admits that finding a cap that actually looks good can be a bit tricky.

"The right hat creates symmetry on your face and brings balance to your head shape," he explains. "A shorter one is going to look good on somebody with a narrow face and just the opposite – a wider brim is going to look better on people with fuller, more rounded faces." With the crown (the height of the hat) the idea is to accentuate your positive features without creating an extreme look. A broader brim cuts the vertical lines of a long face and a taped hat un-squeezes squat features.

But even the perfect hat won't look good if it isn't worn correctly. That's why Goorin, who is about to open his first location in Las Vegas, advises customers at his 28 stores to tug on their brims. "Tilt your hat instead of putting it on straight," he orders. "That offsets the continuous line in your face and really makes a big difference."

Here's his millinery prescription for the major face shapes.

Square Face
"If you have more of a square-shaped face, you want hats that have rounded edges and curves to offset the straight edges," says Goorin. "That translates into a flip-up fedora, which literally flips-up in the font and the back and creates a rounded look to offset the sharp edges of a square face."

Round Face
"A hat with a medium-height crown and a brim that's medium to long like our heritage felt Doctor Fedora compliments a round face nicely," he says. "Another important thing to consider is a narrow band. That gives the illusion of an even higher crown and makes the hat appear like it has more length. 

Short Face
"You want to create the illusion that you're stretching your face, so you want to avoid a high crown in favor of one that's tapered," advises Goorin. "We recommend the North, a shorter crown fedora, or the mining, which is really soft and looks great on a short face."

Long Face
"You want to find a hat that will help shorten the appearance of a long face," says Goorin. "But if the brim is too narrow, it's going to overemphasize your long lines. So go for something with a moderately lengthy one, like a pork pie or our flat welder cap. And tilt it! You don't want to keep extending a long face into your hat." [Hats from $28; goorin.com