Johnny Depp wearing a cool hat

On men, baseball caps blow, but the fedora kicks it. That’s all you need to know.

What is it about men’s hats that inspires such division and derision? In the October 2010 issue of Esquire Magazine, the magazine’s fashion director, Nick Sullivan, answers a question posed by a reader: “What, what, what is your problem with hats?”

In keeping with his typical hater attitude towards hats (“hatter hater”?), Sullivan replies “…in the 21st century, a man cannot wear a brimmed hat like a fedora without making some kind of statement. A man does not wear a fedora now to fit in, as he did in our grandfathers’ times; he wears it to stand out and to say, ‘Hey, look at me, I’ve got a hat on.’”

Now that’s a moronic statement, IMHO. Notably he singles out ‘brimmed hats’ such as fedoras, so that must mean he accepts beanies, toques and skullcaps as a fashion statement. Why must men be without stylish hats even though women can wear them? As a man who wears hats most of the time, at least when I’m not showering, swimming or having sex (and even then!), I feel obliged to tilt my hat brim to a pugilistic angle and step into this fashion brawl.

Back in the day, men started wearing hats to cover their heads in the sunshine or protect their skulls in battle, but hats have a transformative quality, which is why the expression “I’m wearing different hats” was coined to mean that someone is playing different roles. When you don a hat, you top yourself with a brand new image and persona. Kings could have worn a badass breastplate to show their status, but there’s nothing like a bejeweled crown to say, “I am the shit. And you’re not.”

Hugh Jackman Fedora

We’ve all seen men wearing hats that do not suit them, hats that inspire people to mutter pejoratives under the breath as they pass a hat poseur on the street. And there’s the Tilley hat, a classic Old Dude hat, at least where I live. Sometimes I think Tilley must do deep discounting for customers 65 and older.

The 90s were a dismal time for the state of men’s millinery. Baseball caps adorned the noggins of every young dude in the world. In every conceivable color and fabric. Sick of your cap style? There were endless variations available, all of them abysmal, including the trucker hat with its plastic mesh air conditioning system…a hair net, not a hat.

Man in an uncool baseball cap

Some hats, though, mark a man as a gentleman, a man of style and confidence, not necessarily a metrosexual but someone who is comfortable accenting his personal style with a hat that suits his wardrobe. You wouldn’t wear a bowler hat with GORE-TEX® outerwear (or maybe some people would), and neither would you wear a pith helmet with your Armani suit. The hat has to match the man, the wardrobe and the occasion.

To achieve that perfect alchemy of hat and garment, you have to try it on. In front of a mirror. Does it look too small on your head? Pass. Is its brim so wide that you look aerodynamic? Pass. Then what kind of hat should you choose? The fedora in all its varieties is one option to consider. In the summer you can wear a Panama hat, one of the world’s most popular fedoras, and in the fall and winter, a dark, felt Stetson fedora. Fedoras offer men a touch of hauteur, but not too much that you look like a snob or an eccentric.

Van Gogh In A Cool Hat

And it’s not just the hat itself that makes an impression; it’s how you wear the hat. Tip your fedora forward a bit, and you look like you are on a mission: don’t stand in my way! Cocked to the side a bit, but still forward, you’ve captured that Frank Sinatra or Mad Men rakishness—a bit corny, yes, but if you can pull it off with irony and a sense of humor, also very sexy. Or tip it back on your head so the front of the brim angles upward and you appear open, personable and even approachable. All with the same hat.

Regardless of what Sullivan believes, men don’t always wear hats out of “Look at me” vanity any more than they wear a suit, tie or shoes to make that same kind of statement. A hat is a time-honored way to bring your personality to the surface when you want to express who you are or convey your attitude in a certain setting or at an event. I can tip my hat to that.

To keep up on hats and who’s wearing them, visit the Hat Sighs blog.