Head Games

I truly miss the days when it was commonplace for men to be clad in fine headwear. There was a time when before a well dressed gentleman met the light of day, he’d place a smart fedora or playful porkpie atop his head. Everyone wore hats, even children. However, like so many other accessories, what was once a necessity became a novelty and languished in relative obscurity. Kept alive by artists, musicians and eccentrics, lids worn by laymen were a rarity. Well it seems that this ageless tradition is making a comeback after years in exile and I couldn’t be more pleased. The men in my family never betrayed their brims, wearing them with a sense of pride. Credit artists like Andre 3000 from the rap group Outkast and actors Johnny Depp, Brad Pitt, in addition to R. Kelley, Kidd Rock and others for resurgence in the mainstream.

In the January 2008, GQ Magazine published an excellent feature on hats, asserting that, “Yes, hats are back.” The piece then went on to ask this question of its readers, “Do you know a fedora from a porkpie?” Chances are most didn’t and still don’t. In light of this men’s accessory making a resplendent comeback, I pose that very same query to you now. For years it seemed as if there were only three types of hats men would still wear. There was the ball cap, a true American staple and worn by men and women of all ages. The ball cap is so popular because of its relationship with sports and the service industry. It’s a way to show team spirit and to advertise your company or business. In recent years, couture brands like Von Dutch and Ed Hardy, in addition to iconic marks Gucci, Louis Vitton, Polo and others have literally thrown their hats in the ring, jacking up the price and elevating the cache of this simple staple.

Then there’s the skully, skull or watch cap. This style is more of a necessity than accessory, although much like its cousin the ball cap, it too has been invited to the ball. The skull cap is worn to keep us warm. Anyone who lives in Chicago and has experienced the Hawk, you know you need a hat to keep the chill at bay. Those who brave the elements here, without one, are either too vein, in denial or just plain bananas. Watch caps are standard issue for most troops stationed on cold weather campaigns. More and more I see people wearing skullys in warmer climates. I’m really not sure what the point of that is, but hey to each is own. Thirdly there’s the driving cap, which in some configurations is also known as a newsboy. The difference is that the newsboy cap has a larger diameter. The driving cap is very versatile. It can be worn traditionally, or tipped to either side or Samuel L. Jackson style—flipped to the back. That’s the way I like to wear mine. Depending on the fabric, driving caps are an all season option; wool or corduroy during autumn and winter and cotton, silk or other lighter fabrics for spring and summer.

Hip Hop bohemian and Chicago native Common rocks a newsboy like no one else. Other than a skullcap, the newsboy is part of his persona. Common doesn’t just wear his hats; he tailors a lyrical contour, making it an extension of his velvety flow. Starting by cocking it slightly to one side, he adds a modest tilt then bends the brim downward all to create a splendid upward curl with the crown. It’s a look that’s copied by other entertainers and some manage to pull it off, but most don’t have the swagger needed to give it that thump of urban authenticity. The fishing or bucket hat gets an honorable mention but it’s another one that can make you look silly if worn under erroneous circumstances.

That little black hat you see perched atop Joe Jackson‘s bean is called a Trillby. The Trillby is basically a petite version of a fedora with a stingy brim. This style gained popularity over the past few years thanks to boy banders like Justin Timberlake and rockers like Pete Doherty. It’s the training wheel of hats, a great jump off for hipsters or older cats new to the game. More recently the trillby has become a female favorite as well. Next is the fedora. The fedora is a timeless classic. When you think fedora, think Bill Cosby, Steve Harvey, Frank Sinatra, your pops or granddaddy. This is the Caddy of caps. It goes great with suits, sweaters and is a must have if you’re serious about haberdashery. The fedora has a wide brim, a sharp crease down the center of the crown and dimples on each side. You can find them in felt, straw and even leather. When worn properly, the fedora will set off any well suited ensemble. Similarly there’s the panama. Panama hats are akin to lightweight fedoras but are usually woven from toquilla straw originating from iraca plants. Some panamas will have rounded crowns and may or may not have the customary pinches found on fedoras.

Following the fedora is the porkpie. If you remember Ron from the ‘Cosby Show’ spin-off, ‘A Different World’, then you’ll know the porkpie. Ron nearly always wore one and he looked good in it. The porkpie has a crown that resembles a round cake or deep dish pie pan and a flat brim that’s often turned up on all sides. It was a favorite of the musicians in the Spike Lee Joint, ‘Mo Betta Blues’ and remains a style largely popularized by jazz artists, clean cut preppies and oddly enough according to GQ, Jamaican “rude-boy rebels”. Ire mon.

When you go to the state fair, carnivals or watch footage of old political conventions you’ll see a hat that looks a lot like the porkpie but it’s actually called a boater. The boater is fashioned from thick baked straw with a flat firm brim and tri-color band around the crown. It was once a favorite of barbershop quartets and turn of the century sportsmen engaging in polite games of croquet or horseshoes, the boater remains more of a novelty than a truly viable fashion alternative. Andre 3000 manages to pull this off, but he’s an enigma. I’d forgo the boater if you want to be taken seriously and not look like some relic from the dust bowl.

Finally, with the passing of Michael Jackson, we’ve been seeing a lot more of his family on the news and in print. Mike loved hats; he wore them all the time, not only as extensions of his unique style, but they bore a functional purpose as well. He wore them to protect his face and scalp from the sun. We’ve seen his father balancing a trillby on his head and now it seems that Tito has gotten into the act by sporting a bowler. He looks even sillier in his bowler than his father does in that tiny trillby. Bowlers have a bulbous crown, turned up brim and almost always come in black felt. This is a style that should be left to those across the pond in jolly old England. Tito looks like he should be feeding nuts to a monkey cranking an organ grinder. Clearly Michael’s fashion sense didn’t rub off on his pops or older brother. Joe should stick to a fedora, possibly a newsboy and Tito could actually play the porkpie, fedora, newsboy or skully quite well. Take my advice guys, make that change.

Whether you use them when you’re dressing up or dressing down, try incorporating hats into your wardrobe. It’s defiantly an upgrade to your game and can take you from spectator to player once you’ve found the style that’s right for you. Remember, in the words of Ben Goorin, President of Goorin Brothers in San Francisco, “A hat allows a man to make a statement without saying a word.”

Choose wisely my friends.

Now Let It Breathe.