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Top 10 Hats for Guys and What They Say About You

by DannyGallagher   January 18, 2011 at 10:00AM  |  Views: 10,220

5. The Panama

Source: Michael Brinson/Iconica/Getty Images

This native head hanger of South American dates back to the 16th Century when Spanish conquistadors discovered it in what we now know as Ecuador. The straw hats were adopted by the Spaniards and soon spread to just about every corner of history and the globe from the 1848 Gold Rush to the construction of the Panama Canal. It was made for dredging through heavy tropical lands in search of lost Incan treasure or grabbing a quick power nap on the beach to work off the seven Mojitos your body can’t process. Plus, you had to wear it because the gift shop didn’t carry sombreros, no matter how many times you screamed for one.

What Does This Hat Say About Me When I Wear It?

“Which way to the Fiesta deck?”

“I actually have no idea where the country of Panama is.”

“I so think I could kick Ernest Hemmingway’s ass.”

4. The Homburg

Source: Dorling Kindersley/Getty Images

Accompanied with a medium brim and the occasional feather, this hat (I ran out of clever hat synonyms a couple of sentences back) came from Germany in the late 19th century but eventually emigrated to America and became a regular fixture among gangsters, even earning the infamous nickname as “The Godfather Hat.” Ironically, Marlon Brando’s status in life as a huge tub of gelatinous lard would earn super-sized stretch wasteband pants the unfortunate nickname of “The Godfather’s Pants” although I’m sure that had more to do with Godfather’s Pizza than The Godfather movies.

What Does This Hat Say About Me When I Wear It?

“Where’s my gun?”

“How hard is it for me to remember the words, ‘May your first child be a masculine child’?”

“Nyah, you’ll never take me alive, copper. Dead? Quite probably. Wounded? Maybe 5 to 1. Winded? Sure, I’m a big tub of lard, see? Nyah, nyah.”

3. The Porkpie

Source: Michael Turek/Photodisc/Getty Images

The British gave this short and snappy hat its start, but its popularity spread and soon everyone from jazz musicians to football coaches took to wearing it on the job. It’s a good, straightforward, “let’s get down to business” kind of hat, the kind that makes people get out of your way because you’ve obviously got important music to write or a hard-as-nails case to solve. It’s a hat that screams importance and attention and God help the man who gets in your way.

What Does This Hat Say About Me When I Wear It?

“She walked into my office like a sweaty stack of pancakes. I took one more pull of Jack Daniels and loaded my gun that I had hidden under the stack of unpaid bills on my desk. The smoke hung in the air like a broccoli fart in a sauna. This wasn’t gonna be an easy dame, I mean case, to crack open.”

“Help! I’ve fallen through a worm hole and need to get back to 1945!”

2. The Stetson

Source: Creative Crop/Digital Vision/Getty Images

This iconic piece of clothing has carved an important place in the history of the old west. Cowboys may have worn to keep the blazing sun out of their eyes during long cattle drives but it’s become a necessary and important tool in the development of the modern Southern tool. The only reason anyone today would wear one is because rodeos don’t allow helmets and it sort of makes you look like you could kick someone’s ass, at least more than a fez ever could.

What Does This Hat Say About Me When I Wear It?

“I think I’m a cowboy, even though I’ve never seen a cow in my life.”

“I showered in Stetson cologne this morning, too.”

“I’m not gonna hit ya, the hell I’m not, assuming there aren’t any cops around.”

1. The Fedora

Source: Sam Bloomberg-Rissman/Flickr/Getty Images

You can’t go wrong with this classic among classics. It’s become so engrained in the modern suit that all the greats from Humphrey to Indiana wore one and people still wear them because they still think they can be like them. Even though the truth is the closest they could come to smuggling the dame they once loved out of a military-occupied country is that time they got out of dinner with her the in-laws by faking food poisoning.

What Does This Hat Say About Me When I Wear It?

Indiana Jones hasn’t stopped playing in my head since I was five.”

“I believe that great advertising will make the world a better place.”

“I’d rather be chain smoking.”



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