Daniel Marsula, Post-Gazette Click illustration for for larger image.

Oh, you should talk about underpants! ... Matching underwear to T-shirts in sets for boys is the cutest thing ever!"

There it was -- I found it. On the second floor of the American Apparel store in Shadyside, staring at a tiny pair of pink men's briefs and a matching pink T-shirt, a kindly store manager showed it to me -- my cool heart of darkness.

My superiors at the Post-Gazette asked me to write a story on how someone becomes cool. After some initial research, I began a tour around Pittsburgh, talking to cool people, hearing about cool places, clothes and things, and trying to learn a thing or two about what cool is.

The first thing I learned was that trends -- including matching underwear sets and many others -- might be cool for some people, but not everybody.

A second thing was it is much easier to discover what was uncool. Especially when it is staring you in the mirror every day.

The teacher of that important lesson was, not surprisingly, my wife, Jen. She bought me a splashy shirt a few years ago that I've never worn, even though it is perfect for a cast member of "Joseph and the Amazing Technicolor Dreamcoat." When she heard of my cool assignment, she said I now had to wear the shirt, and I quickly agreed. This greatly pleased her, until I said I'd also wear an old sweater over it.

"You'll never be cool," she said.

Prepare for backlash

The quest for cool is an international one.

A British firm put out a DVD box set in 2004 called "The Book of Cool" that includes step-by-step instructions on how to perform fancy tricks, from basketball and billiard shots to frisbee throws, skateboarding, juggling and quick-drawing guns. It is three DVDs and nine hours of remedial cool night school.

Being afraid of the above activities, I tried doing tricks from the chapter on "pen spinning" -- including tips on the forward thumb spin, the thumb snap and the fake reverse thumb snap -- but stopped after getting tired of crawling under my desk to hunt for lost pens.

It seemed that some of the other tips on the DVDs -- such as card tricks, or how to catch things with a lasso -- might be cool things to do, especially to attract the ladies at bars. To test this, I went to the Brillobox tavern in Bloomfield and asked owner Eric Stern if he had seen any patrons using lassos, and he said no.

Mr. Stern does see a lot of cool people, though. His bar is certainly among the coolest in Pittsburgh -- gilded with beautiful people, local art, good beer and kitschy videos on the big screen -- so I asked him for the formula.

"The vibe here is basically eclectic -- self-consciously retro stimulation," said Mr. Stern, a former Manhattan art gallery worker who moved back to town to open the bar with his wife, Renee, a fellow Pittsburgh native and artist.

The History of Cool Click image for larger version.

Mr. Stern's bar has become so cool that he sometimes faces cool's evil stepbrother -- backlash -- from some who think it's too popular and crowded. He knows that but presses on.

"We try to be as open-ended, eclectic and accessible as we can. We want people to feel good here. We don't want people to feel intimidated," he said.

Anatomy of an attitude

Cool has its dark sides.

Cool is a "permanent state of private rebellion," wrote the authors of "Cool Rules: Anatomy of An Attitude," a 2000 British academic study. And as such, those historically seen as cool share a sense of narcissism, ironic detachment and hedonism -- traits that might lead to a one-night stand, but not sainthood.

It can be dangerous or unhealthy. Cool figures from Humphrey Bogart to Tupac Shakur have always been associated with booze, smoking and violence. It also can be confused with being charismatic, something shared by Adolf Hitler and Jim Jones. (Not cool.)

Searching for it can also smell a little desperate. Something is wrong in our world if guys are trolling SeenOn.com -- the Web site that lists the clothes TV stars are wearing, with links to buy them -- and buying a $177 Theory thermal-front cashmere sweater because they think that it will make them look like Dr. McDreamy.

It is also confusing. In our post-ironic culture, who would figure that the Lawrenceville Moose and the Braddock Elks (the homes, respectively, of underground rock shows and happy hours hosted by Braddock's hip mayor) would be cool? Or that probably the coolest band that came through town last week -- Boom Pam -- played klezmer, Jewish folk music?

Even finding cool (or hip) people willing to talk about such things is a challenge, not to mention fitting into their clothes.

As 2003's "The Hipster Handbook" says, "the Hipster walks among the masses in daily life but it is not a part of them, and shuns or reduces to kitsch anything held dear by the mainstream. A Hipster ideally possesses no more than 2 percent body fat."

Clearly, this was not going to be easy.

Cool is myth

The American conception of cool is tied to the Jazz Age (from records such as Charlie Parker's 1947 "Cool Blues"), but its roots are older. The Oxford English Dictionary finds descriptions of cool people -- "not heated by passion or emotion ... undisturbed, calm" -- as far back as Chaucer and Shakespeare. Even ancient African societies had a version of cool called "itutu" that translates into a sort of grace under pressure, "Cool Rules" says.

So if being cool has been around for so long -- and most of us sense it when we see it -- why is it so hard to capture? I asked Charlie Humphrey, executive director of Pittsburgh Filmmakers, who did an essay on cool for the Post-Gazette a couple years ago.

"It's very much the same as the power of myth, because cool is myth," he said, sitting back in his messy (cool) office.

"It's not a matter of fact or fiction, it's the capacity or the power for meaningful change, embodied in an aura that is almost only told through narration, or metaphor, or symbolically."

Unlike Charlie, lots of the cool people I called never called me back, which I thought, in itself, is a pretty cool thing to do.

Those who provided help always gave it with caveats: We will tell you about cool clothes and other things, they said, but that doesn't mean they will magically transform you into a cool person.

Dannielle Romano, editor at large of DailyCandy.com, a site that has issued daily tips on cool things for seven years, pointed me to a bunch of stuff, including clothes by New York designer Steven Alan; cowboy boots from Justin Boots ("they're a basic for men you'll have the rest of your life," she said); and eco-friendly clothes from azaleaonline.com.

On the gadget side she steered me to a sun-powered charger at Solio.com, a fabric stowaway computer keyboard at goodhopebags.com, and rehabbed (but manly) dishes from Sarah Cihat.

Ms. Romano recommends "stuff that is really useful, designed with passion or love," she said, speaking from New York. "You should tell your readers something must be incorporated into their daily lives to be a must-have. Don't follow trends just for the sake of it."

Locally, Larrimor's co-owner Lisa Michael gave me a tour of her upscale Downtown clothing shop, stopping along the way at $50 vintage logo T-shirts, a $145 belt with a Fender guitar pick buckle, and a row of men's jeans from Diesel and 7 For All Mankind. We went over the fit of jeans, and how their colors are getting darker and less distressed.

But mainly Ms. Michael had advice: Don't plunge into something just because people say it's cool. Be yourself.

"If you're 28 and going out on Saturday night, you have a different definition of cool from someone who's 45 and going to dinner at the country club. It all depends on what you're comfortable with," she said.

"Like a woman changing her hair color, it's better to do it gradually, OK?"

According to the experts, cool cannot be forced, no matter how you look or where you go. Examples of cool-gone-bad abound, from people in so-called trendy clubs in the Strip District and the South Side to the Meatpacking District in New York.

"Trying too hard by definition excludes you from the potential pool of coolness -- you see every permutation of that in New York," said Ian Daly, an assistant editor at Details magazine. "Any time you see a reference to a quote-unquote hot spot, you're basically automatically referring to a mecca for poseurs."

I found Mr. Daly -- a funny guy who has covered culture, celebrities and more for the men's magazine -- through some common friends, and despite being a cool guy, he not only took my call but came through with stellar advice.

"The thing is, it all goes back to self-assuredness. The thing people forget is maybe at the high school in your little town, in the insular subculture that was high school, your coolness was defined by how accepted you were. Your only currency is how much the other kids like you.

"In adult life, in a big town like Pittsburgh or New York or wherever, the playing field is enormous and you can define cool yourself. That's why you moved to the big city. ... The thing we tend to forget is as we get older, we can define the parameters of cool, and knowing that is what makes a truly cool person."

A real cool person would learn a lot from Mr. Daly, but my mind began to wander. You know what would go great with that "Technicolor Dreamcoat" shirt? A matching underwear set. And a lasso.