In the recorded history of mankind, it has never been harder to be cool than it is today. When I was growing up, it was easy to be cool. You found the coolest kids in school of your gender and you did exactly as they did. You wore what they wore, ate what they ate, watched what they watched, and listened to what they listened to. Provided you weren’t born with some hideous physical defect, such as red hair or freckles, you could rest easy. You were cool.

It’s not as easy today. With the advent of the Internet, a thousand television channels and countless streams of information flying in from every available wavelength, the definition of cool changes from minute to minute, if not second to second. You cannot simply locate the cool person in your age and gender group to emulate any more. By the time you find them, they will be out of fashion.
Never fear. There are a few unassailable guidelines for how to be cool. These immutable laws of coolness never change, and as long as you adhere to them, you will be at least chilly, if not downright cool.
The first rule of cool is that appearance is everything. If you look cool, you are by definition cool. This is not as easy as it sounds. For instance, what is cool for a 13-year old is not necessarily cool for a 33-year old. When traveling at the mall – where you must appear at least once a week in order to keep your cool quotient – you will note that most teenage boys wear their pants about halfway down their thighs.

For them, this is cool. For you, this is an excuse for mall security to post your picture on a bulletin board in their office. The general rule of thumb here is to always dress as if you were going to visit your mother. If she would tell you to pull your pants up, pull them up.
Your clothes should have someone’s name on the outside of them. Preferably that of a one-named entity that you’ve probably never heard of like Sean Jean or Tommy Hilfiger. If your clothes have your name on them – on a tag inside – that is definitely not cool.
Shoes are essential for coolness. Canvas high-tops are very cool, as long as they are from Chuck Taylor and not Target. Velcro is okay on pants, but not on shoes. Velcro shoes prevent coolness in any male between the ages of six and sixty.
Technology is cool, as long as you don’t admit that you know how it actually works. Having an iPhone is cool. Using it to text is also cool. Complaining that it doesn’t access the 3G network is definitely uncool. Speaking of texting, it’s very cool to be able to type with your thumbs. It’s extremely uncool to ask your kids what “OMFG” stands for. It’s even less cool to be shocked when they tell you.
When it comes to digital entertainment, the following are cool: YouTube, TIVO, The Office, IPod, ITunes, Face Book, MySpace, TMZ, The OC, Gossip Girl, Lost and Bit Torrent. If you can speak intelligently or at least cogently about these topics, you will remain on the cutting edge of cool for at least the next twenty minutes or so.
Not as cool are MTV, MSN, The Simpsons, South Park, stick phones, American Idol and WWE. The tricky part is that all of these things were cool within the last year, so you have to be careful. Being current is an essential part of being cool.
The last rule of how to be cool is “cool is as cool acts.” If you act cool, you will likely be cool. Exude coolness in all you do. Never doubt yourself for an instant, for if you do, all is lost. Do not question your coolness. If you have to ask if you’re cool – you’re not.