Observation and emulation is the most natural way of finding your own style. The subtle danger lies in the fact that not all things that initially appear cool actually are. And us nerds, many of whom are sartorially naive, are vulnerable to duplicating things that may make them look bad, sloppy, or worst of all, like a tool. (IE. Don’t take style advice from Bret Michaels.)

Sticking with the Bret Michaels thing, a good first rule of thumb, one that should be obvious, is to avoid anything that is or remotely looks like Ed Hardy clothing. This rule should be unnecessary, but just in case anyone is in the dark on where Ed Hardy falls in the world of style, there it is. Big thumbs down.

Second, no flip-flops. Exception: If you are currently at the beach. This one is more difficult for me, because I live in a beach town, and it’s a lot easier to justify wearing flip flops as you leave the house if there is a remote possibility to of going to the beach later that day. You just never know when your friend might call you up and say, “WE ARE GOING TO THE BEACH NOW. NO TIME TO GO HOME AND CHANGE INTO FLIP FLOPS.” But I trust most of you don’t have the immediate lure of a nearby beach, and for you it can safely be said: If you’re going summer casual, get some docksiders. Nobody wants to see your toes. And for the confident nerd, espadrilles may also be acceptable, but are harder to pull off.

*extra note: Vibram Fivefingers belong in the Ed Hardy category of styleless awfulness. Unless if you are currently running in them, and seriously endorse barefoot running as a healthy alternative to running shoes, they should not be on your feet.

Third, no cell phone clips. Ever. Put it in your pocket or your awesome new bag.

Lastly, leather jackets. This is the one article of clothing that has the most potential to look amazing, but also to look unbelievable terrible. Before purchasing one, ask yourself, is this me? Does it fit my personality? Am I really just kidding myself? Have I ever been on a motorcycle in my life or do I have immediate plans to be? If you answered yes, yes, no, no, you may proceed with caution. Buy one that fits. It should be almost tight. Think Marlon Brando in The Wild One or Brad Pitt in Benjamin Button. And consider shelling out for a nice one. It’ll make all the difference.

The issue of leather jackets touches on an important element of developing your style: it’s yours. It’s good to notice what other people are doing and take notes, but it doesn’t always mean that what works for them will work for you, and what works for you may not work for them as well. Above all have confidence, and in time you’ll have developed a style all your own.

Geeks, more than any other stereotype, need a bag to carry all their crap (except for maybe your mom). Most geeks are not aware of this, and stuff their pockets so full of technology that when they’re required to empty them for airport security you’d think on first glance they were Inspector Gadget. Anyone remember Docker’s short-lived mobile pants?

The first order of business is the bag itself, and there are a lot of good options out there. You want some clean, simple, and classic, something that you can keep for a couple decades and it will only look better with age. Here are a few ideas.

Casual – Makr Tote

Believe it or not, it is now acceptable for men to carry tote bags. While this is casual, it will take the more confident geek to pull off. I have not completely jumped on the tote bag bandwagon, but black on black canvas and leather is about the manliest you’re going to get.

Business – Mismo M/S

You could throw this thing off a cliff and it would still look amazing. Just take your laptop out first.

Either – J.Crew Leather Postal

This simple leather messenger is the ideal choice to toe the line between business and casual. It’s easy to pull of, will look good anywhere, and the leather will only look more badass as it gets worn in.

I can guarantee that in guiding the transition from styleless nerd to put-together geek, these next few posts will be the most valuable ones I will write. These are the ground rules. These are the simple things that if abided by and tweaked, my work is done. The transformation will be so nearly complete, all that will be left is details.

I’m sounding like the Fairy Godmother throwing around words like transformation. I would write my own relevant lyrical rendition of that song she sang, but it turns out all the lyrics work just fine, considering most of them look something like this: Salagadoola mechicka boola bibbidi-bobbidi-boo.

Anyway, back to the task at hand.

The biggest problem men today have with the way they dress is that their clothes do not fit. I work in the restaurant business and see men stroll in day after day wearing suits that are at least two sizes too big. (For a pictoral example, hearken back to the picture in my last post of John Hodgman from Apple’s “Hi, I’m a PC” campaign.)

And the problem is not just with suits, it’s everything. Shirts are too big, jackets too baggy, pants too long. Geeks! Nerds! Men! You dramatically underestimate how much better you will look, and how much better you will feel, if you are wearing clothes that fit you. I am a tall man, and a myth I see perpetrated among my fellow gentle giants is that loose fitting clothes will make them appear smaller, when in fact the opposite is the case. And small men wearing baggy clothes look like stubble-faced children.

Geeks! Nerds! Men! You dramatically underestimate how much better you will look, and how much better you will feel, if you are wearing clothes that fit you. – Brandon

Let’s take pants for example. Your pants should not be a shapeless mass of cloth covering your legs. They should fit snugly, but not tight, and they should only break once as they’re hitting the top of your shoe. IE. If you’re stepping all over them in the back to the point where they shred into bits, they don’t fit right. Here are two examples of pants you should buy and pants you shouldn’t, taken from the same website (Lands End Canvas), worn by the same model.

Bad: (The key word to avoid with fit – roomy)

Good:

Need to confess to some of these poor practices? Let us know on twitter @codesketch or talk back on Hacker News.

Let me just say it. It’s okay to be a geek. Or a nerd. Really, you can be whatever you want. But what I’m trying to say is; you can still be your geeky, nerdy self and be cool. You can keep your Star Wars DVDs and plastic rimmed spectacles and be okay. Chic Geek is here to attempt to navigate the waters between the socially savvy, self assured brainiac, and the guy who doesn’t care.

Really though, you should care.

At least a little.

It helps.

It’s the difference between being this guy:

And this guy:

Depending on where you live, this look might get you laughed at. But don’t fret. You look pretty sweet. – Brandon

I mean, do you really want to look like a PC?

So, if you’re the kind of guy who tries to impress the females in neighboring cubicles with his USB powered rocket launcher, maybe you should stick around. You would have been better off buying the spork.

Editor’s note: We are pleased to announce that Brandon Joldersma will be joining Codesketch. He will be writing “Chic Geek”, a weekly commentary for nerds without taste. –Paul Hontz