DarrenBarefoot.com

By reputation, IT professionals are lousy dressers. Wander into any software development office, and you’ll be able to verify this first-hand. You’ll see plenty of sneakers, jeans and shabby, XML.com ‘98 t-shirts. You may even spot a few utility belts.

It doesn’t have to be this way. I’ve got a strategy for improving the average geek’s wardrobe. This approach should appeal because it’s:

• Simple
• Brief
• Reliable

It’s “What Not to Wear” meets Linux.

Before I continue, some disclaimers:

1. Lord knows that I’m no fashion plate.
2. There are plenty of geeks who do dress distinctly and impressively. This article isn’t for them.
3. There are plenty of non-geeks who are shabby dressers. This article applies to them, too.
4. There are plenty of girl geeks, shabby and sharp dressers alike. The general philosophy may apply to you, but the specifics probably don’t.

Why Bother?

Geeks are generally smart. I think, for the most part, they opt to expend their brain power on activities other than becoming sharp dressers. That’s fair enough.

Like it or not, though, clothes are important. Clothes are costumes. And costumes, as comic book readers know, are symbols. And symbols have power.

People judge you on your clothes. Everybody does–employers, employees, mates, potential mates and so forth. The world cares how you dress, even if you don’t. And that might mean the difference between getting the job or the girl (or boy, if that’s the way you trim your jib).

Plus, why spend so much time outfitting your World of Warcraft avatar (”I simply must have the Level 70 Shoulders of Fabulousness”) and so little time dressing yourself?

Outsource Your Shopping

Geeks like do-it-yourself. Consider the success of Make. We like to learn how to solve our own problems.

That’s not okay here. In sartorial matters, you need to outsource.

Why? Because you’re busy, you’re under-motivated and there’s too much to learn. The goal here is simple: ensure that you look cool with a minimum of effort.

It’s a two-step process:

1. Identify appropriate stores to shop at.
2. Visit stores, and put yourself in the hands of the people there-in.

Step 1: Find the Right Stores

This is where you have to do most of your work. Don’t worry, you only have to do this about once a decade.

You need to identify a few stores (say, less than five) which you will exclusively shop at. Here’s how:

• Check the fashion articles in your local alternative newspaper (in Vancouver, that’s the Georgia Straight). Find out where the clothes were obtained from.
• Ask your female friends who among your male friends is the best dresser. Find out where he shops.
• The stores should be independently owned–no chains, franchises (at least none that expand beyond your own city) or national brands. Otherwise, apathetic 14-year-old girls will be choosing your clothes.
• The stores are unlikely to be in malls. They’re probably in downtown cores as opposed to the suburbs.
• Include one vintage store (vintage is a fancy word for secondhand clothing).

In Vancouver, a few qualifying stores would be You and Whose Army, John Fluevog, Front & Co and Discollection.

Step 2: Surrender to the Fashion Experts

Your toilet’s broken (it’s not really, but imagine it is). You don’t have time to fix it, or to learn how to fix it. What do you do? You outsource the work by calling a plumber.

Do the same for clothes. Go to the aforementioned cool stores, find some clerks that you like, and put yourself in their hands. They know what they’re talking about.

We’ve chosen independently-owned stores because the staff there hang around longer, and tend to be more informed.

Emphasize the following:

• You don’t like shopping, so let’s get this over with quick.
• You’re not looking to be ultra-hip. You want cool clothes that will last.
• You don’t want to make any particular statement.

Trust their instincts.

A Few General Tips

Above all, trust the experts in Step 2. In closing, though, here are a few general tips that may help:

• Buy cool shoes. Great shoes upgrade an outfit by, like, one whole version number. Plus women always (always!) look at shoes.
• Buy clothes that fit. Again, trust the experts in this department. They’ll choose items that flatter your body shape.
• A nice jacket (as in a sports jacket or ‘blazer’, if you like) dresses up any outfit. Buy two nice ones, and they’ll last you for years.
• Buy fewer, more expensive clothes. They’ll look better longer, and you’ll have to go shopping less often.
• Don’t forget the accessories: sunglasses (these date very quickly, fashion-wise, so be careful), belts, bags and cuff links. Avoid bracelets–they’re for Senior Fashion Architects only.
• Don’t bring your significant other. They’ll just prolong the experience, and how do you know their fashion sense is any better than yours?
• Spend more than $20 on your haircut. Just trust me on this one.

Experience Instant Results

Check out what this strategy did for me:

Before

After

UPDATE: I was remiss in not thanking a few people who looked at this article and provided feedback before I posted it. Many belated thanks to Kris, Julie, Jordan and anybody else in the Vancouver Tech Swarm that I missed.