The Geek’s No-Fuss Guide to Better Dressing

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, ’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:


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.


  1. Damon: Truly, that’s why I’ve got a note on the Flickr photo reminding myself to get longer socks. Or, you know, pull up the ones I’ve got on.

    In my defence, I am sitting down with my legs crossed.

  2. I would think, if the geek is male and has a female SO (or a fashionable male SO), it might be good to give the SO permission to go shopping for him. Despite my own geekiness, I’ve seen every episode of What Not To Wear and can therefore apply it to everyone else on the planet, if not for myself. And I’ve done a decent job in buying clothes for men, when I’ve been asked to.

    There is one other point: it is not entirely uncommon for men to be colourblind; so for that reason alone, it might be better for them to outsource the shopping anyways.

  3. Here’s my one point about geek wardrobe choices: lose the white gym socks unless you’re actually going to workout. This includes leather shoes of any type – if you’re wearing leather shoes find something other than white gym socks.

    Can you really argue with Darren’s instant results? And look – no white socks!

  4. That is awesome!
    I would also agree with Gill’s defense of
    “What not to wear”. My father watched it and finally started wearing shirts that fit him, after years of my mother bugging him.

  5. I swear, one day I’m going to simply hire someone to buy me a whole new wardrobe.

    But first? I need to be able to AFFORD a whole new wardrobe. 🙂

  6. Heh, nice write-up Darren. I’ll admit that I’m far from being a fashionista myself: I have a tendency to opt for the standard jeans and a t-shirt ensemble, mated with a pair of clean running shoes. (I have a lot of tees.) Obviously, this outfit changes for special occasions. 🙂

  7. Great Mozilla shirt! Now if only they came in more stylish versions 😉

    I have to admit though, it’s tough to lose the clean running shoes. In the city, you can walk and run faster (not to mention be more agile) than all the other folks in pure business attire esp. dress shoes. Of course there are occasions where you wouldn’t bring the running shoes along 🙂

  8. Great post, while I admire the effort you have put into this, I feel that for some geeks it is just a lost cause (I’m thinking about many of my friends here). They are just too unwilling to get out of their comfort zones regarding their appearance, and try to use logic to explain their resistance (like everybody else is to blame for being so shallow and judging them on their appearance etc.).

    Basically I have given up trying to give them advice in this area: if they want to remain single and socially stifled then so be it!

    For the record here are some of my tips:

    1.Always buy expensive, well cut jeans. Don’t scrimp on these because they will last several years.
    2.Own at least 1 well-cut business suit (I have 3, more might be required depending on your job). Match the colour of your tie to the colour of your shirt! Silk ties are best.
    3.Buy black leather shoes for your suit, and casual brown leather shoes for everything else (including jeans, trust me as Darren says women always check out your shoes). Wear runners (or sneakers, sorry North Americans!) when you are going to the gym or actually running ONLY.
    4.Always polish your black shoes when you are wearing your suit!
    5.Buy a nice set of cuff links and a matching tie pin for special occasions. Buy a nice analog watch! Women (and some men) notice the details so they matter.
    6.Buy a good quality leather jacket, blazer style, ideally black. This can be worn over a white t-shirt and jeans or over a business suit, and still look smart.
    7.Try to get in shape! This will not only help with your appearance and health, but also your pose in the way your carry yourself. You want to project confidence: this attracts women and enamors colleagues to you. Don’t slouch your shoulders!
    8.Smell nice. Put odour eaters in your shoes, shower often, use deodorant, brush your teeth. A woman’s sense of smell is much more attuned than a man’s is.
    9.Never commit the cardinal geek crimes of wearing shorts, stained t-shirt, sandals, or tracksuit to the office, enough said!
    10.Be brave! You will be rewarded for your efforts.

  9. Fantastic post, Darren!

    I’d argue that along the line of shoes, one (male or female) could (depending on the formality of the occasion) wear a “non-athletic” sneaker (the slim puma-style shoe that’s fairly popular right now) with dark denim and still look quite dapper, especially paired with a well-tailored top. There is still no place for tall, white athletic socks, but an ankle-length athletic sock would be appropriate.

    Also, speaking of tailored things, make friends with your tailor. If you’re investing in clothes, you may as well ensure they fit you properly (more an issue with women I think, but applicable to men, too – especially with vintage pieces) and that you can have quality repairs done if/when necessary.

  10. Jen: I agree, though I’m trying to avoid the subtle decision-making for the geeks. What do you think of these? I bought a pair like those while in Budapest.

  11. Excellent post Darren- I meant to say that originally when you had us take a look at its pre-published glory.

    A great guide for any guy, geek or no (we all struggle with finding our own sense of cool), and who can argue with those before and after pics?

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