Just over a month ago, I ran into a friend at a CES event. While I see this friend around town once in a while, this was the first time I’d seen him in a non-casual setting since Blogworld 4 months earlier. After exchanging the usual pleasantries, he asked me an odd question: “Is this like your conference party outfit?”

Indeed, I was wearing the exact same clothes I’d worn to the event four months earlier. Since he doesn’t usually see me dressed up, it stood out enough for him to remember. But that’s not the real point, here; the real point is that I have few clothes suitable for “adult” gatherings.

I have a suit, of course, for weddings and funerals. (I haven’t had a job interview in 9 years, but if I did, it would be suitable for that, too.) And I have my day-to-day clothes, which aren’t awful but which aren’t anything to brag about, either. Functional casual, basically: jeans and khakis, an assortment of button-front shirts, some cotton sweaters.

As a college professor, there’s not a lot of pressure on me to dress up. If anything, it’s just the opposite. For one thing, I interact regularly with younger people, mostly teenagers (I teach 100-level courses), and being too formal creates a barrier between my students and me. That might be ok in business or law (think John Houseman in Paper Chase) but for my classes and my teaching style, some level of rapport is crucial. For another thing, my fellow professors don’t exactly set the sartorial bar very high – and there’s a certain sense of bohemian “me-against-The-Machine” attitude expressed by violating “corporate” standards of dress.

But mostly I dress the way I do because I’ve never really learned how to dress otherwise. Like a lot of my fellow geeks, fashion just wasn’t on the radar for me. Fortunately I have a brother who has always been very fashion-conscious, and he’d take me in hand every few years when my fashion sense got too out of touch with reason and social acceptability.

Well, my friend’s off-hand comment was a wake-up call for me. I mean, I’m a grown man – I should have more than one pair of slacks and one shirt nice enough to wear to an industry event without embarrassing myself! So I set out to educate myself on some fashion basics – what shoes go with what kind of trousers, how to distinguish various sorts of dress shirts, and so on.

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I did what any true-blooded geek does when he or she wants to find out about a new topic: I googled it. But what I found was scattered, often contradictory, and for a newbie like me, downright confusing. A lot of the information out there is tied to specific social contexts: the workplace, the nightclub, and dating, mainly. And a lot of it’s quite vague – the answer to most questions is “it depends on your personal style” which I’m sure it does, but what if you don’t know your personal style yet?!

With some perseverance, a few trips to department stores, and the help of friends on Twitter, I managed to assemble the following rules. As with all rules, they’re meant to be broken – but only by people who know how to break them. For the rest of us, this is a pretty good primer on basic men’s fashion.

Dress Suits

1. You eventually want to own three suits. Your first suit should be either navy blue or gray, possibly with a light chalk stripe (like a pinstripe, but softer), and in an all-season, medium weight. Either of these colors will fit into most social settings. Your second suit should be the one you didn’t get the first time around. Your third should be black – not for funerals, but for black tie affairs. If you work in a field where suits are the norm, you’ll probably want more than three; once you’ve covered the basics, you can move on to more distinctive suits (pinstripes, different weights, unconventional colors, etc.).

2. Suits are made of wool or cotton. Higher thread counts signify higher quality, but are ironically not as durable, so stick with something mid-range. Ask the salesperson to help you with this. (Yes, ask the salesperson. Suits are not self-serve.) Synthetic fibers need not apply.

3. You never button the bottom button. Apparently, Edward VII got fat and couldn’t button his vest over his belly, so now nobody does. On a three-button jacket, you button the middle; the top button is optional. If you have a jacket with 4 or more button, you obviously know what you’re doing already.

4. A gentleman carries a handkerchief in his front breast pocket. You don’t have to get fancy, just fold it square to fit and have 1/4” to 1/2” sticking out the top. Then proffer it as needed. And wash it after.

Shirts

1. Don’t wear your sleeves too short or too long. 1/4” to 1/2” of cuff should show beyond your jacket sleeve.

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2. Shirts with button-down collars are not dress shirts. They’re sports shirts, so wear them with a sports coat. Polo players used to button their collars down so they wouldn’t flap up in their face while they played. (Are you beginning to sense a theme here? Fashion rules are largely dictated by what English gentleman and nobility did generations or even centuries ago. Sports coats? You wore them during sport, i.e. hunting. Regimental stripes on ties? They indicated your regiment in the British military. And so on.)

3. If you unbutton your collar, remove your tie. You can wear a suit or sports coat without a tie – just ask Obama – but wearing a tie with an unbuttoned shirt looks sloppy.

4. You can unbutton the top button always (provided you’re not wearing a tie), the second button usually, the third button only on disco night at the Rollerama.

Trousers

1. Wear your pants at your natural waist. Too high and you look like Grampa, too low and you look like a high school kid. Your waistband should sit 2-3 inches below your belly button.

2. Pants should almost touch the ground without your shoes on. Jeans can be a little longer, since they shrink a bit when you wash them.

3. One pleat, maximum. If you’re a big guy, like I am, you learned somewhere along the line that pleats are slimming. They’re not. At best, they look like you’re a big guy trying to look slimmer; at worst, they actually make you look heavier because they pull out across you, broadening your appearance. In any case, the job of a pleat is to maintain that crease sown the front of your pants. For pants without that crease (and many with it), pleats are unnecessary; for pants that need the pleat, they only need one.

4. 1” to 1 1/2” cuffs. Or not. There’s nothing wrong with cuffs, there’s nothing wrong with no cuffs. They are understood, however, to be an older man’s style – not in a bad way, think sophisticated, experienced, distinguished, and conservative. For younger men, a cleaner line is generally preferred.

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5. A useful piece of trivia for the American abroad: in British English, “pants” are underwear. So if, for instance, you are in London and get invited out and maybe your trousers are dirty from work, don’t say “I’d love to go out, I just need to go home and change my pants first.” And if someone should ask, “Why, are your pants dirty?”, don’t say, “Yeah, I always get my pants dirty at work.” You will be laughed at. Er, I assume.

Shoes

1. Pay attention to your shoes. Everyone else does. It’s hard for the non-fashion-maven to tell a more expensive suit from a less expensive one, a high-quality shirt from a medium-quality one, and so on. But everyone can tell cheap or poorly cared-for shoes. Buy the best ones you can afford, and take care of them. Polish them regularly (a few swipes with a wax-infused polishing cloth is often all it takes) and store them covered if you won’t be wearing them for a long time. Shoe trees, it turns out, are important: they not only hold the shape of the shoe but the cedar ones absorb moisture (and thus odors) which helps preserve the leather. (Aside: women tend to pay a lot of attention to men’s shoes. Keep that in mind when a) dating, and b) interviewing for a job.)

2. Shoes are made of leather (besides sneakers). Anything not made of leather you can consider a non-shoe. Leather breathes and adapts to the shape of your foot. The soles don’t have to be leather, but the uppers do. (True story: as a young man, my brother was a car salesman here in Vegas. In the summer, the tarmac could get well over 150 degrees F. Standing out there with leather-soled shoes could give you second-degree burns! So they wore rubber soles, which melted after a month or two and had to be replaced.)

3. You need more than one pair of shoes, but not too much more. Black oxfords (lace-up dress shoes), black loafers (slip-on shoes), brown oxfords or loafers, and you’re set (not counting your athletic shoes, of course). A pair of ankle-high boots in black or brown can substitute for the loafers. Ox-blood (burgundy) shoes are harder to find but in theory go with everything. You can pretty safely ignore white shoes.

4. The shinier the shoe, the dressier. Matte-finish shoes – nubuck (that pebbly leather), suede, and distressed leather shoes are automatically compatible with jeans or khakis; shinier shoes might still go with jeans but it depends on the rest of your outfit, the dressier you are the shinier your shoes can be. If you can wear them with a suit, you probably can’t wear them with jeans, and vice versa.

5. Shoes should be the same tone or darker than your pants. This is all the rule you need to know when trying to figure out what shoes to wear. This is why you never wear brown shoes with black trousers, but you can usually wear black shoes with brown trousers. When in doubt, wear black.

Accessories

1. Match your belt to your shoes. It doesn’t have to be a perfect match, as long as you wear a black belt with black shoes and a brown belt with brown shoes.

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2. Match your socks to your pants. Again, it doesn’t have to be a perfect match – a little lighter or darker is fine. If you don’t have socks to match your pants, you can match your shoes, or just wear black socks.

3. White socks are for sports. Only. Unless you are a) wearing sneakers, and b) doing something athletic in them, avoid white socks.

4. Your tie should reach your belt. Anything short of your belt makes you look like a rube.

5. Try a front-pocket wallet or money clip. This will save wear-and-tear on your back pocket (helping to avoid the heartbreak of “buttsquare”), help avoid pickpockets (a little – the good ones know…), and save your back. Plus: classy!

6. You’re allowed one affectation. A fedora. A pocket watch. A bracelet or class ring. A vest (if you’re not wearing a three-piece suit). An expensive wristwatch. Pick one, but no more – give your whatever-it-is space to say whatever-it-says.

If it feels like these rules are arbitrary and stifling, they are. Think of it like learning how to paint: first, you do a still-life (arbitrary) using just one color (stifling). Eventually you move up to two and three colors, then maybe a warm or cool palette, and your subjects might expand to include figures or landscapes. Once you’ve mastered the basics, you can begin to press against the rules, juxtaposing non-complementary colors or painting unconventional subjects.

In fashion as in art – style emerges not from a lack of rules but from a mastery of them, from making them serve you instead of the other way around. If you’re a geek like me, you need to dial a fresh start – clear your closets of all those conference freebie t-shirts, put a shine on your shoes, and burn your butt-crack pants. Ultimately, these rules are not at all about tamping down your personality but about learning how to express it. And unfair as it is, people will take you more seriously when you dress with a modicum of style.

Anyone else have tips for the newcomer to the world of style? Give us your best advice in the comments.

QUICK UPDATE: Comments are coming on this post faster than I can get them modded in. If your comment was sent but doesn’t show up, don’t send it again – it’s in my moderation queue and I’ll get to it as soon as I can. Thanks – loving all the great comments on this post!