Newbie Fashion Tips for Grown-Up Men

2Just 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.

Accessories

71. 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.

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.

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