I’m one of the best-dressed people I know. No false modesty here. I’m not the best-dressed, partly because I can’t afford a really top-of-the-line tailor, and partly because I inevitably wear a little cat-hair, which some people believe is not in good taste if you’re a serious man of business. And some people would assert that I’m not well-dressed at all, because if I were, my clothes would not attract attention.

I would not advise most men to dress like me. If your profession calls for emphatically plain, ultra-conservative business attire, my look is not for you. If you don’t like it when strangers remark on your attire, ditto. Still, a lot of people have told me, over the years, that they wish they could dress like me (or wished they had the nerve to dress like me), and quite a few women have told me they wished more men would do so. As a public service, therefore, I’ll list just a few choices I make in putting myself together that I consider crucial. Some of these choices definitely break the rules-but it’s usually okay to break rules if you know you’re doing so, and why.

I consider cowboy boots perfectly acceptable for business. Most men look great in cowboy boots-more macho, more domineering-because of the pointed toe and the slight heel. No laces, so you get a cleaner look. And you never have to worry about the color or the condition of your socks!

President George H.W. Bush (“Bush 41″) favored cowboy boots with a business suit. He didn’t wear a bowler hat, as I do, but “Doc” Holliday and “Bat” Masterson did.

I always wear a hat-and for business, it’s almost always a bowler. It’s the first thing people notice about me, and it’s how they remember me: “The guy with the hat.” Many fashion experts say men should not wear hats with business attire, because they’re outdated and look silly. That’s nonsense. Certainly most men would feel uncomfortable wearing a bowler to work, but a good-quality fur felt fedora (not cheap wool felt) will lend authority to any man.

Most experts on business dress decree that your suit should be either blue or grey. Period. Maybe a tan suit in summer, but that’s it. In general I agree. But I sometimes break that rule and wear black, or white linen in summer. A man can’t carry off a black suit unless he’s distinguished-looking to begin with. To wear white, on the other hand, you have to have a hint of jocularity about your overall attire. (Think of Mark Twain, or James Whistler.)

I dress stylishly, not fashionably, and the key to that policy is to get your suits tailor-made. If you know where to go, you can get custom-tailored suits and shirts for not much more than you’d pay for off-the-rack, and they’re more economical in the long run.

Custom-made suits and shirts will last longer. Off-the-rack suits usually have some styling detail that will make them look dated in a couple of years, so that you have to give them to Goodwill and buy new ones. My standard “Joseph of Iowa” suit consists of a double-breasted jacket with roped shoulders, a waistcoat that buttons higher than usual, and trousers with a very long rise. You could never buy such a suit in a store. It’s emphatically different from modern standards, but it borrows ideas here and there from the past 100 years or so.

Because I have established this retro look, my clothes will always look current-for me-and thus I have suits I’ve worn for 20 years.

If you want to look your best, your clothes have to fit. Got one shoulder slightly higher than the other, as I have? Your tailor can take that into account. Got narrow shoulders and a big belly? An oversized butt? Do you walk with a stoop? Want to make your short neck look longer or your long neck shorter? A good tailor can’t change your build, but he can camouflage it.

Most critical, perhaps, is the fit of your shirt collar. Mortimer Levitt, the late founder of The Custom Shop chain of haberdasheries, once told me that the average man thinks his proper collar size is a full inch smaller than it actually is-so he buys his shirts accordingly, and strangles himself. That’s why men hate to wear ties, and look for any excuse to unbutton the top button of their shirts. If your shirt collar fits, you won’t even notice that you’re wearing a tie.

Probably next most critical are the length of your jacket sleeves and your trouser legs. Your jacket sleeves should show about a quarter-inch of shirt cuff when you’re standing straight with your arms at your sides. Asian men, especially, tend to wear their jacket sleeves half-covering their hands. They’d look more businesslike in a kimono.

To get the right length to your trouser legs-breaking over your shoe-tops but not enveloping them-always, always, wear suspenders. Never a belt. This is elementary, and yet so few men know what a huge difference suspenders make. For one thing, if you wear suspenders, you’ll want to buy your trousers bigger in the waist, and with a longer rise, which makes them more comfortable. That is, you’ll be wearing them higher-the top of the waistband just under your ribcage-and loose enough that they’d slide off if you didn’t have suspenders. Thus, your trousers will hang straight down your legs, and always to the length you want.

(If you wear a belt, your trousers will inch downwards, the bottoms will bunch up and flow over your shoes so you’ll tread on them, your gut will hang over your waistband, and you’ll look like a slob. Got it?)

I avoid dark shirts. Colored shirts are fine, but they should always be of a light color. Wear a dark shirt with a business suit and you’ll look like you haven’t quite grown up yet. And never, ever let your shirt be darker than your tie unless you’re actually trying to pass for a low-ranking Mafioso.

Carry two handkerchiefs: one for show and one for blow. Your for-show handkerchief can be plain white linen, folded to form a line across the breast pocket of your jacket, as President Ronald Reagan did, or you may use a colored silk square-usually of a color that relates to your tie-loosely stuffed into your breast pocket. I often choose a pocket square that relates not to the main color of my tie, but to an accent color. For example, if I’m wearing a blue tie with red and yellow stripes, I might choose either a red or a yellow hankie. Never wear a handkerchief that exactly matches your tie.

Finally, don’t fear to experiment. Sometimes you’ll buy a shirt or tie that doesn’t look as good on you as it did in the store. Those are your “fashion failures,” and you may give them away with a clear conscience. As you gain experience, you’ll have fewer of those-and more compliments, if you’re vain enough to care about such things.

-Joseph Dobrian

Tags: attire, BUSINESS, fashion, style, writing
Categories: Joseph Dobrian's Blog

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