A Tailored Guide to the Most Contested Two Inches in Menswear

(Bloomberg Businessweek) -- The correct length of a pair of pants, like a well-made ­martini, is a question of proportion. And like martinis, there are strong feelings about the right way to blend taste, trend, and tradition.

Historically, a wider trouser has been worn long enough to rest on the top of the shoe, which creates a break in the fabric in front of the shin. For years there was an uneasy détente between those who wanted this kind of “good break” and those who preferred “no break,” a cut that favors narrower trousers and runs parallel to the ground instead of falling over the top of your shoe. (Let’s not even get into the kind of break that gathers into an unruly pool of fabric around the ankles, evidence of a man struggling to keep pace with the world.)

I heard the phrase “a good break” before I knew what it meant. My father took me to the Polo store in Minneapolis when I was a boy and would tell Paul, our longtime sartorial consigliere there, that my trousers should have a good break. He said this with such confidence that I never questioned the validity of that declaration—and in any case, my preference wasn’t asked.

Eventually, I grew to prefer clothes that fit in a more concise way. I started gravitating to trimmer trousers with little break and, finally, to ones with no break at all—the hem was right at the top of the shoe.

That didn’t seem too controversial until last year, when I was standing in a renowned London tailor to be measured by the pant maker, himself a specialist in the art of ­trousering for over three decades. He made it clear, in an understated way, that he was disinclined to produce a pair without a break. When pressed to do so, he refused. And since I have a policy of not arguing with tailors, fishing guides, or anybody who has the keys to my car or apartment, the pants were returned to me with a compromise: a “slight” break, which is the equivalent of asking for a medium rare steak as opposed to one rare or well done.

Some no-break advocates believe the straight line down the leg makes a man look taller. According to Sid Mashburn, whose Atlanta-based men’s stores do a brisk business in suits, eliminating breaks in the line of the pants “visually lengthens one’s legs, making a cleaner line from toe to head.”

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Even dapper men who once wore a break are reconsidering their positions. Celebrated New York tailor Alan Flusser has always worn his dress trousers with a slight break. “I think it fosters a smoother and slightly elongating transition from the trouser opening to the shoe,” he says. But he’s evolving toward a break-free stance: “These days, with a slightly trimmer trouser than before, I tend to wear them almost straight, without a noticeable break.”

Michael Hill, creative director and an owner of Drake’s, believes it’s a generational thing. “Typically, younger men err on the shorter side, as that’s a slightly more fashionable, trend-driven look,” he says. “Older gentlemen tend to opt for a fuller length.” He adds that a shorter cut feels a little sportier, “a little more casual. It also affords the opportunity to introduce a pop of color with the choice of a sock.”

Then there’s the issue of seasonality. We deal with summer by giving ankles room to breathe with lighter loafers. Luca Rubinacci, creative director of his family’s renowned Naples tailor, wears pants with a break during winter, and in summer, he says, “I have them a little shorter with no break.”

But once you head north of the shoe and, more treacherously, north of the ankle, you have reached dangerous altitude. Blame is often laid at the brogue-clad feet of Thom Browne, the designer who shortened all of his suits.

Massimo Alba, the Milan-based designer, has his own line of clothes with an enlightened, relaxed sensibility, and he’s worn his pants the same way for decades: “Loose throughout the whole length of the leg and slightly—and when I say slightly, I mean really slightly—short,” he says. “They never rested on my shoes, perhaps two fingers above them.”

He’s opposed to the upward creep of tight trousers, however, since they restrict movement and are essentially impractical. “I find it extremely vulgar,” he says, “to see how working men are wearing some kind of hot pants that cling to their calves, thighs, hips and are cut off to show their ankles as if they were leggings.”

So, how high is too high? Patrick Grant, director of Savile Row tailor Norton & Sons, says his rule is that “the ­anklebone should never be fully exposed, in any circumstance, ever. If you don’t like long trousers,” he declares, “then wear shorts.”

To contact the editor responsible for this story: Justin Ocean at jocean1@bloomberg.net, James Gaddy

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