How to Find the Perfect Khakis

James T. Murray

Departures goes shopping for the perfect designer khakis.

Nothing has made the transition from military to civilian life quite as successfully as khakis. They were born in service— Sir Harry Lumsden adopted the color in 1848 while he was commander of India’s famous Corps of Guides. They originally wore white, but, the legend goes, Lumsden noticed that the men who were the dirtiest were least likely to be shot by snipers. In the interests of troop survival, he ordered all his men to follow suit and dye their clothes dusty tan. Fifty years later British and then American troops began going to battle in khakis and have done so ever since.

They didn’t become an American classic until after World War II, when the GIs came home and went off to college wearing theirs. Then students and, as the old Gap ads pointed out, everyone from Steve McQueen to Pablo Picasso discovered what the soldiers already knew: Khakis could go anywhere—from class to club to beach—and looked right just about everywhere.

Which may explain why they were so easy to dismiss as the pants people settled for rather than the ones they chose. Now designers from Michael Bastian to Steven Alan to Brunello Cucinelli have updated the old warhorse with enough style to remind everyone that khakis, born of necessity, can also be objects of desire.

The Traditionalists

Brooks Brothers: This company started out making uniforms for U.S. veterans of the War of 1812. So by the time the khaki-colored chino became the Ivy League’s unofficial uniform, its version was already a classic. The Milano khaki doesn’t change the original formula much. They’re flat-front and cut slim but are now also washed and treated so no ironing is required. From $90; brooksbrothers.com.

Ralph Lauren: As seems fitting for a designer whose signature is the reinvented American classic, Ralph Lauren offers a multitude of khakis. There’s the classic flat front from the Polo line, as well as a style called the African Diary chino, which has subtle beading along the pockets and randomly placed patches. They’re beat up, torn, repaired, frayed, beautiful pieces of craftsmanship. You may, however, wish to put the miles on yourself. Enter the Purple Label five-pocket style. They’re not traditional—the five-pockets version is much more like a pair of jeans—but the cotton twill is Italian, the hardware antiqued brass and the cut slim-fit European. Polo, from $165; Purple Label, from $295; ralphlauren.com.

J.Crew: No company has done more to bring back American fashion heritage than J.Crew, and it hasn’t neglected khakis. The key is in the fit. The brand’s latest chino, the Urban Slim, features a trimmer cut than the baggy GI version, with a lower rise. But they’re still made from the original cotton twill. From $70; jcrew.com.

The Neoclassicists

Save Khaki: David Mullen’s cult brand occupies almost three shops—one is almost too small to count as a whole store—in Manhattan. The walls of all 2.75 of them are lined with his deceptively simple, slouchy namesake pants. They’re deceptively simple because his khakis are pretty much perfect. The fabric is incredibly soft, but it still has guts, like its military forebears. The cut is body-conscious but not clingy, producing a look that’s modern yet not ostentatious. And the Save Khaki United line is made in the U.S.A., so the pants are true to their cultural and stylistic roots. From $110; savekhaki.com.

Steven Alan: Few brands were marred by khaki’s Casual Friday image more than Dockers. Few designers are better suited to rehabilitating that image than Steven Alan, who made his name creating preppy classics with the ideal ratio of rumpled and retro-chic. The Modern Jod pants he created for Dockers have the details of the World War II version—button fly, straight side pockets, watch pocket and a loose (but not sloppy) fit—with a more contemporary tapered leg and a cropped cuff. These are for a casual Friday surfing on Montauk, and lounging by the bonfire afterward. From $130; dockers.com.

Michael Bastian: “The hardest thing to do,” Bastian says, “is to take something everybody makes and make it better.” He does just that in his khakis, with details like mother-of-pearl buttons and pockets lined with shirting fabric. While the material is still khaki, it ranges from a creamy, soft cotton with a silky, smooth hand to military-style cotton canvas. “I’m ready for khakis again,” the designer says. “They’re the ultimate American standard, after all.” From $395; michaelbastiannyc.com.

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The Europeans

Brunello Cucinelli: This designer is known for his ability to combine casual style and a luxurious finish. Applied to khakis, the result is just like the classic, only better. The buttons are real horn; the fabric is an enzyme-washed, two-ply Egyptian cotton. They’re not distressed; they simply look as if you’ve worn them for a summerlong boat ride in the Med, with slightly muted colors. They come in two cuts, one slim and one classic—both far more body-conscious and flattering than the GI original. From $625; brunellocucinelli.com.

Kiton: They look like khakis: same dusty color Sir Harry mandated, same pockets (four, plus a watch pocket at the waistline). But that’s where the resemblance ends. These pants are made by the same people who make Kiton’s suits, and they’re crafted with the same care. The buttonholes are cut and sewn by hand, as are the pockets, the interior stitching and more or less everything else. But all that’s your secret. The only way anyone will know these are something other than the casual American classic is by the fabric, which is at once silky and tough, and the fit, which is pure Neapolitan-style, long and lean. From $1,055; kiton.it.

Creating Custom Khakis

Bespoke tailor Jon Green on perfect custom khaki.

Khakis are as iconically American as blue jeans and, due to a prep-style resurgence, just as ubiquitous. Surely somewhere in a continuum from the Gap to Bottega Veneta it must be possible to find the perfect khakis. There are great off-the-rack ones, yes. Perfect? No. Manhattan-based tailor Jon Green explains the difference.

It’s simple: The only way to achieve the khakis you want is to go bespoke. A client recently had Green create a special pocket for his iPhone—one that didn’t make him look ten pounds heavier while carrying it and his wallet and keys.

Cut is king. The key to looking like a grown-up in the blue blazer–and–khaki uniform is all in the pants’ fit. After two to four fittings, they’ll be perfect: a lean, modern style that glides instead of binding; a loose cut that drapes smoothly instead of bagging (a common complaint).

It’s the fabric, sir. Green offers hundreds of swatches in season-appropriate weaves and weights, from classic twill to summer-weight 6.5-ounce cotton-linen to a 16.5-ounce cotton-cashmere for winter.

Details matter. And never more so than in something as simple as khakis: Waistband style, button or zipper fly, location of pockets and number of pleats are all points that are discussed and debated.

The truth: Clients generally first come to Green for a custom suit; most don’t even think about going bespoke for something as casual as khakis until they have a few pieces made. Bespoke addiction sounds improbable, but there must be something to it—Green recently made $30,000 worth of bespoke khakis for a single client. Allow three weeks; from $1,250; 212-861-9611.

An Ode to Linen

Tom Mastronardi’s ode to the glory of wrinkled linen.

Crisp, cool and comfortable on even the most daunting of summer days, linen is one of the oldest woven fabrics in human history. For the high purpose of the suitmaker’s art, let’s divide the linen world into Italian and Irish. The Italian version is lightweight (and arguably cooler), but at about 7.5 ounces, it doesn’t wear as well or as long as the more stolid Irish alternative. The best Italian linen can be found on Canali jackets (from $1,250; canali.it).

Weighing in at a hefty 13 ounces, Irish linen has a denser construct that wrinkles less and relaxes with more charm—a highly desirable quality to some. Legend has it that the most dapper sons of Erin would soak their jackets in water, then fill the pockets with stones prior to hanging them out to dry, hastening the breaking-in process. I recommend the Ludlow suit at J.Crew for this type of linen (from $260; jcrew.com).

In the end, it’s about what you want: the lighter, more louche Italian take or the Celts’ stalwart stability. The overarching lesson? Linen is meant to wrinkle. Live with it. Learn to love it. Ralph Lauren once saw to it that a tag was sewn into each linen jacket bearing his imprimatur, which rather brilliantly read “Guaranteed to Wrinkle.” Resist the temptation to press the fabric into submission. Trust me, you’ll lose. As for the argument that a linen suit should be relegated to more casual outings, The Bespokist offers this: Linen is best not confused with the more democratic company of seersucker, cotton or gabardine. —Tom Mastronardi