How to Dress Up Khaki
Credit: Courtesy Bill's Khakis

The khaki pant came into vogue in the Indian bush at the height of British colonial overreach in the mid-1800s. Cotton or linen twill dyed with mulberry juice allowed soldiers to blend into the arid landscape. By World War I, the fabric was a standard part of British and American military dress, and by the time World War II broke out, khaki pants were a casual dress staple. Still, getting these practical pants to look right can be surprisingly difficult.

Today, khakis come in a variety of fits, colors and styles, but the key to buying the right pair is finding khakis that can be either casual or formal. In an effort to figure out what makes a good pair of khakis work, we turned to Bill Thomas of Bill's Khakis, who might just be the fabric's biggest fan: "They go anywhere, do anything and are accepted anywhere," he says. "You'll never see a dress code that says 'No Khakis Allowed.'" 

Thomas says the first thing to look for is fit. Relaxed, baggy legs were common in the nineties but look bad with modern shirting. Opt for a straight leg that doesn't add too much volume to the thighs, and a leg opening that doesn't cover up your shoes. If versatility is what you're after, avoid cargo pockets, which "take the conversation in a whole different direction." A straight-leg khaki is a universally accepted fit that looks as good on larger guys.

And once you've found a good straight-leg fit that works for you – Bill's Khakis does a good one, as do J. Crew and Incotex if you're willing to spend a bit more – maintenance is key. Adding a crease down the front, by either dry cleaning or laundering then ironing if you plan on also wearing a blazer. If casual is what you’re going for, don't be turned off by wrinkles. If you're finding that frequent use of the drying machine is leaving your slacks a little snug, here's a great tip on using the dryer from Thomas: "If your khakis get shrink up too much, hang them dry. They'll come back."

 The final trick to dressing khakis up the right way? Accessories. Make sure you're wearing a leather belt and matching leather shoes – think derby or wingtip – and avoid lighter socks. Contrast at the top and the bottom will highlight the pants themselves, which is ideal given the fabric's long-established appeal. [Sunbleached Twill Khakis, $175; billskhakis.com]