Khakis: Pants to Live By

For many of us, khakis are the real backbone of our wardrobe. Workplace to casual wear, they go with almost anything, can be dressed up or down, and travel well. In many ways, they are the perfect pants.

Jeans have their place, no question, but khakis have that preppy, laid back good-with-a-sweatshirt-or-blazer thing that’s hard to define.

Choosing the right pair of khakis at the right time is an important challenge for some men, and the risk of looking like a chain restaurant waiter can be a real one. A good way to start the process is to treat your choice of khakis as a grown-up one. Think about this wardrobe staple as you would any other clothing investment and make a smart choice based on quality, fit, style, material, and cost.

When you think about it, unless obligated to wear a suit every day, the go-to staple of most mens’ office wardrobes are khakis. Also referred to as chinos, especially when denoting dressier versions, these ubiquitous trousers are available in myriad styles, from loose and comfortably old school to trim and tailored.

Generally speaking, “khakis” encompass a broad range of pants that fall into a category that traces its lineage to military trousers from the 1940s. American soldiers brought these beloved and functional pants back home and created a trend that eventually morphed into the ironically classic “Ivy League” look. These days, the term encompasses the general style of pant now available in an endless range of colors, finishes, weights, and cuts.

Your own goal with these endlessly versatile pants should be to look dressed up but still comfortably relaxed. Ideally, this translates into khakis that are reasonably trim and have a flat front. While pleats are very much a personal choice, for many men they remain unflattering and dated when applied to casual pants. While they are making a bit of a comeback for suit trousers, the heavier cotton fabric of most khakis cause the pleats to add visual weight and bulk to the wearer’s midsection.

Bonobos in particular makes an excellent range of khakis that employ the brand’s signature curved waist that removed much of the pants bulk. The result is a very comfortable and well-fitting pant that also looks trim and modern.

Flat front khakis will give you a leaner silhouette and also tend to look dressier. A mid-rise fit and natural waist help to create a comfortable and crisp look. A classic strait or lightly tapered leg continues a more tailored and modern look and allow for a sight break that can work with oxfords or boat shoes. The no-break look favored by some seeking a tailored mod effect can work, but it makes no allowance for error or physical changes, so be forewarned.

In many ways, khakis are the all-purpose chameleons of your daily wardrobe. They can impart both the rumpled comfort of puttering around the library and the freshly pressed crispness of heading off to your office on a brisk fall day, tweed jacket in tow. So, it makes perfect sense to have both tailored and casual versions of khaki pants in the closet. Jack Donnelly makes classic khakis built on the traditional WWII-inspired silhouette, but updated for a contemporary fit.

Seasonality plays a role as well; lighter weight 5.6 ounce fabric are best for warm months just as classic 8.5 ounce pants can be pulled out for the fall and winter.

Khakis also fall into that rare (at least for us) “more is better” category, due to the plethora of colors and finishes available to men today. Try to round out your wardrobe with different shades of khaki – from light putty to deep British tan – and try out some colored varieties like olive, navy, and orange. For the New England purists, who value the classics, a pair of genuine Nantucket Reds from Murray’s Toggery Shop is, of course, mandatory.