Style Guide: Flat Front Khakis

Unless you have to wear a suit every day, khaki pants are probably the real backbone of your work wardrobe. From formally tailored to comfortably slouchy, they go with almost anything, can be dressed up or down, and travel well.

Choosing the right pair at the right time is important, or you’ll quickly wind up looking like a chain restaurant waiter.

You’re all grown up now and you need some grown up khakis too. Generally speaking, “khakis” encompass a broad range of pants that fall into a category that traces it’s lineage to military trousers from the 1940s. American soldiers brought home these beloved and functional pants and crated a trend that culminated in the classic “Ivy League” look.

Your own goal with these endlessly versatile pants should be to look dressed up but still comfortably relaxed. Make sure they are reasonably trim and stay away from pleats. While they are starting to make a comeback for suit pants, the heavier cotton fabric of most khakis will cause the pleats bulge out and visually add weight and bulk to your midsection.

Flat front khakis will give you a leaner silhouette and also tend to look more dressy. You should look for a mid rise (meaning the crotch doesn’t hang down by your knees) and a natural waist (meaning the pants sit on your natural hips). Choose a classic strait leg and allow for a nice break that can work with heavy oxfords or casual boat shoes. For a cleaner, modern look, tailor the pants without a break – just make sure you’ll always want that style, because there is no going back.

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 in search of that elusive book on how to grow, say, marigolds and the freshly pressed crispness of heading off to the office on a brisk fall day, tweed jacket in tow.

While you typically want to keep to the classic fit described above, it makes sense to have both tailored and less constructed versions in the closet. 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 are one of the few clothing categories where I condone the “more is better” philosophy. Try to round out your wardrobe with different shades as well as styles; from light putty to deep British tan. Olive is a useful color as well. For the adventurous types who really love the classics, get yourself a pair of Nantucket Reds. While many brands may copy them, Murray’s Toggery Shop on the island itself is the original source.

While I generally don’t recommend specific brands, for the true American chino you have to check out what GQ magazine has called the “pants of the gods” - Bill’s Khakis. Go for the M2 model, around US $98. These pants are directly modeled after vintage World War II GI khakis and are built like Sherman tanks. They are about as authentic as you can get.