How to Wear Khakis With Style
Fit/Style. Khakis need not be high-waisted, pleated, or baggy. Instead, opt for a more modern style: flat front, with a straight leg, or a little taper from thigh to ankle, and an all-around more fitted and tailored look. The pants should have a mid-rise fit that sits around your hips rather than up over your belly button. And while khakis are meant to be a little roomier than other pants, you don’t want them to be baggy. They should offer a look that’s both relaxed and athletic.
Pockets. A pair of khakis should have four pockets — two in the front and two in the back. A small horizontal coin pocket is an acceptable addition on more casual khakis. Pockets on the sides turn them into cargo pants, which should only be worn if you’re actually engaging in tactical/outdoors pursuits. Cargo pockets add unnecessary bulk to your trousers, giving you a less sharp and streamlined look.
Wear. Khakis age well, and actually look better the more broken-in they get, hitting their peak handsomeness right before they start falling apart. So for casual clothes, it’s okay for them to show a little wear and tear — a few scars and some fraying on the cuffs add character. A little wrinkling is also natural and part of khakis’ insouciant look; under no circumstances should you iron a crease into them. When wearing khakis in a more professional setting, stick with a crisper and more unblemished pair (though you still shouldn’t iron a crease into them).
Color. Khakis come in just about every color these days, but the most traditional is drab brown. I’d recommend getting a darker brown, rather than a school uniform-esque golden wheat, as it’s sharper and more versatile (it’ll look appropriate in both winter and summer). Navy also looks very classic, and pairs well with a sport coat or button-down shirt. Beyond those two, you’re entering more fashion-forward territory; you need to know what you’re doing to pull off fire engine red chinos.
Add some visual interest to the neutral color of khakis with a belt. Leather, either solid or braided, looks sharp when you’re dressing up a bit. A fabric or ribbon belt pairs well with casual outfits.
Length/Cuffs/Rolling. Tailored cuffs add a little weight to the bottoms of your pants, look a bit more formal and conservative, and draw attention to your shoes. Avoid cuffs if you’re on the shorter side, however, as they make your legs look shorter. Generally, I’d recommend going cuffless, as it’s the most versatile style.
Top: Your khakis should skim the top of your shoes or drape 1-2 inches over them. Middle: If you plan on showing off your shoes, you might opt for a shorter leg length. Bottom: Example of khakis that are too long and excessively bunch around the ankles.
Cuffs or no cuffs, khakis should either just graze the tops of your shoes or drape 1-2 inches over, creasing a little at the hem. When wearing khakis in more professional settings, err on the side of a little longer. But they should never excessively bunch around the ankles.
Rolling up one’s khakis has become trendy in the last several years, especially among those who go sockless and want to show off their shoes. If you go this route, intentionally make the cuffs a bit “messy” and don’t roll them too high.
If you khakis are too long, you can make your own cuff by rolling them up, which has become trendy in recent times, and is something you can try if you’d like to show off your socks/shoes more, or simply keep your pants out of the wet/dirt. Rolling works best with slimmer fit khakis and those that are tapered (as opposed to boot-cut or a baggy wide-leg). For a tighter roll, roll once, pinch the fabric at the seam and fold it over, and roll it up again. Try a 1 to 1.5-inch cuff, doubled — too many rolls and it’ll look like you’re going digging for clams.
Dress them up, dress them down. You can wear khakis with everything from a t-shirt to a sports coat or blazer.
When going for a more formal look, choose a pair made with a fine, lightweight twill and trouser-like tailoring — a leg that tapers to the ankle, and possibly features details like a tab closure and cuffs.
When dressing up khakis with a blazer or sports coat, opt for one that is soft and unstructured, to match the casual nature of your pants.
Khakis match best with more casual, less structured, soft-shouldered jackets (think cotton, linen, corduroy). The more structured and formal a jacket is, the more it calls for a proper pair of dress trousers. When dressing up your khakis, pair them with a leather belt, and leather boots, loafers, wingtips, or suede oxfords.
Place a khaki blazer on top of matching khaki pants, and you’ve got a khaki suit, like this one from Apolis. A khaki suit is quite versatile: it’ll keep you cool at summer weddings, but, unlike other suits, you can mix and match the top and bottom, and wear them as separate pieces, creating a host of other outfits.
For a handsome look that’s between semi-formal and very casual, try wearing a button-down shirt, sleeves rolled up, with your khakis. You can’t go wrong with a crisp white dress shirt, but other colors and patterns look sharp as well. On the more casual end, choose a chambray shirt.
For a more casual look, choose khakis that are made with a thicker, more rugged fabric and have more a relaxed, utilitarian, militaristic style. Casual khakis pair well with sweaters, striped and solid t-shirts, polos, henleys, and denim or chambray button-downs. For footwear, throw on some leather boots, chukkas, canvas sneakers, or boat shoes. Wearing those last two options sockless with your khakis makes for a great summertime look.
When going for a casual look, henleys, striped tees, and denim button-downs look great with khakis.
Though it may be desirable to have one pair of khakis for more formal situations, and one for more casual ones, a single middle-of-the-road, not too casual, not too formal pair can work for all scenarios. The Effortless Gent has a great post on how a single pair of tan khakis can work in five different outfits.
Conclusion
I’ve hope you’ve come to see that khakis shouldn’t be pigeonholed as Casual Friday office pants. Strong and rugged, cool and comfortable, sharp and versatile, they’re date night pants, travel pants, errand pants — action pants and all-around adventure pants. Give ‘em a try and they just might become your new go-to pants.
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