Walking Shorts for Men: The 3 Essentials

Yes, men, it is possible to wear walking shorts and look every bit as stylish as you do on those days of long pants and blazers.

But not many men know this, which has led to an altogether lack of optimum walking shorts attire. You’ll see vacationers donning khaki shorts with sneakers and white athletic socks. Or maybe you’ll make the mistake of bringing a casual pair of khaki shorts to a tennis match when what you really need are some performance shorts.

How do you know which walking shorts are appropriate to which situation—and what to wear with them? By keeping yourself together with just a few of our walking shorts tips:

The Three Categories of Walking Shorts

First things first: you need to know that not all khaki shorts are alike. They may look alike, but underneath their construction is a layer of subtlety that’s lost on the casual style enthusiast.

The three categories are as follows:

Basic Khaki: No-frills, but as versatile as anything in your wardrobe. There are two color options—a near-white khaki and a darker khaki—but we’ll leave that choice to your personal taste.

Performance: More athletic, featuring a split waistband and seat. Their wrinkle and stain resistance is also important for staying active. These are the walking shorts you should take with you if you actually plan to do a lot of walking that day—consider these your official “golf course” shorts.

Washed Khaki: These have something of a rugged, “worn” look to them that’s very popular these days. The enzyme and silicone washing helps promote durability as well as overall attractiveness.

Our style advice? These khakis are identical enough to the untrained eye, so you can get away with wearing just about one of them in a number of social situations—backyard barbecues, casual day at the office, etc. Some of the choices depend on your taste—are you a “basic” or a “washed” khaki man, for example?—and others depend on pure function, as is the case with the performance khakis.

Tips for Pairing Walking Shorts with Tops and Shoes

Get yourself a well-fitting pair of khaki shorts and you’ll have more sartorial staying power than the typical man wearing cargo shorts or jean shorts. But that doesn’t mean your fashion journey is over yet. Here are a few more tips for making your walking shorts mesh with your outfit:

Go sockless. If you must, wear low-riding socks with your shoes—just don’t let your socks show. Wearing socks with shorts has become a major stylistic no-no in this day and age, both because of its ubiquitous usage and due to the fact that it makes you look like you’re headed to an impromptu basketball game.

Belts are optional. Many men have grown up using belts all the time, but the truth is, if your shorts really fit you well, they’ll stay up even with a belt. If you do wear a belt—make sure to match it to the color of your shoes for uniformity. Dark brown with white khaki is a go-to option that won’t fail you.

Upgrade the t-shirt. T-shirts are great, they’re functional, they’re comfortable—but something about a good pair of walking shorts demands a collar. At the very least, a polo shirt will dress you up without impeding your ability to kick back and relax.