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by Alex Via August 16, 2017

Much can be debated about how to wear shorts in a man’s wardrobe -- from whether they’re ever appropriate to wear at all, to how baggy is too baggy? How long is too long? Or short? Socks or no socks? And really, is it ever okay to wear cargo shorts anymore? We’ll attempt to answer these questions and review some general guidelines (which you are welcome to completely ignore because you’re a grown ass man).


In the long history of clothing and fashion, accepting shorts as part of an adult man’s wardrobe is still a relatively modern concept. The shift to include shorts as part of a man’s casual summer wardrobe began in the 1950s, but even then, it took some time to catch on). Before that time, shorts were reserved exclusively for young boys. While they’re common now in the U.S. and most of North America, in many countries, that reservation still applies.


Today, the cultural taboo may be gone (at least in North America), but there are still some guidelines around men’s shorts that will help ensure you’re wearing them well.



As a rugged gentleman, when are you in the clear to wear shorts and still be respectably dressed? The answer is simple: when there’s good reason to wear them. Thankfully, there are quite a few “good reasons”:


  • warm temperature

  • casual events

  • active or athletic environment

  • just because you want to, dammit.


When to definitely not wear shorts?



  • business dealings of any sort

  • formal ceremonies or events (if it requires a sport coat or jacket, shorts are a no)

  • when traveling to certain parts of the world (you’ll stick out like a tourist - and not in a good way).



What are your shorts made of? The material significantly influences not only the look and feel of the shorts, but also how they function.


  • Cotton, although soft and comfortable, is not always well-suited for wearing in the heat, at least not if you’re going to exert yourself. Since it doesn’t dry quickly, if (when) you sweat through it, those sweat marks aren’t drying anytime soon. Thankfully, there are various weaves of cotton, so depending on when you’re wearing it, cotton can still be a great option.

  • Seersucker, with its signature dimpled surface, allows maximum airflow, is one of the lightest cotton weaves available, and makes a fantastic material for summer shorts.

  • Twill is at the opposite end of the cotton-weave spectrum: a tightly woven cotton with minimal breathability means it’s durable, but it’s not going to be great in the heat.

  • Canvas is also durable, but it’s a lighter weave than twill, making it a softer, more breathable cotton option.

  • Corduroy (yes, corduroy) can be a unique addition to your summer shorts collection if you find a lightweight version that’s not too thick.

  • Denim: really? Unless you’re attending an 80s themed party, do not wear denim shorts.

  • Linen, a popular summer material, dries more quickly than cotton and is just as soft and comfortable. The downside is its affinity for wrinkling, so it’s tough to keep linen looking sharp; but, really, the goal of linen shorts isn’t really to look “sharp” anyway, right? The creases are distinctive to linen, and thus acceptable, so it’s fine to just roll with them.

  • Synthetic/Tech fabrics like nylon boast desirable features. Breathable, quick-drying, and sometimes moisture-wicking, a pair of shorts constructed of technical material is a top choice for any sort of athletic activity or environment.

  • Blends, such as cotton/linen or cotton/poly blends, can combine the best features of multiple materials (such as the wrinkle-resistance of cotton plus the breathability of linen). Of course you won’t achieve the full benefit of either single material (i.e. cotton/linen blends aren’t as breathable as full linen), but the benefit of the combination can be worth it.



When looking at how to wear shorts, we really mean, “How do they fit?” When choosing between long/short, slim/baggy, and other details, much will be determined by your personal preference -- but remember to consider your height and build (and where you’re wearing the shorts) to help determine the best cut, fit, and details of how you wear your shorts.


  • Length: There’s much debate over appropriate length for men’s shorts, and again, this will mainly be determined by your proportions -- but 2-3 inches above the knee to hitting just at the knee is an acceptable “safe zone.” Anything higher is too short (with the exception of some athletic shorts, but these should be reserved for the athletic activity for which they are intended). Anything long enough to hit below the knee, and you’re not technically wearing shorts anymore, so just don’t.

  • Fit: Generally speaking, shorts look best when they skim the body, providing enough room to move around, but not so much room that they appear baggy or sloppy.

  • Pockets: Gone are the days of big, baggy, cargo shorts. Like it or not, bulky cargo shorts propel you across the line from casual to sloppy. But, fear not, pocket lovers: there are plenty of well-fitting hiking and technical shorts with extra pockets and functional features. Today’s technical shorts provide a much cleaner look and fit, and with so many superior options available, there is no need to settle for the cargo shorts of old.

  • Pleats: No.

  • Colors and Patterns: Solid colors like khaki, navy, and olive are the most traditional style for men’s shorts, but plaids and brighter colors can be a fun addition to your summer wardrobe. Save the ultra-loud patterns (as in, Hawaiian-shirt-on-your-shorts loud) for the beach.

  • Socks: Yes or no? It depends. Obviously, if you’re in an athletic environment, then wear your socks and shoes with your shorts. Otherwise, shorts look best without socks. (If you’re wearing sandals, do not wear socks. If you’re wearing slip-ons like loafers or boat shoes, you still shouldn’t need to wear socks, but get yourself some invisible no-shows if you need them for comfort).


So, there you go. Gentlemen, we certainly haven’t settled (or even addressed) every debate that exists about how to wear shorts. (Let’s be honest, you’d probably ignore half of it even if we did.) But, one thing is certain: worn well, shorts can be a welcome addition to any rugged man’s wardrobe.


Alex Via
Alex Via

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