A Guide to Buying and Wearing Shorts for Men

Mens shorts buying guide

There's a lot of hate surrounding shorts in the world of men's style.

Tom Ford, the famous designer, has been quoted saying something to the effect of “shorts are to never be worn outside of the tennis court.”

All due respect to Tom Ford, I say fuck that!

While I do take pride in being appropriately dressed, I also have a fundamental problem with ignoring practicality.

So I drink water when I'm thirsty, wear a parka when it's bitterly cold, and damn it if I'm not going to wear shorts when it's blazing hot – tennis match or no tennis match.

But it helps to conform to some of the rules.

When are shorts appropriate?

Practicality aside, there are some situations where shorts just aren't the right choice.

In decades past, it was universally considered bad manners for a grown man to wear shorts outside of athletic endeavors.

So I feel lucky to live in more relaxed times where you can see downtown streets packed with men wearing weather appropriate shorts instead of stifling three-piece suits.

However, there are certain situations where I would tend to agree with Mr Ford. Weddings, offices, and upscale restaurants all call for long pants.

Given how infrequent these restriction are, though, I'm happy to comply.

Excluding professional offices, most guys can wear shorts nearly round the clock in the summer without fear of looking like a school boy in short trousers. Great for us!

Buying the right shorts

A Guide to Buying and Wearing Shorts for Men

Of course, any old shorts will keep you cooler. But since we're essentially getting away with murder by traditional menswear standards, I think it's important to pay attention to the details.


The material of your shorts is going to determine the look, feel, and perhaps most importantly, how the fabric functions in the heat.


Cotton is the default clothing material. It's smooth, comfortable, easy to care for, breathes relatively well, and looks sharp enough in casual situations.

But for typical summer conditions, cotton isn't the best choice. The major downside is that cotton doesn't dry quickly, or at all if it's humid and you continue to wear it.

So if you happen to get caught in the crossfire of a water-balloon fight, you'll be walking around in soggy shorts for the rest of the day.

And that also means that if you happen to suffer from the unfortunate event of visible crack sweat, that dark line isn't going away until you have the opportunity to change.


A Guide to Buying and Wearing Shorts for Men

Linen is the hot weather super star. It's the material of choice for tropical and dessert dwellers around the world. It breathes better than cotton and dries much quicker.

The downside? Linen clothes wrinkle like crazy!

But the upside is that this isn't necessarily a bad thing. Think about how a few scuffs on a pair of boots is a sign of quality leather.

Likewise, linen has a distinct wrinkly texture that signifies that you're wearing dedicated summer clothing. Or in other words, you take your style and comfort seriously enough to have specialty items.

So the sooner you accept this as part of linen's charm and allow it to become a hallmark of your rumpled carefree summer look, the better off and more comfortable you'll be.


You can also split the difference with a cotton/linen blend. You'll get the breathability and moisture management of linen with the wrinkle resistance of cotton.

Of course, you won't get the full benefits of either while retaining a portion of the drawbacks of both, but it's a good compromise if you want improved performance but don't want to go full linen.

Tech fabrics

To men's style purists, synthetic fabrics are typically viewed as uncomfortable, sweaty, and cheap looking. And that was mostly true – until recently.

But the performance and tech fabric craze has pushed synthetic materials forward and they've come a long way, often outperforming the natural materials listed above.

A North Face fleece jacket is the perfect example. Sure it's made from synthetic materials, but it's also super comfortable against the skin, doesn't shrink in the dryer, and is warm and breathable at the same time.

While natural fabrics are still the most common, you can't stop progress. So expect to see more tech fabrics being used to create traditional casual garments in the future (like these hybrid shorts).

Cut and length

A Guide to Buying and Wearing Shorts for Men

As you can see, baggy cargo shorts don't look good on anyone!


Shorts look best when they skim your body, providing you with enough room to move freely without being excessively baggy.

Look for shorts labeled as “tailored” or “slim” fit to avoid the Doug Funny look (as I've taken the liberty of illustrating in the old photo above).

The ideal inseam

A Guide to Buying and Wearing Shorts for Men

The sweet spot for most guys is going to be an inseam length of between 7 and 11 inches (for simplicity, it's usually clearly labeled).

A 7” inseam is about as short as I would advise wearing. That'll put the hem high enough to show off your work in the squat rack, but they'll be long enough to be seen as respectable.

On the longer end, a 10 or 11” inseam should hit just above, or right at the knee. If you're just now ditching long, baggy shorts, this is the perfect starting point.

Tall guys

Beyond personal preferences, you should also consider your body type.

Taller men should avoid shorts with less than about a 7” inseam (erring closer to 11″) because the shorter inseam will just exaggerate their already lanky legs.

Shorter guys

Short men usually gravitate toward larger clothes, but that's a mistake as it only makes a short stature more obvious. I would strongly suggest that they consider a shorter inseam – somewhere nearer the 7” mark.

A shorter inseam will actually help to lengthen their frame by avoiding a hand-me-down aesthetic.


Basketball and other pure athletic wear are obviously out for a smart casual look, but there are a few other details to consider.

In short…


  • dated plaid patterns
  • loud colors
  • excessive pockets and drawcords

Look for

  • solid colors
  • subtle patterns
  • clean design details

When in doubt, go for shorts which look like office chinos that have been cut off above the knee. Choose neutral and muted solid colors.

If you have the confidence and desire, feel free to experiment with bolder options. But for those just wanting to look sharp, it doesn't have to get more complicated than the above recommendations.

Shorts styling resources

A Guide to Buying and Wearing Shorts for Men

For those in-between weather days, wear a shawl neck cardigan as a light jacket (buying guidelines can be found in my free ebook).

If I'm wearing shorts, I'm most likely also wearing boat shoes. Check out this article for everything you ever wanted to know about boat shoes.

For other shoe options, I wrote this article covering the 5 essential summer shoe styles.

When you want to dress things up a bit, a short sleeve button down is the perfect option.

For a simple casual look that perfectly complements your wisely selected shorts, choose a fitted t-shirt.

The ones I wear most often are from Target (about $10 each). For reference, I'm 185 lbs and a medium fits me true to size.

A Guide to Buying and Wearing Shorts for Men

Where to buy shorts

At the end of last summer, I had to throw out all of my shorts because, like most of my jeans, they were blown out or wearing extremely thin on the inner thighs.

So after the first 70 degree day, I headed out to buy a new rotation of versatile shorts to carry me through the season.

I don't get particularly excited about shorts (the way I do about boots) and don't view them as items worth significant time and money investments.

A Guide to Buying and Wearing Shorts for Men

So when the need arose, I just stopped into Old Navy and walked out with 5 pairs in less than 30 minutes for under $100.

If you need quality in every aspect of your wardrobe, feel free to look into some higher end options. But, in my opinion, they're really not a category that requires a ton of cash spent in order to have sufficient options on hand.

What if you have small calves?

A Guide to Buying and Wearing Shorts for Men

I'm sure you've noticed that I don't have outstanding calf development (I know Instagram haters haven't, haha!).

I actually used to feel very self-conscious about my terrible calf genetics, refusing to wear shorts between the ages of 10 and 21 despite the soggy Midwestern summers.

After years of grueling calf workouts with minimal changes, I eventually accepted that calves are largely dependent on genetics. 

So my calves aren't massive, but who cares? I'm not going to sweat my ass off just to cover up a part of my body that I'm not thrilled with.

We all have weak points. All you can do is accept what you have and do what you can to improve.

I only bring this up because I know a lot of guys are concerned about having small calves.

So if this sounds like you, please don't let those insecurities stop you from wearing clothes that are comfortable in the heat. Ignore the haters!

All the best,


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  • Reply
    July 12, 2016 at 3:29 pm

    Great article and it clears up some issues I had regarding fit for shorts. I’ve traditionally been a cargo short wearer but they always felt sloppy. So I’m looking forward to having some more stylish options. Thanks Nate!

    On a side note I can’t imagine going back to life before boat shoes. I started wearing them after reading your article about them and haven’t turned back since. What a great shoe.

  • Reply
    Keith Garrett
    July 14, 2016 at 7:49 pm

    I bit the bullet and purchased some chubbies… The quality is meh but the fit is great. Keep the blog going!

  • Reply
    Austin Turner
    September 4, 2016 at 7:44 pm

    My legs are short, thick, angrily muscular, and hairy. Whenever I try the shorts suggested, they are super tight and just short enough to expose the heads of my quads, making my legs look shorter, thicker, more pissed off, and just as hairy. How/where do I start looking to find a better fit, without going full cargo?

    • Reply
      September 6, 2016 at 8:06 pm

      Lol! The angry legs description genuinely made me laugh. In your case, you could definitely look for shorts that are a little longer to hide your angry quads. I would recommend that you just go to the mall and start trying shorts on until you find the pair that looks best and stock up on those.

  • Reply
    October 7, 2016 at 5:33 pm

    Thanks for posting a great article about shorts, Nate!
    For a man who live in the Philippines, shorts has been my weekend clothing staple (except when I go to church on Sundays). I am big fan of UniQlo shorts because of the low priced, high quality cotton on their shorts. But, I’m planning to get two pairs of tailored shorts in February 2017.

  • Reply
    December 3, 2016 at 7:17 am

    Nate, you’re spot on regarding linen. I bought a pair on a whim at a J. Crew Factory store last summer. Went back the next day to buy a pair in all of the other colors they had (ended up paying less than $17 / pair). I only have one pair of cotton shorts (not entirely true as a I have a lot of “novelty” shorts from Chubbies) that I wear with any regularity (and that’s mainly for fall when the sweat factor is diminished).

    • Reply
      December 6, 2016 at 5:16 pm

      I’m glad you’ve experienced the benefits of linen! Once I got my first linen shirt that’s all I wanted to wear in the summer.

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