How to Wear Shorts

How to Wear Shorts

Wearing shorts is one of the best ways to stay cool during the summer. Shorts are perfect for weekend shenanigans, dog walks, the beach, the pool, barbecues, picnics, romantic walks in the park…you get the point.

Shorts are inherently casual, but that doesn't mean they have to look adolescent and sloppy. So why do most men look so bad wearing shorts?

Shorts bad fit

Well, they're just not wearing them correctly. Their shorts don't fit, and they're not wearing the right styles.

This post teaches you how to avoid these mistakes so you look amazing wearing shorts like the laid back, stylish gent you are!

How Shorts Should Fit

To make sure your shorts flatter your body type, you need to pay attention to the length AND the width (the leg opening).

Shorts Length

Just like with swim trunks, it's crucial that your shorts don't go past your knees. They should stop at the top of your kneecaps (at the longest).

Ideally, your shorts will stop an inch or two above your kneecaps, but this is a matter of personal preference.

Correct length for shorts

shirt (old) | shortssunglasses

Just like pants, the length of your shorts is measured along the inseam. The best length for men under 5'9″ is 7″.

Anything longer than that will most likely be too long, although you can get away with 9″ shorts if you like them a little longer.

If you're under 5'5″ or just want to show a little more thigh (highly recommended) you might want to wear 5″ shorts instead.

Shorts Width

Shorts too wideAfter wearing shorts that are too long, the second most common mistake that guys make is wearing shorts that are too wide.

Just like pants, most mass-manufactured shorts will be too wide through the leg. Unless you have thick legs, you'll need to look for “slim fit” shorts or get your shorts tailored.

You want to avoid the trapezoid silhouette – where your shorts are wider at the bottom than the top. This happens when the leg opening (or circumference) or your shorts is a lot wider than the circumference of your leg.

It creates a bottom heavy silhouette, just like when women wear loose skirts. Great for them, bad for us.

Plus it makes your legs look thin and weak because they're being swallowed up by your shorts.

Instead, try to achieve a nice gentle taper that follows the line of your body:

Slim fit shorts

shirt | shorts | sandals

Your shorts don't have to be skin tight. They should be fitted and comfortable. Make sure you there's a little wiggle room between the fabric and your skin, but not more than a couple of inches.

Fit Hacks

Just like pants, shorts can be hemmed. Or, if you don't want to pay the tailor tax, you can also just roll your shorts up.

You can also get them tapered for $15-25 and have the waist adjusted by 1-2″ either way.

When trying on shorts, it's most important that they fit in the seat and crotch. Everything else can be fixed.

Styles and Details

Here's a quick list of what to avoid:

  • Cargo pockets
  • Large, bold patterns
  • Obvious branding/logos
  • Distressing (tears, rips, holes, stains)

Stick with solid colors and small scale patterns or prints. For example, if you like polka dots or floral prints, that's totally fine. Just make sure they're small in scale (small dots or flowers).

Doing It Right

Need some stylish inspiration? Here are some men of modest height wearing shorts the right way:

Josh Hutcherson shorts

Donald Glover shorts

Dave Franco shorts

Bob Marley shorts

Donalg Glover Spring Look

Nick Wooster shorts

Scott Schuman shorts

Where to Buy Shorts

UPDATE (April 2017): Tried on a few popular “mall brands” to see how they fit:

The good news is that many brands offer sub-9″ shorts these days. Choosing the right fit for your build will take some trial and error, but here's where to start:

If you're looking to revamp your shorts collection and find a new brand that's perfect for you, I recommend ordering a few pairs off this list.

Once you find something that fits, order a couple of different styles and colors, then you'll be set for a while!

What's your favorite pair of shorts? Leave a comment below!

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  1. Great article, this was my next step In achieving a better wardrobe. You definitely right about the 7″ length. Even if the man wearing them has big legs I think that is gonna look great when I go shopping for shorts.

    • Screw all of this, you all look like prep snobs trying to fit into a lifestyle that was never cool to begin with. I don’t want to see your knees. Think for yourself you sheep.

      • Want to tell us how you really feel, Jeff?

        You’re not the first person to leave an unnecessarily nasty comment on this post (who knew a post about shorts could stir up so much emotion?).

        What I don’t get is, you CHOSE to red this article. Which means you saw it somewhere and clicked the link, or you Googled “how to wear shorts”.

        Maybe it’s time to start thinking for yourself, considering the strong opinions about shorts.

        • Don Renollet says:

          damned trolls. Why do they exist? Where do they come from? More questions than answers and i don’t want to know the answers. I have adopted YOUR guide, and even tell my tailor on shorts (she calls them bermuda shorts – okay sure cool by me), i say “..just want to see my knees please” Great stuff. Took all my cargos to the salvation army, i felt….”born again”.

      • Jeff is the kind of guy that probably beats his dog or cat for no reason. He’s just an angry lonely loser…

        • I googled 15″ inseams and thought this article would tell me where to find some, being 6’5″ and prefer my shorts to sit just below the kneecap 15″ inseam works perfect but hard to find, not everyone likes shorts above their knees

          • Plenty of longer shorts out their! I’m surprised Googling 15″ inseams landed you here, actually.

            For what it’s worth, I don’t recommend wearing short that go past your knees, even at your height.

      • Wow. Those are the ugliest shorts I have ever seen! 7″ inseams? Really? They look horrible. The comment about preppy is right on. I think you must still be living in 1982 because that’s where that awful look came from.

        Those baggie shorts you panned are 10x better.

  2. Great article. Never knew if it made a difference. Jeez! It’s a struggle to be short. Might as well give up and go natural. Lol

  3. I’m definitely on the Kendrick Lamar end of the spectrum here, and I’m totes ok with that.

    Josh | The Kentucky Gent

  4. Many thanks. I am on the point of buying a new pair of shorts (retired the old ones when they became threadbare). I was well aware of length and width, but erred on the high side (9 inch inseam and the least wide I could find on the rack), but evidently that won’t do. I suspected this to be so.

  5. Peter R says:

    Pretty much every pair of shorts I’ve ever owned looks like one of the first three no-no pictures you put up in this article 🙂 Even worse, sometimes I’ve bought 3/4 length that look full length on me… ouch. The UK suddenly got hot this week (33 degrees, that’s super hot for here) and I don’t have a single pair of shorts so I’m in desperate need. I’m going to go out shopping with this article to hand and see what I can rustle up…

  6. But, what shorts work best at the gym?? Basketball shorts are way too baggy!

  7. Just what I was looking/hoping for. I’ve always had the length down right, but the width killed me with the dreaded “trapezoid silhouette” as you call it. Thanks Brock!

  8. Mike Fleck says:

    I recently found Chaps at Kohl’s and was very pleasantly surprised by the great fit and value! I bought 3 pair for the summer.

  9. One big disagreement. Don’t go shorter with the length. Nobody needs to see that much of your leg except maybe in certain athletic activities. When I see someone in short shorts, like a few of the guys in the pictures, I cringe. Doing so strikes me as either an attempt to show off, which fails, or in a related motivation, anexpression of insecurity. I like them just above the knees.

    Good article though.

    • Fair enough, I actually like them a little shorter (like 2-3 inches above the knee) but it’s personal preference. I think some guys can pull off the shorter shorts look better than others. Definitely takes some confidence or you will feel very exposed.

      • Having the legs for shorter shorts, which I think is what you mean by being able to pull off the look, is one issue. Rudeness is another. This is very much about situation. With shorts, as with tank tops, we are getting close to innapropriate exposure. Like having some guys armpits near you face or nipples nearly exposed when he is sitting arms length from you, shorts cross the line to awkward social situations easily.

        I kid you not, but this very morning I was sitting in my favorite local breakfast spot, when in walked some guy with shorts well above the knee. It wasn’t pleasant especially when he stood three feet from where I was eating. No, working out would’nt have made it better, only worse, like he was trying to make some sexy, macho statement. My appetite could have been effected.

        This effect decreases as you go more toward outdoor activities: Walking or running in the park, for instance. Also, the guy holding the microphone in the picture above is apparently some performer, so more latitude is given.

        Again, think of other people’s comfort level.

        • If you are made uncomfortable by how other people dress, then the problem lies with you rather than with them.

          • I think the problem in those situations is with people who refuse to consider customs, traditions and standards of a society. That means the guy in short shorts and a tank top bearing his hairy thighs and arm pits within a foot or two of my face. No one should have to tell an adult why that is innapropriate. Unfortunately, we have an culture now that produces perpetual adolescents who seem to think it righteous to childishly deconstruct norms. Those people are the problem, not me.

            If you really believe what you say, then try dressing in a pair of daisy dukes and a halter top next time you go for a job interview where suit and tie would be expected.

          • John, he doesn’t have a problem and neither does the person wearing the short shorts. It’s his opinion. IMO, short shorts look lame on men. They are about as lame as men wearing skin tight jeans.

          • Antonymous says:

            I might get that by customs you mean those shared by you and by which you feel integrated in the society, used as an ingroup criteria to cast out those who don’t dare polling the city before going for a style. This makes so you are grossed out by a man exibiting his leg, because you feel entitled to only see women making such fashion statement or looking good for you, so you feel not at ease and almost assaulted if what you see belongs to a man, because you know, you are not interested, so I guess you are not supposed to see it.
            I got political because you flipped out with your last reply and you got explicitely political against people not conforming to estetical norms.

          • I know I’m a year late to this party but I have no idea what “customs, traditions and standards of a society” you speak of. Perhaps it’s something you aren’t accustomed to as shorts have become longer and baggier over the years, but the custom you’re speaking of is nothing more than a fashion trend of the past 10-15 years. Personally, I am glad there’s more shorter shorts available. See you at brunch very soon.


  10. You forgot the most important inspirational pic. 😉

  11. What’s your feeling on Bonobos shorts? I think you’ve recommended them before.

    • I haven’t actually tried their shorts. Tried their pants a couple years ago, and they were way too baggy on me. I assume their shorts would be too wide for me but can’t say for sure.

      Have you tried them?

      • I have three pairs of the chino shorts. I find them to be well made and i love the colors and the options in length (i’m 5’5″ and i rock the 5″ inseam). Truth be told i find them a tad wide – i wish they tapered just a little for a slimmer fit. My legs may be on the slightly thicker side so yes if you had more slender legs, i guess i would not recommend that cut of bonobos. They have a dressier version that fit a bit slimmer on me though.

  12. Ugh, I just bought several pairs of J. Crew that are 9 inch. Can I still wear them? What should I do with them?

  13. I think there is a fine line between the right length and too short – i think childish gambino wears his too short and it just looks stupid; just above the knee is perfect. I definitely agree with the point about width though, I can never find a pair of shorts that are tailored to my leg.

  14. What size shoe do you have for the sandals because when I click on the link it says they are women shoes. Thanks!

  15. Short shorts are generally for senior citizens, gay men or young teeny boppers who have never played a sport in their lives. Shorts should go to the middle of your knee cap or slightly past. Never wear tight fitting shorts. It’s a feminine look on men.

    Inseams should be 11 – 12.5″ Again, the shorts should hit the middle of the knee or slightly past. Of course inseams may vary due to the length of the person wearing them.

  16. So what I’m getting is you are fond of short tight shorts. Like the above commenter mentioned it’s an effeminate look, personally I think Wahlberg and Cruise have a good look going in those pictures while admittedly Depp looks like he is wearing his muffin pants (or I guess shorts).

    The whole skinny tight fitting men’s clothes thing is a fad that will (hopefully) pass.

    • Big difference between “skinny tight” and clothes that fit. Shorts should NEVER go past your knees, especially if you’re a shorter man. There’s nothing effeminate about shorts (or pants) that fit.

      Sure, it takes some getting used to if you’ve been wearing baggy, oversized clothes your whole life (which was the case for me until I hit my mid-twenties and started to care).

      You’re entitled to your opinion, but I completely disagree that Wahlberg and Cruise “have a good look going” in those pictures.

  17. Mario Benavides says:

    I find American Apparel has good shorts in shorter lengths. I like the retro cords similar to old OPs.

  18. Logan Brammeier says:

    What are your thoughts on JackThreads shorts?
    They say 9″ but it kind of looks like they fit shorter in the pictures.

  19. I notice you wear birkenstocks often. What color do you think is most versatile?

    Also, how “dressy” do you consider birkenstocks to be?

    • I like dark brown, but if you have a lot of black/white/grey clothes, I’d say go with black.

      I’ve seen people try to dress them up, but I think they’re VERY casual footwear. Definitely not “dress sandals” (if there is such a thing).

  20. BoWilliams says:

    I read your article and all of my shorts were too long and too baggy. I’ve got to admit that they looked bad on me so I went shopping for casual shorts that fit my 5’6’ frame.

    I don’t like buying clothes via the Internet since I prefer to try it on before buying. As with clothing for short men, it was difficult finding the right size since most retail stores only stock the most popular inseam length: 10” or 11” inseam.

    After browsing through numerous stores, I came up an American Eagle Outfitters (AEO) retail store that had slender flex shorts with a 9” inseam. They also have similar looking shorts with 10” and 11” inseams so you’ve got to look carefully at the size tag to make sure it has a 9” inseam.

    I normally wear pants with a 30” waist, but the waist size on the AEO flex shorts run big. I ended up buying shorts with a 28” waist. .

    The flex shorts are labelled “slender”, but they’re not tight or appear to be skinny around my thighs.

    The only negative that I can give after shopping at the American Eagle Outfitters retail store is that their inventory on the 9” inseam flex shorts are limited and even more limited for waist sizes in the 28” to 30” range. I bought the last two in stock with a 28” waist size.

    At my height, the 9″ inseam length is the perfect length.

  21. Your write-up on shorts is garbage…. Who made this 1″ or 2″ above the knee rule. All of these “proper” examples of men wearing the ideal length of shorts look like a bunch of douche bags. If someone wants to wear longer shorts let them.

    • Thanks for sharing your thoughts, Jim. Much of style is subjective, but some things aren’t. Shorts that go past your knees make short men look shorter, period.

      I don’t know about you, but I don’t want to look shorter.

      But hey, feel free to write your own guide on shorts!

  22. I recently started reading your blogs and find’em godsend as i am just 160 cms. I am wondering if i can just cut my old pair of jeans slightly above the knees for the summers.

  23. Here’s a tough one for ya. I’m stuck between fashion dislikes and age related style. Even though I run and work out every day, I’m pushing 60 I bet many would rather not see me in shorts at all. I remember my first trips to Palm Springs and Florida and seeing all the old folks in short shorts with tanned, saggy, wrinkly legs, punched out knees and a tennis racket or golf clubs. That’s one extreme. The other is the typical obese little league Dad with calves the size of my waist in baggy silk basketball shorts half way down his shins to blend with the equally baggy shirt in an attempt to hide his 50″ plus beer gut, and still try to look cool and athletic. The first says “I’ve paid my dues and you can gag all you want, I’m gonna be comfy”, and the other says “don’t my kids think I look like a cool basketball star, even though running 50 yards would probably give me an M.I.”. Shorts too far above the knee at my age is reminiscent of old school when cut off Levis had the pockets hanging out the bottom and was OK, not anymore. And going too long you run the risk of looking like somebody wearing a mullet, just one of those foolish things that should never have happened. So, what’s an old dude to do? Right now the only thing that seems comfy is tapered cargo pants, but then I feel like I should be wearing a pith helmet. 😉

  24. “it’s most important that they fit in the seat and crotch. Everything else can be fixed”

    WRONG! I’m 6’3″ and really skinny so I buy these huge legged saggy butt 12″ sorts from AE and have a tailor take the seat and legs in. $15 and they fit perfect, landing just above my knee.

    It’s easy, she uncuffs the legs, cuts & resews up inner leg, recuff leg.

    • So…confirmed: “Everything else can be fixed.”

      Btw, depending on the placement of the back pockets (especially if there are two of them), having the seat taken in can really throw off the look.

      Tapering the legs, on the other hand, is easy, just like hemming.

      Also, $15 for all of that is a ridiculously low price. In any major city, you’re looking at at least $25.

  25. Thanks for the great finds!

    Just an FYI to interested buyers, I’ve had a lot of trouble with ASOS (things don’t arrive on time, if at all, and refunds are near impossible to come by, customer service is a joke). Better to look at the other sellers on this list!

  26. Thanks for the tips. What recommendations do you have r.e. short-men (I’m a bit under 5’6″) shorts and carrying a wallet & iphone & keys in (front) pockets? I’ve preferred cargo shorts because of the ease of carrying those items (safely/securely). But baggy cargo shorts have their substantial negatives.

    • I’m the same height as you and struggle a bit with finding shorts I like. I also hate wearing shorts and then stuffing them with keys, knife, pen (mini pen), and wallets (I prefer to have two super thin wallets – one in each back pocket). All of that stuff bulges the pockets and really detracts from the look. So I finally decided to start carrying a bag for all that crap. More crap in the pockets bulging out might not be noticeable if you’re 6 feet tall, but the same amount of stuff in the pockets of a shorter guy – I dont know but I think it is much more noticeable and detracts more.

    • BoWilliams says:

      I wear a FlipBelt when I run or work-out to carry my MP3 player, wallet, and keys. Since it kept everything secure and I found it comfortable to wear, I started to use it when I wore my casual shorts to carry my cellular phone and keys. Since I have a thin wallet designed for the the front pocket, that where I carry it unless I think I’m going to be pick-pocketed or it might get dropped (trains, subways, buses, or any crowded venue). In those situations, the wallet will also go in the FlipBelt (and I flip the belt to keep everything secure).

      When I use my FlipBelt, I wear it around at the belt level of the short which is the most comfortable for me. I wear my shirt tucked out so the FlipBelt is not visible. There are several different colors of FlipBelt, but a gray colored one matched my shorts and it’s a neutral color so it’s not noticeable when I have to remove anything from my FlipBelt. After awhile, I found that I could quickly and stealthily insert and remove things from my FlipBelt without anyone noticing.

      If you prefer to wear your shirts tucked in, a FlipBelt is probably not a good option.

      The FlipBelt is somewhat pricy, but it’s worth it. It’s good quality (I believe they’re made in the USA so beware of cheap and poor quality knock-offs). I’ve had mine for over a year without any rips or tears.

      • Thanks for the FlipBelt suggestion. When you wear a FlipBelt with your casual shorts, do you also wear a regular belt? Also, does your FlipBelt press against your skin at all? Sorry if these questions seem silly.

        • BoWilliams says:

          I don’t know why, but I do wear a belt with my casual shorts and FlipBelt. It’s probably out of habit, but I have no problem wearing a belt and the FlipBelt together.

          The FlipBelt does not press against my skin. The FlipBelt has no zippers or buckles so there are no pressure points that can dig into the skin. There is a FlipBelt with zippers, but I don’t think it’s necessary and zippers can break or snag and be the source of uncomfortable pressure points.

          The FlipBelt is designed and marketed for runners so security and comfort are essential. I’ve worn mine for hours and I hardly notice that I have it on. There are a number of FlipBelt reviews on YouTube.

          Before you buy one, you should consider what exactly you intend to carry. If you’ve got a thick fat wallet, a ring full of keys, an oversized cellular phone and a bunch of other things, you’d be better off with something else. If that’s the case, you’ll probably have to sacrifice fit and fashion for the function and practicality of cargo shorts.

  27. Banana Republic Aiden slim fit shorts are another option. These are about 1-2″ above the knee, are available in multiple colors, and are often on sale. They have a nice, tapered look and are very comfortable. They also have fairly deep front and back pickets for keys and wallets and can accommodate most average-width belts. And no, I don’t work for BR – I just love these shorts.

  28. I would have to disagree on shorts being tight they show the diameter of you thigh, and even so short showing a little ball sag– it ventures into the world of homo-erotic behavior. REAL GUYS, listen up & loosen up (not too much; there was extreme exaggeration in the a aforementioned pics), and dress like real men, not fairies in tights…

    • Lee, can you link to a photo of – in your opinion – a real man wearing shorts the right way? Just trying to get a feel for what you mean.

    • Antonymous says:

      Homo erotic behavior = form of erotic/romantic attraction toward the same sex. Nothing about shorts, at most I’d say bad taste, if too short :).

  29. “They should stop at the top of your kneecaps (at the longest).”

    Uhhh, I didn’t know there was a rules book on this.

    I wear my shorts halfway down my thighs. They are called “shorts” for a reason.

    This is especially true when working out in a gym where the body gets real hot, and it is summer time.

    • BoWilliams says:

      When you wear your “shorts” halfway down your thighs, they’re called Culottes or Capri Pants. If you’re a very tall and an athletic looking guy, it doesn’t look too bad. If you’re short or average height, the mid-thigh length cuts off your legs and makes you look short and stumpy. That being said, male Culottes and Capri Pants seem to be a fashion trend on the street and in the gym. H&M sell them. Old Navy sell them. Singer Chris Brown wears them. They’re popular with men in China and in some areas of Europe, but it’s an unflattering look.

  30. What’s your take on jean shorts for men? Personally like the distressed look with a hole or two for the summer months. Plain denim shorts without any ‘character’ looks conservative and unhip. They also need to fit like a slim jean. Thoughts for a relatively hip straight man on this?

  31. Thanks Brock!

  32. I would say it’s personal preference. I’m 6’5″ 240lbs and personally would not wear shorts that are above my knees. I just don’t like the look.

  33. The shorts in the pics look too short. Very conservative.

  34. I prefer regular fit with 13.5″ inseam with mine 5’10”. So almost all my shorts fits below knee.

  35. Who wears short shorts says:

    Whatever happened to real men… For those who wear their shorts well above the knee be sure to get a vasectomy! This new generation is becoming super feminine it’s pretty damn disturbing to say the least.

    • Antonymous says:

      I don’t see things deliberately “feminine”, just more fashion leeway, which used to be considered feminine. Sometimes I feel men fashion is too conventional and I say this with nothing against a nice classic blue (but well fitting) suit.
      So one aspect is:
      More fitting clothes, more details, more shared accessories between men and women. more variance in the casual-edgy area, on the neck cut of shirts.
      But as long as a given style fits the male anatomy it’s not “women clothes” more than women jeans are “men clothes”.

  36. Great article! Glad to see some solid advice being given. After high school and college you realize a little effort goes a long way when it comes to clothing. As the article says you don’t have to go aggressive with a chubbies 5.5 inch inseam but they should never dip below the knee. That being said I’m 6 ft and love wearing my chubbies and also the polo classic fit 6 inch inseam shorts are nice as well. Give me a solid tee shirt and a pair of sperrys/converse and I’m set all summer!

  37. doctor cox says:

    great introduction… on how to make a man look like a ludicrous ittle boy. “awww, now what a cutie pie…!”

    anything clearly above or below the kneecap looks nothing but ridiculous. you disagree? how can i get it across to you politely… – well, you’re wrong.

    • Thanks for your thoughtful comment, Doctor Cox.

      Just curious, what did you Google to find this article? Was it “how to wear shorts”?

      • Antonymous says:

        Don’t you love how it all is so reminescent of when women gave scandal for wearing something just above the knee?
        We arrived to this day to read of people scandalized of men wearing shorts which fit and just above their knee?
        Isn’t it restricting if you think about it? Some people seriously think they are defending “masculinity” with more restrictions??
        Nice tips btw.

    • Don Renollet says:

      Dr. Cox, just like the British WWI 8th Army division

  38. Frederick Mwangi says:

    Although pricier, you forgot Bonobos Brock! Their shorts fit amazingly off the rack. They come in 5, 7, and 9 inch. The fit is very close to body without being too tight. I’m 5’6″, went with their 7 inch, and love the fit. Thanks for the article, it really helped me nail down the shorts I needed to get in order to look stylish as a modest man ;/

    • Good to know! I’ll have to try them out. Their chinos were too loose for my legs, but I haven’t tried their shorts yet. Thanks for the tip.

    • I have some of their golf pants and they’re the first I pull out of the closet. Bonobos make good clothes.

  39. Bill Lawrence says:

    Not sure if i would wear them above the knee thats an old farts way to wear shorts in my opinion. It was popular in the 60s 70s and 80s but not nowadays.

  40. BoWilliams says:

    This week, The Wall Street Journal published an interesting article on men’s cargo shorts. Who knew cargo shorts could generate so much debate?

  41. Bill, I’m deleting your comment because it’s immature and offensive. Just wanted to let you know.

  42. I guess everyone’s got their own idea or what they like and feel comfortable with,so what suited me is not necessarily for others. Aside from sports I only ever wore shorts to stay cool (temperature-wise that is) and to get a bit of tan (without tan lines) so I wasn’t greatly fussed about how I looked. I never liked or saw the point of below-kneecap ones,might as well stick to trousers or jeans then. I don’t like baggy ones either,I think they tend to make a lot of people look fat or maybe that’s just the people I saw wearing them. I used to really like wearing shorts in the warmer summer months,I went from the 70s through the 80s and 90s and up to 2001 wearing them as much as I could,but after that I decided it was time to stop (outside the boundaries of my house and garden). My age and weight 🙁

    Shorts in the 70s,80s and to some extent the 90s were certainly shorter,so that wasn’t seen as unusual by most people back then. I used to wear them short to very short without getting any aggravation at all,just a little teasing now and then (as much from the opposite sex really). A couple of my female friends thought it funny to sit either side of me an take turns slapping my legs,when we were all sitting out together on the grass and even in the pub we used to go to a lot,and one of my girlfriends was burning the threads off my cut-short jeans with her lighter when we were out in this bar in North London. Fortunately my long legs had the shape,curve and tone to them for me to get away with it (playing a bit of tennis was good for that). The longest ones I ever wore were just above the knee but for the most part I wore one that were mid-thigh (often cut-short jeans) but some that were upper thigh and a few were very short – yes really! I wore them mostly with T-shirts,sometimes with sweatshirt type tops,and with trainers. I had quite a number of denim ones through those years. The shortest pair I ever wore was in my teens,that was a pair of jeans a girl friend I was at school with cut so short that they were inadvisable to bend over in! I got a bit of ribbing for wearing those for the first couple of days but it seemed to die down after that; I only wore them on the really hot days in one summer,most often when on my way to and from going swimming. I used to have a photo someone took of me wearing those and an orange T-shirt with a sketch of a lion on it,standing in the doorway to some gardens on a blazing hot day at the tail end of the 70s,but I haven’t been able to find that picture for some time now.

    But no way would I even think about wearing shorts to a job interview (you mean there are people who do?!?) or any occasion where I needed to dress smartly,including office jobs (though at one place I did at least a couple of times in hot weather when doing Saturday overtime with the office reception closed to customers). And I wouldn’t wear them once past the mid-30s or if becoming more than a tiny bit overweight – but it’s amazing the number of people waddling around out there who do. I can only think they’re compensating for feeling repressed or compelled not to wear them in younger years.

  43. I miss being able to go out in my shorts,though. The farthest I venture out in them is a spot nearby where I can bash my tennis ball about for a couple hours trying to get properly fit again and keep in shape. I only see a people there and most of them I know already. I’ve still got one pair of cut-off jeans ones I usually wear for that; I just tried putting them on and measuring them and they’re about six to seven inches above the top of my kneecaps (but I’ve got quite long legs). I did wear them out several times in the summers of 2011 and 2012,the latter time I was staying with relatives recuperating on doctor’s advice from a heart “event” I had from overdoing it and burning the candle at both ends,and they would take me out on day trips to a few places. I also do 15-mile walks with some bursts of running in the countryside and I’d really like to wear them for that but it means walking through the town and I’m not up for that any more -too many years on the clock and still too many pounds round the waist,although I’ve lost a stone over the summer through exercise and some healthy eating (NOT dieting).

    I think my post post could give a couple of wrong impressions,though,like it’s a bit “too much information”,I don;t know can I edit it a little on these pages. The ones that I said were inadvisable to bend over in were likes the daisy dukes that girls wear but they did at least cover my ass cheeks – just!

  44. Here’s my pet peeve. I can’t find a decent work short with a cell phone pocket in a 8″ inseam. The Carhartts are great shorts, but so baggy that a slim guy like me is swimming in them. Bonobos washed chino shorts fit well, but no cell phone pocket, and not durable enough for work. I wish some of the old school workwear companies (Carhartt, Dickies, Wrangler, etc…) would get on the bandwagon.

  45. Howdy. I have quite pronounced surgery scars on one knee so I like my shorts just over my knee rather then 2 inches above.

    The trouble I have found is that being 6 foot 4 I either find shorts that are too high…like 4 inches above the knee, or too low…ie 3/4 length which I hate.

    So I had a pair of shorts exactly the right length and decided to pick out some nice Mossimo jeans and have them cut into shorts by a Tailor.

    Trouble is the Tailor did’nt place the shorts on top of the jeans and mark accordingly but measured from the inside seam…ie….from the crutch to the bottom of shorts. The shorts had a longer crutch then the Jeans which meant that I ended up with 3 pair of Mossimo jeans all cut to the wrong length. …ie…..3 inches above the knee rather then just on it.

    3 Pairs of Mossimo Jeans ruined for no good reason and 50 bucks worth of Tailoring on top of it.

    The Tailor refused to admitt any mistake saying all Tailors measure from the inside seam not the entire short length. What the???????

    Anyway, sounds as though the shorts are the Perfect length for you….wanna buy them??? 🙂 🙂

  46. Just want to thank everyone part of this discussion; making my decision all the easier to burn all my shorts and lean on my linen pants for my holiday travel. I’ve always known that the shorts “debate” is a contentious one, and I’ll admit, they’ve never really sat right on me too, and every time I’m about to head to a warmer climate, I Google shorts related topics for a brush up and every time I come out of it thinking that men just shouldn’t wear shorts at all. Irony is, I look and feel great in my swimming trunks, which are quite short and fitted; probably several inchs (mid-thigh) above the knee. Like the Marley photo above. But then again, they are strictly worn at the pool, in the Haman/Sauna, and at the beach, where in all three places, anything below mid-thigh is not only unsightly, but unsanitary. As for “shorts”, the chino variety, yeah, no, I’m sending those off to goodwill. Something confusing happens when you mix the casualness of a short and a chino material, which I may add, looks tired after a couple washes. I’m 5’9 and very fit for reference and you’d think the ideal candidate for shorts and even I think they generally look terrible on me. Funny enough, I think shorts look their coolest when they are kind of metal, like the guys I watch on the car shows with the tattoos and they are loose fitting and slightly below the knee (always black) with a utility pocket on this side. That’s just not for me however, and it’s probably the only time, I’m like, you know, those shorts look pretty bad ass. I tend to agree with many on here, shorts can quickly look boyish or dainty. And now, while I usually the first to say things look better on taller men (than my 5’9″ frame), I can universally say that shorts look good on know one.

  47. I just came across this article to find some good tips for wearing shorts for short men. At 5’7″ I never really liked wearing shorts because most of the men’s shorts are either cargo, bermuda, or gym/basketball shorts. I did own a pair of cargo shorts, but they are long gone from my wardrobe. Not only I do not like the designs, but they just look so baggy and long on me. Now that I’ve found more shorter shorts like Chubbies, I can finally find actual shorts that I actually like and don’t go below my knees. They don’t look that short on me. I rock them out occasionally when I go out. I am now encouraged to work on my quads and maybe get a girl (or two). With that said, I don’t follow fashion trends I wear what I feel more comfortable in and people should do likewise. If you like cargo shorts, by all means wear them. Not me. I like these shorter shorts on me,

  48. Really surprised by the notion that mens legs aren’t to be shown. I just started wearing shorts again this past year, As I grew more comfortable with my appearance, cycling and getting tan again, I went shorter and shorter. I have quite a few pair of running shorts and wear them just about everywhere I can. Maybe the 2″ inseam is a bit short for some people but I’m not here to suit others fashion taste. I dress to be comfortable and if you don’t like what you see, turn your gaze elsewhere, especially if you’re a guy checking me out. As long as everything is covered, and it is in my case, why worry about what someone else wears. Reading the comments here goes with what I experience on the street, men are bothered way more than they should be by what other men wear. Of the comments I get, 10 to 1 it’s from a guy. I know at least some women like what they see, thankfully some even threw a compliment my way. Funny how a woman can have half her butt cheek hanging out and nobody says a word. A guy wears short running shorts and the world stops turning. Another thing I noticed is the overwhelming majority of responses here seem to be from other guys. What do the ladies think about the subject? I’m well aware that women look, sometimes smile, wink, nod of approval given. I’m wearing my short shorts. If you like your shorts longer, go for it. Personally, I’ve never found shorts at knee length or longer, to look good on anyone, male or female. I don’t feel it’s my business to tell anyone else what they should or shouldn’t wear though. To each their own.

    • Antonymous says:

      I really agree, what problem do these people have? I personally prefer them not too much above the knee and with a pair of good sandals, but more power if other people prefer or can pull them off higher!.

  49. I have always felt that to be called “shorts” they needed to be above the knee. I have spent many years refusing to wear “longs” – the length is uncomfortable and I always thought the looked stupid – kinda the same look as the waist band of pants being around your thighs instead of your waist, but I digress.

    Now that time has passed and real shorts are making their way back, I was going to order some, but my health got in the way. I have deep vein insufficiency and have to wear waist length compression hosiery. What’s a guy like me to do when it’s 100 degrees? I’m pretty laid back about what people wear and have never been bothered about what I wear as long as it’s comfortable. HOWEVER, male+pantyhose is just a really, really bad look in my opinion.

  50. Hey Brock,
    I’m 72, 5’6″, 150lbs. and live in Florida where shorts are worn all year. What brand do you recommend that’s age appropriate (not baggy, not tight, not too short). Thanks.

  51. toolarmysniper says:

    Google Image douchebag shorts. The only reason I got to this site is because I’m trying to find a size chart so I don’t get shorts like them.

  52. Teddy Sall says:

    wow all those people in short shorts look TERRIBLE! They need to be at least to the knee, anything shorter looks ugly as sin

    • Came here to say that?

      • Not sure what the difference is between male and female legs in general, but if Mancapris are your style, more power to ya! For me, shorts at or below the knee are like a “short sleeve” shirt where the sleeve hits below your elbow. Not only is that length annoying, it just doesn’t look good. Ill-fitting would be my initial reaction.

  53. Hey Brock! Have you tried hemming your slim pants to shorts? Thinking of getting my 29×30 chino pants hemmed into 29×7 shorts. Is the cost the same as a simple pants hemming? What would it look like?

  54. Looking for some advice on wearing crew height socks with shorts. I liked what you said in the GQ myth article about how obsessed people are with bare ankles these days. I think socks can be a simple way to add some personality (mind you, I equally dislike novelty/overly bold socks).

    Still, I feel like I never see anyone wearing anything but no show socks with shorts these days. (Besides athletic attire – thanks to Nike) I’m not trying to look like a skater or anything but I’m wondering what your thoughts are. I have a bunch of Stance socks – not the bold/obnoxious ones – but dark hues with a simple strike or color block pattern but I’ve been too self-conscious to wear them with shorts because nobody seems to give advice about it. Is it that bad of a thing to do?

  55. I have the same problems with shorts as you, and like you, the American Eagle Slims fit me best. But I went to Kohls today and discovered some cheaper shorts I think you’ll like. Sonoma Flex Fits. Perfect for my body type.
    Thanks for the informative video!

  56. The Izod Saltwater Stretch Shorts fit nice too. 32″ waist with 10″ inseam. $26.99 at Kohl’s.

  57. C. V. Charles. says:

    5 inch is the max inseam length for shorts. I like running shorts with their 2 or 3 inch inseam. and a loose but not floppy fit.

  58. asbrocca4 says:

    Very nice, thanks

  59. I found a pair of shorts that I have worn for about 6 years & as you can imagine are needing replacement. Trouble is that Old Navy never carried them after the one season. I look every year with disappointment.

    One thing that might be a whole post worthy is how to find out enough about an item to locate & purchase it (again). I have googled every part of the tag on these shorts with no luck. Other times I’ll find a great pair at a thrift store & either want more, replacement or different colors or sizes. Occasionally I’ll even ask a guy where he got his (after paying a compliment of course 🙂 & rarely can get more than brand for the same reasons I’m having difficulty. Your insight & expertise is welcome.

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