A Gentleman’s Guide to Wearing Shorts

Summer is here, and she’s roasting much of the country. In these hot and sweaty times, shorts are certainly an appropriate garment choice for men. Unfortunately, there are still a few men that ruin it for everyone with their poor definition of style and keep the stigma of shorts being “too casual for gentlemen” alive. These are nearly always the same men that ruined sandals by wearing bright white ankle socks with them.

gentleman's guide to wearing shortsDamn it, Jerry. Jean shorts, socks and sandals, and
my God man – are those BluBlockers? We’re no longer friends.

Don’t worry, there are a few key principles to follow so you don’t end up looking like Jerry*. Recently, there have been a lot of articles on what kind of shorts for men are appropriate. In these articles, there have been some good pieces of advice, but also some terrible faux pas that were declared “ok” from now on. I call bullshit on two main points: cost and cutoffs. Let’s review The Sharp Gentleman’s guide to wearing shorts like a man.

*If your name is Jerry, I truly don’t mean to offend you. It was simply a random name that popped into my head when writing this.

When can you wear shorts?

This is actually a great, basic question. Recently, there’s been a new trend in which a full suit is finished with shorts instead of proper trousers. This trend is not appropriate for a modern gentleman. If you happen to be a performer or celebutante attending an MTV gala, you’re more than welcome to wear whatever you like, including a suit with shorts. You, however, are not Pharrell Williams, so you’re not allowed to wear this getup. Feel free to browse google images to discover other men trying the look… and failing miserably. Trust me, I’m do this for your own good.

1 – When the location, event, or temperature are appropriate and

2 – When you are purposely dressed casually (not conducting business or attending a formal event)

The main key to remember here is the idea of shorts being appropriate when the situation is also appropriate. This is why I put “and” instead of “or” between those two points above. Let’s look at an example. I’ll describe a situation and as we go through it, I’ll put yes or no in parentheses to tell you whether it’s a-okay to wear your short pants. Watch out – it can get tricky.

You’re at an outdoor summer (yes) wedding (NO). You’re on vacation in Key West (yes) and you get invited to have dinner on the beach and talk business with another executive in your industry (no). You’re golfing in July (yes, but keep reading for Do’s and Don’ts).

The Do’s and Don’ts of wearing shorts

DON’T: Wear Jean Shorts a.k.a. Jorts – These are never appropriate. A recent GQ article said they were cool to wear again. Lies. The sure-fire fastest way to look like a dad on vacation at Disneyland is to throw on a pair of jean shorts. The fastest way to look like a Joe Dirt, Kentucky version of that same dad is to cut your regular jeans into shorts. Not a good idea. Ever.

gentleman's guide to wearing shortsDO: wear a flat-front, tailored pair – This could also be titled, don’t wear pleated shorts. Pleats have been out of style for several years now, and are only beginning to experience a re-emergence. Pleats aren’t inherently evil, but designers took them to extremes in the 90s by producing trousers with a dozen pleats, and even putting pleats on casual denim – as made famous by Mario Lopez a.k.a. A.C. Slater on Saved by the Bell.

Today’s modern gent needs to embrace a short (and trouser) with a flat-front. These will look slimmer and provide a cleaner, crisper look than a pleated version. The shorts also need to be a tailored fit. Essentially, you want your shorts to fit your waist and hips like dress trousers, but cut off at or near the knee. Shorts that wear baggy (too big in the hip and thigh) often make you look younger (not in a good way) than you’d like, and give you that chicken leg look.

DON’T: have strings or giant pockets – Cargo shorts aren’t necessarily off-limits, but there’s a simple equation you should know about. The further away from 20 you are in age, the smaller the cargo pockets must be. That way, you’ll have no cargo pockets left in your 40s. Avoid shorts that have tassels or strings that hang off the zippers. Carpenter shorts are off limits, however. Unless you’re a carpenter and actually use that loop for your hammer, you don’t need to clutter your legs with unnecessary pockets, loops, and rivets. Clean is king. Also, for the record, avoid the pants that zip into shorts unless you’re camping or hiking the Oregon trail. Actually, skip that trail. You’ll only end up with Dysentery and die.

DO: Show a little more leg – This is all personal preference, I know, but showing a little more leg won’t actually hurt you. The image at the right (click to expand) is an excellent guide to inseam length. I sell shorts that come in two lengths: 9.5″ Tailored fit and 8″ Euro fit. They’ll sit just above the knee on most men, and show a little more leg on some. While the 5″ inseam is a little too short for my personal taste, the shorts I wore in in high school were at least 4″ PAST my knees. Oh how young and silly we were in the 90s, right?

DO: Embrace more color than simple khaki – The world is a pretty colorful place, right? Why would you want such a monochromatic wardrobe below-the-waist? Men across the planet are really divided into three categories: those that have colorful wardrobes, those that have two bland colored shorts, and those that wear jorts and cutoffs… a group we will not discuss. Heathens. You want to be in the first group. It’s good for you. Embrace more color and patterns – they’re not just for golfers and WASPs anymore.

DON’T: Wear gym shorts or board shorts where they don’t belong – The big exception here is Californians. They wear board shorts everywhere. Then again, they call everyone “brah” and it’s acceptable, so they have their own rules altogether. Athletic nylon shorts are acceptable in the gym and when you’re being athletic, but shouldn’t be worn in other situations. Board shorts or swim trunks are in the same category. Unless you’re on vacation at the pool or large body of water, a classic chino short is a better choice.

gentleman's guide to wearing shortsWhile we’re on the topic of athletic and swim shorts, let’s talk about length for a moment. Gym shorts shouldn’t drape more than an inch past the knee if they’re basketball shorts (because that’s how basketball shorts are these days thanks to the 1990s). If your athletic shorts sit at mid calf, you’re either wearing them incorrectly (read: hanging off your backside, revealing your underwear) or you made a poor choice in style. Don’t be that guy. Other athletic shorts will sit at or just slightly above the knee. Running shorts are significantly shorter to allow for more skin to be exposed for cooling. Trust me, run 10 miles in basketball shorts and you’ll vow to run in your boxers before you do that again. Swim trucks and board shorts usually sit above the knee, but can be as short as you and your body are comfortable wearing.

Additional Considerations

Now that you’ve got your short game cleaned up, you have another task to tackle – footwear. This is actually a pretty easy one to answer for most men. You need three shoes to go with your shorts:

Get a pair of boat shoes in a brown/tan color and canvas shoes that are lighter. Once you’ve got some combinations to play with, add color in your shirt and short choices and have the best-looking summer ever. Finally, my last tip when reviewing other articles out there on wearing shorts is to be cognizant of the brand suggestions they make. There’s no reason to spend $300 on a pair of shorts because a trendy article told you to. You don’t have to spend a ton of money to look like a million bucks. Keep you head on straight, and you’ll find fashion and savings along the way. There are resources everywhere to help you embrace better fashion, so don’t hesitate to reach out if you’d like some help.

What are your thoughts on a Modern Gentleman wearing shorts?
What is YOUR favorite color or style? Let’s connect in the comments below!

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The Author

Blake Hammerton

Blake Hammerton

Blake Hammerton is the founder and coach at The Sharp Gentleman, and helps men earn more respect while gaining confidence in who they are. He is a certified relationship coach and loves writing about men's fashion, style, character-building, relationships, travel, adventure, and more.