How To Wear Shorts With Style | ULTIMATE Man’s Guide

When it comes to the question of how to wear shorts, most men just don’t get it. 50% of guys avoid shorts like the plague and the other 50% end up wearing shorts that really don’t suit them.

It is perfectly possible to wear shorts and look stylish – if you follow a few basic rules. In this article, we’ll show you how to wear shorts with style.

In this article, you’ll find:

1. History of men’s shorts
2. When to (and when not to) wear shorts
3. How to wear shorts that fit
4. The right length for men’s shorts
5. Choosing the right fabric for men’s shorts
6. How to choose the right color for your shorts
7. Different types of men’s shorts
8. What clothing to wear with shorts

#1 History Of Men’s Shorts

Shorts started as ‘knee pants’ for boys in the 1890s and served as the basis for school and scout uniforms. Roughhousing and tripping over would mean torn knees if a boy wore full-length trousers. When a boy reached maturity, he was expected to stop wearing shorts and transition into wearing trousers.

This changed in World War II. Troops in tropical climates started wearing shorts to cope with the heat. They are famously shown in depictions of the British Eighth Army in North Africa from 1940 to 1943, also known as the ‘Desert Rats’. The German Afrikakorps, Italian army and Free French forces also wore shorts on the battlefield.

When men returned to civilian life after the war it was only a matter of time before shorts were normalized. By the 1950s, shorts were acceptable in casual situations in hot climates with masculine icons of the time like John Wayne taking advantage of the new trend.

#2 What Are The Types Of Shorts For Men?

There are plenty of men’s shorts styles to choose from. Let’s do a quick rundown of the key types you can find in stores.

• Running shorts are designed to facilitate the most freedom of movement during exercise. Most running shorts include an inner lining that doubles as underwear. Most are made with polyester.
• Swimming shorts (swimming trunks) – The best men’s swim shorts are made with nylon along with a mesh inner lining to dry quicker.
• Denim shorts came into style during the late 1960s as part of the counter-cultural movement. I do not recommend denim shorts as they look sloppy – like you just sheered off your jeans at the knees.
• Flat-front shorts are the most common style of shorts. The material lies flat near the zipper for a slim, low-waisted look.
• Pleated shorts feature creases where material is folded and sewn before getting attached to the front of the waistband.

• Cycling shorts are skintight shorts designed to reduce wind resistance and friction.
• Boardshorts are long, loose-fitting swimming shorts with an opening at the front as opposed to an elastic waistband.
• Cargo shorts are loosely cut with large pockets on either side. They don’t look well on most men due to the bulging appearance of the pockets.
• Madras shorts are made with a lightweight fabric and are known for their vivid, brightly-colored patterns. The style takes its name from its home city in India – now named Chennai.
• Bermuda shorts – During a WWII clothing shortage, the managers of Bermuda’s two major banks hired a tailor to make shorts based on those worn by the armed forces. Bermuda shorts have been worn with a blazer in certain cultures ever since.

#2 When Should Men Wear Shorts?

Shorts are casual garments and a staple of warm-weather clothing for men. They are appropriate for summer events when you want to be free to move and comfortable to avoid sweating in the heat.

Lounging with friends? Walking around town in the daytime? Going to a private party? You’ll do fine in a well-fitted pair of shorts.

When to avoid shorts

Some casual workspaces do allow shorts. You might even get away with wearing them to casual business meetings though it isn’t the norm in most parts of the world.

It’s important to judge the situation correctly. Look at how those around you are dressed, identify the unspoken dress code and decide for yourself if you should wear shorts.

Any situation requiring business-casual wear will require trousers. Law firms, corporate offices and banks are a few examples where shorts should not be worn. Instead, wear chino trousers or dress slacks.

The golden rule is if you aren’t sure if you can wear shorts, then you shouldn’t wear them. Opt for trousers in any of these situations.

#3 How To Wear Shorts That Fit?

How are shorts supposed to look when you wear them? It’s easy to get confused by all the conflicting info on the web.

Fit is king when it comes to menswear. Let’s discuss the best fit for different body types.

Athletic Builds – Shorts for men with big thighs

Athletic men have broad shoulders that taper down to the waist. Such gentlemen have the widest range of choices when it comes to wearing shorts.

Men with muscular bodies tend to assume that loose shorts will balance the torso. It won’t, it will simply make you look disproportional.

Opt for a tailored fit that strikes a solid middle ground. You want shorts you can move comfortably in but won’t flap like a skirt.

If bulk is a concern, then consider a lighter color – these balance the body out more effectively.

Slim Builds – Shorts for men with skinny legs

Men with slim bodies are complemented best by slim-fitting shorts. Avoid baggy shorts as they will make your torso and legs seem disproportionate.

You also want to take precautions against flaring. Your shorts should go straight down without having excess material around the edges. Again, this will make for a ‘skirt effect’ if ignored.

Dad Bods – Shorts for men with average builds

Men carrying a little more weight around the midsection need to avoid slim-fitting shorts. Slim shorts will only emphasize your stomach.

Wear shorts that are slightly wider. Opt for straight-legged shorts. They’ll improve your silhouette and minimize the focus on the waist.

Pleated shorts should be avoided. Although rare, pleated shorts create lines leading right to your waist.

Never wear shorts that fall below the knees because longer shorts (like Bermuda shorts or boardshorts) will make your legs look smaller and your stomach bigger.

Avoid elastic waistbands in casual situations. It will pinch around the waist and make a muffin top. Using elastic waistbands with swimming trunks or exercising shorts, however, is fine.

#4 How Long Should Men’s Shorts Be?

The most common lengths for men’s shorts are 3, 5, 7 and 9 inches measured through the inseam.

Short-shorts (3-5 inches) usually include athletic variants like swimming trunks and running shorts. Longer shorts (7-9 inches) comprise common styles like flat-front khakis, pleated shorts, Bermuda shorts, and Madras shorts.

Longer shorts have a more formal look than shorter shorts.

How are men’s shorts supposed to fit?

The easy answer to wearing shorts correctly is this: never below the knee. Anything beyond that ambles dangerously into jorts territory, and that is never stylish.

It also defeats the purpose of wearing shorts. If the goal is comfort and flexibility, why would you restrict the knees?

The more specific answer depends on the occasion. Go 2-3 above the knee if you are wearing casual shorts with a t-shirt, button-down, or polo. This works well with chino shorts or khakis. Athletic shorts on the other hand can easily end 5-6 inches above the knee.

How should shorts for short guys fit?

Men who are 5’7 or below are considered short in the United States. In the image above we see a 5’2 man wearing a 7-inch inseam. Notice how the shorts travel precariously past the knees.

He wants to avoid shorts that have a 9 or even 7-inch inseam because it will make his legs look short. Instead, he should purchase casual shorts with a 5-inch inseam and swimming trunks with a 3-inch inseam.

Shorter guys should also avoid cargo shorts. Huge side pockets will dwarf an already small frame.

How should shorts for the average man fit?

The average height for men in the United States is 5’8 to 5’10. A 7-inch inseam will work well if the goal is to wear a polo and loafers with the shorts.

How should shorts for tall men fit?

Tall men like in the infographic above are taller than 6’1. They run into the problem of showing too much leg. If you’re in great shape, this isn’t a big deal. Just remember that the more skin you show, the more casual the shorts will look.

If tall men want to wear a casual button-down, a polo, or loafers, then a 7-inch inseam is the shortest they should allow. When it comes to swimming trunks or exercise shorts, 5 inches should work fine.

#5 Choosing The Right Fabric For Men’s Shorts

What’s the coolest fabric to wear in hot weather? It’s the question every man wants an answer to. Let’s take a look at the most common cooling fabrics shorts are made of.

Men’s cotton shorts

About 90% of all shorts are made of cotton, with cotton twill fabric being the most common weave.  Twill weaves are dense but durable. The lack of breathability is offset by the shorts themselves which let air travel up the legs. What are your other cotton options?

• Seersucker is a three-dimensional weave that uses a puckered texture to facilitate airflow. It saw use throughout the 19th century for workwear, but it was in 1909 in tailor Joseph Haspel started making suits out of it. Seersucker also adds texture to your ensemble. It’s a great way to bring in a unique style few men will have.
• Madras is finely-textured cotton that makes use of bold checks and stripes. It began as the mainstay fabric of the Indian peasant class. Dutch and British traders fell in love with the stuff during the 1600s. Cotton plaid Madras reached America by 1718 and took off for its breathability. The problem arises with durability. Madras is prone to damage after a few years of continuous wear.
• Chambray can be thought of as ‘denim-lite’. It is the airy alternative to jeans but with an even crisper look. I recommend Chambray over traditional denim when it comes to shorts.

Men’s linen shorts

Linen is a durable fabric that is superb for summer wear. Wearing linen shorts will guarantee maximum breathability.

However, linen is prone to wrinkling. You can mitigate wrinkling by going with a tighter weave linen fabric, but you need to accept a few subtle wrinkles nonetheless.

Men’s wool shorts

You can also get shorts with tropical weight wool – the lightweight woven wool that is sometimes used in warm weather suits.

Wool is a luxury fabric in menswear and is rare in men’s shorts. It requires upkeep. You have to treat them as you would wool trousers.

Use a clothes brush on them regularly in order to remove any excess dirt or food particles. Make sure to hang them up after each wear. If necessary, use a steamer to work out any creases that worked themselves into the fabric.

Despite this, wool is an excellent choice for summer wear because it absorbs moisture better than many fabrics, keeping you feeling dry throughout the day. It also enhances your elegance in casual situations.

Men’s synthetic fabric shorts

Also known as technical fabrics, synthetic fabrics like polyester and nylon are going to serve you best when it comes to sports and exercise.

The advantage of synthetic fabric shorts is durability and low cost. They are less breathable though. However, you can find lighter weaves to compensate for this. Polyester is also excellent for repelling moisture and staying dry so maintaining these shorts is a breeze.

Uses of blended fabrics

Blended fabrics are made when at least two fibers are mixed together to create a new fabric with specific properties.

Are fabric blend shorts right for you? It depends on the purpose. One good example is cotton blended with spandex to give you more flexibility. However, blends made for the sake of cost-efficiency are usually poor quality.

Choose carefully. It may be simpler to decide between shorts with all-natural or synthetic fabric.

#6 Men’s Shorts: Understanding Colors And Patterns

Best colors for shorts

• Blue ranges from navy all the way to light blue. It’s a highly interchangeable color that goes well with the heat. Pairing navy chino shorts with a white casual button-down for example is a classic combination.
• Brown shorts are commonly found as khakis. It’s a timeless, simple color with considerable versatility. Khakis are even the common choice for slightly more formal situations.
• Gray is a noncolor that matches anything you could muster. You also have your pick of shades ranging from charcoal to light gray.
• Pastel colors such as lime, lavender, mint, and salmon are considered ultra-casual. They are highly versatile but draw more attention than their conservative counterparts above.

Make sure you have a solid foundation when it comes to blues, grays, and browns before delving into brighter colors.

Best patterns for shorts

With men’s shorts (and any clothing), extra visual detail will limit your ability to match patterns in clothes. They can add some flair when paired correctly, but proceed with caution.

• Solid shorts are the most common. No patterns mean that you can afford to get a more aggressive pattern on your chosen shirt, or even opt for busier shoes like tassel loafers.
• Stripes are sold in a wide range of sizes and color combinations. Seersucker weaves traditionally come with thin, alternating stripes known by different names depending on the time period and occupation of the wearer. In the old west, for example, a navy blue striped seersucker was called Hickory Stripe.
• Checks are a pattern of stripes that cross horizontally and vertically to form a square. They range wildly in density. You can easily find shorts bearing classic checked patterns such as Windowpane and Prince of Wales.

#8 What Can You Pair With Men’s Shorts?

Men’s shoes to wear with shorts

There are plenty of options out there depending on your preferred style. Considering how casual men’s shorts are, most dress shoes and dress boots are out.

• However, men’s loafers are classic, elegant summer shoes that you can pull off with ease. Men’s loafers are tried-and-true against the heat. They leave the ankle completely exposed which allows for better cooling. They are reliable for men seeking to enforce a more elegant air. Loafers offer a wealth of options as well – from streamlined penny loafers to the more casual tassel loafers. You can also opt for perforated leather to assist air circulation.
• Boat shoes are another option. They are simple, flat leather shoes with rubber soles designed to maintain traction on boat decks.
• Men’s dress sneakers are acceptable. White sneakers are preferable but are prone to tarnish.

What kind of socks can you wear with shorts?

Can you wear socks with men’s shorts? Of course, just stick with liner, ankle, or no-show socks.

Rely on no-show socks if you’re wearing loafers. You’re still going to need socks to keep the moisture in your feet from ruining the shoe. Don’t worry – the socks will not extend beyond the loafer’s upper. Your ankles can breathe safely.

Ankle socks should work well enough if you’re wearing sneakers.

Click here to discover how you can tell quality socks to pair with your quality shorts and shoes.

What shirts should men wear with shorts?

The kind of shirt you wear depends largely on the shorts. Athletic shorts will warrant an athletic top of a similar make.

Longer shorts of cotton, linen, or wool can easily be paired with plain t-shirts or casual button-downs. You can also sport a polo for a more formal feeling. Make sure to combine shirts with a belt if you tuck them in.

Is it OK to wear a jacket with shorts?

Pairing jackets and shorts can be tough. You don’t want to layer up if your goal is to stay cool of course. However, hoodies and athletic jackets can work well if your goal is to run or hit the gym.

You can also make effective pairings using light jackets. Consider a bomber jacket in suede if your goal is to go about the town. You can even wear a blazer with Bermuda shorts. The lighter the color, the better.

In some cultures, you can even pull off a blazer with long Bermuda shorts. As always, make sure to identify the unspoken dress code!

How To Wear Shorts – The Ultimate Guide Wrap-Up

Men’s shorts have a place in every man’s closet. As long as you understand proper fit and setting, you can turn them into a potent weapon in your arsenal.

With this basic guide, you have the knowledge to go out there and rule the summer. But don’t stop there! Click here to discover my guide to the best shoes to wear with shorts this summer.

Click below to watch the video – The Ultimate Guide To Men’s Shorts