Skip to Content

What Shorts are in Style for Guys?

The sun gets hotter, and we begin to wear less clothes. While summer brings many good things your way, shorts may not be one of them. Check out this article to find out about all the trending men's shorts and which ones are right for you.

This is a close look at a man wearing a pair of khaki shorts at the beach.

When summertime hits, people start wearing fewer clothes to beat the heat. As the weather heats up, shorts make an appearance, along with the legs that are wearing them. For many years, I was not a fan of men’s shorts, but it was probably more because of the short styles that were in fashion.

We are all thankful that times have changed, and there are many new men’s fashion styles. Continue reading to find out what shorts are in style for guys. 

What is the Perfect Fit for Shorts?

A close look at a man wearing a pair of printed short shorts at the beach.

There was a time when shorts for men were really short, but thankfully, over time, they got longer. Now, it seems that the current style is moving closer to the shorter side. The event to which you are wearing your shorts may dictate which shorts you should wear.

The best length for shorts is one where the shorts hit the bottom of your thigh. This fit will flatter all body types without cutting off your knees. You could consider a pair of shorts with a cuff because it helps to make the shorts seem shorter without showing off too much skin. 

If you have bigger thighs, you want to consider shorts that have a minimal taper at the knee. You do not want the side edges of your shorts to move out beyond your hips. This creates a box look that makes your calves seem smaller. The same concern applies to shorts with cargo pocket

Shorts Styles for Guys

Cargo Shorts

A man wearing a pair of long blue cargo shorts with his sneakers.

Cargo shorts have been around for many years. However, when they rose to popularity, they looked wrinkled, messy, and paired with an ugly t-shirt. Cargo shorts were reserved for the lazy.

Thankfully, times have changed, and cargo shorts also have. The changes that have been made to cargo shorts include a more streamlined pair of shorts with slim pockets. They no longer have the worn finish to them that made them look sloppy.

When you match cargo shorts with a clean, stylish white sneaker, you will be the most stylish one at the event. 

Sport Shorts – Retro Style

A close look at two men wearing basketball uniforms.

If you are beginning to notice that sport shorts have taken on a more retro look, it is because they are rising in popularity. The latest designers have taken a page out of the archives and vintage stores to bring backside stripes, curved hems, and side stripes on their shorts. You want to match these shorts with a nice oversized t-shirt and old-school sneakers.

Even though these are gym shorts, you want to stay away from sweatbands. Button-down shirts are not a good look to pair with these shorts. With the advances in clothes, you can take your athletic short outside of the gym.

You can match your designer athletic wear with a bomber jacket or luxury hoodie. 

Short Shorts

This is a man wearing a pair of printed short shorts at the beach.

By short shorts, we mean shorts that end at the middle of the upper thigh. While we are using the word short, we do not mean short enough to end right below your bottom. Before you consider these shorts, you must look at your legs to determine if they are right for you.

If you have larger legs or slim legs, these may not be the best style of shorts for you. When you wear these shorts, your legs do not have anything hiding them. If you do not like the way your legs look, you should avoid these. 

Pleated Shorts

Harbor Bay by DXL Big and Tall Waist-Relaxer Pleated Twill Shorts, Khaki 48 Reg

There was a time when pleated shorts were reserved for males and females that attended private school. Now, pleated shorts are trending and among the popular shorts for men. Pleated shorts have added a slight twist to flat-front shorts.

These shorts are stylish and help any guy stand out. Pleated shorts hold on to their shape no matter how long you are sitting. These shorts give the wearer a sophisticated look, but you must be careful with what you wear with them.

You do not want to wear something that is too formal. You might want to consider a crew neck t-shirt or a nice polo shirt. 

Drawstring Shorts

This is a close look at a man wearing a pair of gray drawstring shorts at the park.

There was a time when drawstring shorts were not found out of the gym. With new designer sportswear, there has been an uptick of wearing drawstrings in other places. These are not your average sweat shorts.

They are comfortable and give an ultra casual look. These are the ultimate lounge short options. One should be careful when wearing these shorts.

They can look a lot like pajamas. It helps if you wear a pair of drawstring shorts that are a dark color. If you want shorts that are lighter, you should go for a pastel color. You want to stay away from gray.

You can pair them with a bright t-shirt or other short sleeve shirts. You want to stay away from gray and white. They are basic colors but just way too basic to pair with drawstring shorts, even for casual wear. 

Printed Shorts

This is a close look at a man wearing a pair of printed camouflage shorts.

Printed shorts have been a popular style for a long time. However, they are a type of shorts that people either love them or hate them. When they are done well, they are a perfectly striped pair.

When they are not done right, they have some crazy-looking cartoon. The best style of printed shorts for you to wear while staying fashionable is a bold stripe made of different colors or camouflage. You can pair these patterned shorts with a classic Oxford in white or a polo shirt that you leave open.

You can even consider loafers to dress up the look.

Denim Shorts

This is a close look at a man wearing a pair of jean shorts.

Denim shorts are considered an all American look. When it comes to denim shorts, you have to choose carefully. They can go wrong quickly, depending on the style.

You need to pay attention to the fit. You should stay away from denim shorts that are tight or short. When they look like that, they are dangerously close to looking like hot pants.

If they are too long and clingy, they look like something straight out of the 70s. When you wear denim shorts, you want to make sure there is room between your leg and the denim. 

Tread cautiously with what you wear when you have on denim shorts. If you want a pair that is going to hold up to some abuse, you should consider a more durable pair of shorts. The darker the denim is means the better it will hide stains.

Knee-length shorts may be a reasonable consideration for you. It is important to note that denim does not breathe as well as other fabrics, like cotton or linen shorts. Denim shorts transition well from day to evening, especially when paired with a button-down shirt.

Jean short options are much better than they used to be. 

Tailored Shorts

This is a man wearing blazers and colorful tailored shorts.

Tailored shorts are a classic look and always safe. They do tend to be slightly dull. While they are not the most original style, they certainly are versatile.

These pair nicely with just about every other classic summer style. When matched with a freshly ironed button-down, you can wear these to work. For an even cleaner look, add a lightweight blazer and a nice polished shoe.

This outfit translates nicely to upscale outdoor dining. When looking for tailored shorts, stay away from zip or flap pockets. These are not the type of shorts you want to make trendy with overly design pockets. They are a classic for a reason. They may also be called chino short.

Swim Shorts

This is a man wearing a pair of floral print swim shorts.

Swim shorts have a short season, but there is an overabundance of them on the market. The best swim shorts you can find have bold colors, fabrics that dry quickly, and a tailored look to them. While swim shorts are always in fashion in the summer, especially in beachy areas, they change drastically, or so it seems every season.

You can find a retro look that is shorter in the legs. When you opt for a bright pair of swim shorts, you want to pair it with a t-shirt that is not as bright. You can find board shorts that are long shorts or a shorter length, depending on your preference. 


How Do You Know When Shorts Fit Properly?

You want to make sure that you select shorts that fit your body type. You also want them to allow you freedom of movement. It is also critical that you are wearing the proper shorts for the event. A baggy short and cropped shorts are great causal and everyday wear.

Tailored shorts are better suited for business casual. The fabric matters, too. You should only select a dry-fit material when you are wearing these shorts to the beach or pool.

While these can be casual shorts, they are not suited for all events. 

What are the Most Comfortable Shorts for Men?

Some of this does come down to personal preference. Some men will find one type of shorts comfortable while others will hate them. You want a pair of shorts that will allow you to move freely. You may want to look for shorts that have some stretch to them.