How To Wear Shorts: A Guide For Shorter Men

Finding Affordable Shorts With The Perfect Fit

Style

By ShortNStylish

Published August 2024

Looking your best at all times is the goal. One area our shorter brethren tends to get wrong is how to wear a pair of shorts. With summer winding down and season clearance sales in full swing, this is one area we want to tackle so you can take advantage.

You should know how to wear shorts and pick options that suit not just your height and overall physique, but help you to properly achieve the aesthetic you’re aiming for. Subtle differences in shorts length for example can ruin what would otherwise be a great look. Once again, have no worries, we here at Short Kingz will put you on the right track!


See Also: Stepping Up Your Short Man Sock Game


In this article, we are going to discuss the key tips and strategies to help you select the perfect pair of shorts. We will also cover the different types of shorts as well as the style options so you feel comfortable in your summer wardrobe.
 

THE SHORTS FITTING GUIDE FOR SHORTER MEN

How to wear shorts perfectly as a shorter guy requires a solid understanding of the clothing fit. Therefore, you should consider a few factors when shopping for shorts in order to find a pair that best suits your body type.
 

  • Length: Firstly, you should consider the length of the shorts, which can be measured from the top (waistband) to the bottom (hem). For the inseam measurement (inner length from the center), you should consider the point where the crotch and leg seams meet down to the bottom of the shorts. Remember, your shorts should be short (which is hte whole point) and in most cases, should stop a little bit above to around three inches above your kneecaps.
  • Width: The width is another factor that you should pay attention to for a good fit. Make sure your shorts are snug to your legs the same way your pants would. Take a pinch test and check if you can pinch 1 to 2 inches of the short fabric at your thigh. If yes, then those shorts are good to go! You do need some breathing room, but no reason to overdo it. For the time being at least, baggy is out.
  • Waist: Measure your waist using sewing measuring tape, ensuring the tape around your waist is snug but not too tight. Then, button up the shorts, lay them flat on a table, and take measurements from one side to the other. For accurate numbers, double this measurement, and you'll have the ideal fit.
  • Rise: As far as the short’s rise is concerned, you should take the length from the fork (the point where the legs meet the crotch) to the top edge, also known as the fly.
  • Hip: The hip area on shorts are usually 1.5 to 2 inches below the zipper. Once again,  use that sewing measurement tape and carefully note the size of your hip for the best fit. 


All of this is great for your own knowledge and will help with doing orders online. Nothing is better however in my opinion that getting professionally measured and trying items on in your local brick and mortar for accuracy and reassurance.
 

TYPES OF SHORTS FOR SHORTER MEN

Here are some types of shorts for short men. Now realistically, this applies to all men, but this is a site for shorter men, so we will frame it as such. We will also discuss how to wear shorts of every type:


DRESS SHORTS FOR SHORTER GUYS

If you want something less casual and more formal look for a date, event or night out, here are some dress shorts options you can try:

PLEATED FLAT FRONT

Pleated shorts for men, as the name suggests, have a crease that resembles the crease on Chino pants. Previously known colloquially as “Dad Shorts” or “Preppy Shorts”, they are making a comeback and gaining wide popularity with the younger crowd.

The pleats give these shorts a dressier, freshly ironed look. On special occasions like a romantic date, office or boat parties, you can wear them with a solid Cashmere or Henley T-shirt or a light-colored button-down.

BERMUDA

Bermuda shorts, also known as “walk shorts”, are small trouser-like shorts. Think of them as being the same as above without the pleat. They are typically knee length, and the hem can both cuffed off the rack or hand cuffed by you. You can wear them to your business meetings by pairing them with a dress shirt tucked in or pair them linen or plaid shirts with the sleeves rolled up. Some opt to wear a blazer, dress shirt, tie and socks with these. While you can do anything you want, we’d suggest staying away from that and going with a full suit instead.

Dockers have always been my go-to for Bermuda styled shorts. They’re affordable, comfortable, breathable and come in a variety of masculine colors and prints.


CASUAL SHORTS STYLES FOR SHORTER MEN

For the everyday short guy, those aspiring for comfort and a day of hanging out have the following options:

CARGO

If you need to look chic and cool, you cannot go wrong with cargo shorts. These shorts often feature two pockets at the waist, two at the bottom of each side, and two at the back, which are useful for carrying all your essentials.

Some have velcro pockets and visible seams while others opt for zippered pockets and a flatter look.. Overall, the material of cargo shorts is comfortable as they are typically made of stretchy fabric and 100% cotton. You can pair them with a half-sleeved button-up or shirts with design patterns. For footwear, monochrome sneakers can help achieve a softer, more minimalist, yet urban look.

Carhart, Wrangler and Old Navy shorts always fit the bill. Affordable, available in hard colors, breathable fabric and easy to care.

DENIM

Denim never goes out of style, and the same is true of denim shorts. These shorts come in a variety of colors, from indigo to faded blue, and you can pick the one that best suits your aesthetic preferences.

You should also be careful about the fitting of the denim shorts and ensure you opt for shorts that aren't too tight. There should be enough room between your legs and the denim fabric so you don't end up feeling like you are restricted and have a flattering look.

Also, consider whether your denim will be distressed and have faux-rips, or if they will have a unform grain and flatter appearance. It will make the difference between casual or more urban, youthful aesthetic.

Everyone is picky with their denim. For me, I am a huge fan of rips with patches underneath them so the skin isn’t exposed. I also like lighter and dense blues. Express For Men sometimes has the style I am looking for. On Amazon, these shorts by Hengao and Betsuline are right up my alley.

MADRAS

Another casual shorts option is Madras shorts. These shorts were named after the Indian city of Madras and entered the fashion world in the 1940s.

These shorts range from vibrant patterns all over to having a more dressy plaid pattern. Either way wearing them will turn heads. The fabric is lightweight cotton, and you can pair them with any muted solid T-shirt to make a fashion statement. These go in and out of style, but worn right, will point to your keen sense of fashion.

To be on the safe side, we’d recommend wearing low top monochrome sneakers and a solid polo or tee for a look that borders casual and preppy. Pairing these with boat shoes will give you a golfer look.

While Brooks Brothers isn’t cheap, they usually mark their items down near the end of the season. These cotton patchwork shorts from Brooks Brothers are vivid in color, but can pair nicely with loafers, boat shoes or low-top sneakers. For more predictable professional patterns, Allelms has a great selection.
 

SPORTS AND ATHLETIC SHORTER FOR SHORTER MEN

If you’re shorter guy who is also athletic, you can try these short types

RUNNING SHORTS

Usually made from polyester, running shorts allow for easy movement. They are breathable, and the inner lining allows for extra comfort. These shorts aren't too long and may reach mid-thigh to avoid any discomfort.

CYCLING SHORTS

Cycling shorts are actually skin-tight garments that ensure that the safety pad stays in place and there's no extra material that may get stuck in the cycle. The best part is that these shorts soak up sweat and water, reducing friction.

BOARD SHORTS

These shorts are quite lengthy and graze your knee. Firstly, they were introduced as swimwear; however, now, they’re even worn casually. You will find these shorts in a variety of colors and patterns, so you may pick the one that suits your taste. Pair these up with a tee shirt and either sandals are flip-flops for a day at the beach or to hang out around the way.
 

TOP STYLES TO WEAR SHORTS FOR SHORTER MEN

Some of the top styles of how to wear shorts are given as:

URBAN STYLE

Urban, or street style clothing, typically associated with inner city life and influence in the U.S is popular worldwide. Urban styles include Cargo, Denim and Madras. With the exception of Madras which typically come in vibrant patterns, you can wear these shorts types with shirts which feature bold patterns, colors, and detailing or go solid. Pairing these shorts with denim jackets or t-shirts with brand logos or graphics will give an edgy, youthful and trendy look. Sold colored shirts will complement the older crowd better giving off a bit of edge, but adding layers of maturity and class that are both associated with experience.

PREPPY STYLE

The preppy style originated from  Ivy League fashion in the 20th century and involves clean and timeless clothing pieces. So, if you are wondering how to wear shorts in a preppy style, you should opt for shorts in pastel colors and subtle patterns. Combine them with dress shirts with rolled sleeves or polo shirts for a more sophisticated and elegant look. Always go for low top sneakers or boat shoes to add the extra “prep” in your step.
 

THE DON'TS OF WEARING SHORTS FOR SHORTER MEN

Now that you are aware of how to wear shorts, let's discuss a few don'ts that you should never overlook. Don’t do the following:

Short Kings | Short Men's Shorts Style Guide

  • Wear shorts that are too long; the ideal length is just a little above the kneecaps. There is always a debate on this. When I was a younger guy and shorts that went below the knees were popular with the youth, a teacher once quipped “are those long shorts, or short pants?!”. If you’re doing for “longer shorts”, covering the knee caps will work, but anything below that is far from ideal, even when considering urban styles.
  • Opt for baggy shorts: These are currently out of style and look unflattering. The 1990s-2000s were the heyday for baggy pants and shorts. Unless they make a comeback (anything is possible), you will look dated and out of place. If you’re an older short man, you’ll look you’re still hanging onto your youth.
  • Wear too long or droopy shirts with shorts: These can create a sloppy and unbalanced appearance. This look will give the illusion of a very long torso which will look unnatural.
  • Wear shorts that show your back or backside: Please stop it! These don't give short men a clean look. We know that we may get push-back on this, but pull your pants and shorts up!
     

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CONCLUSION

The answer to how to wear shorts perfectly as a short man depends on many factors, including a snug fit and the type of shorts you choose. As mentioned, consider your body type, measurements and look you are attempting to achieve. That said, if you are looking for some more styling tips for short men, Short Kingz is the best platform. Join our community and check out more articles on our blog to explore more fashion advice and elevate your style game!
 

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