Should Men Wear Shorts in 2021? | How to Wear Shorts

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Show of hands (I can’t see you but I’m assuming you’re participating and I’m sure your FBI camera guy can verify): who wears shorts because you actually like to?

Yes, I know we're in the middle of winter, and shorts are probably the last thing on your mind in this instant, BUT you know spring will be here soon so we need to talk shorts for 2021.

From some informal surveying (aka hosting a poll on my IG posts and stories) it sounds like a lot of us would rather wear pants even in the summer heat.

That’s right! Whether it’s their design/lack of it or self-consciousness of showing some leg, most of the men I’ve talked to would rather wear pants year-round than find the right pair of shorts. For a lot of us it just gets so hot in the summer we have no choice.

Men need shorts, but do we want them?

I’m guilty of it. Up until this year, I wore shorts out of necessity. I tended to give up on my spring and summer style in general.

BUT we're changing that for the new year. Since my goal is to help you feel good in your clothes year-round, I want to give you a guide to wearing shorts in 2021.

No more throwaway shorts styles!

We’re talking when to wear shorts, how your shorts should fit and how to wear them, and what to look for in your next pair of shorts for 2021. By the end of this, you’ll have, dare I say, the best men’s shorts guide AND we’re going to get you excited to wear shorts again!

When to Wear Shorts for Men

For the record, we’re not talking swim trunks, athletic shorts, bicycle shorts, or anything other than shorts you can wear everyday. Let’s say the types of shorts for men here are style-forward shorts ready for daily-wear. That’s our focus.

A Short, Shorts History - Why don’t men want to wear shorts?

Before we get into when we should wear shorts in 2021, indulge me for a second on why men don’t want to wear them. A brief history:

Flashback to the late 19th and 20th centuries, shorts (Knickerbockers or Knee Pants) were mainly worn by young boys. They also became popular in the 20th century for sports.

Adult men wouldn’t typically step out in a pair of knee pants in normal settings. It was too casual and immature. There was also an introduction of shorts (Bermuda style) around that time to military personnel. Those serving would cut their pants at the knee before to get relief from the heat.

Men did not wear shorts on a regular basis.

See? Very brief shorts history. You can check out some accompanying articles and blogs that I got this info from at the end of this post.

Shorts were for boys, not men and were considered very informal.

Men’s Shorts in 2021

Is it wrong to wear shorts? No. Should men wear shorts today? Yes! Shorts have become wildly more popular in the US and a necessity in most summer climates.

Here’s the catch: shorts are still casual! Regardless of the shorts style you rock, keep them to your backyard bbq’s, daily errands, and day-to-day style. Even if you rock a suited shorts combo, the lack of pant leg and exposed calves makes them inherently more casual.

Short and simple: If you’re conducting business or attending formal events, no shorts. If you’re casually spending the day with friends, shorts it up!

How to Wear Shorts (with style)

There are a few elements to explore when it comes to dissecting how to wear shorts, so I’m going to break it down into fit, type, and colors and patterns. That should cover all our men’s casual shorts wearing bases.

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How Your Shorts Should Fit

What are you really asking when you ask how your shorts should fit? I’m guessing it’s how much quad is too much quad, right? The right length of shorts for men is always a hot topic. The guidelines for shorts length are actually pretty simple:

  1. Shorts should not go below the knee. That’s an outdated look and will make you look shorter.
  2. Figure out how much leg you’re comfortable showing. Shorts typically come in 5”-9” inseams but vary by brand. The shorter you are in physical height, the shorter you can go in your inseam to keep things proportional. Try different lengths to see what’s comfortable.
  3. When in doubt, keep your shorts about 2” above your knee. That will lend you the most modern design. If you haven’t been skipping leg day, show off a little more!

The shape of your shorts matters too.

When figuring out your ideal shorts length, make sure you’re also thinking about shape. Stay away from wide and baggy leg openings. It creates an unflattering shape, especially the shorter you go. I have a feeling you’re not going to want to look like you’re wearing parachute shorts.

Shorts leg opening shouldn’t be too wide or too tight.

At the same time, avoid too tight of a leg opening. We're looking for enough room to be comfortable while sitting and standing. Just like Goldie Locks, you’re going to want to find the pair that is just right (and preferably that did not belong to any bears).

Stick with slim or straight silhouettes in your shorts for clean lines. Make sure to experiment with this to find your ideal shorts profile.

The Types of Shorts You Need (or Don’t)

It’s easier to list the shorts you want to avoid: Cargo Shorts (duh), Athletic Shorts, and any other shorts reserved for specific activities and not daily wear.

Cargo Shorts - By now if you don’t know that cargo shorts are out, you probably haven’t read enough menswear blogs. They are one of the main culprits of creating the trapezoidal shape that we we recently agreed isn’t modern or accentuating anything you want it to (you remember that conversation, right?).

Too many pockets add bulk. These are a dead giveaway of throwaway style. If you’re considering a pair, ask yourself if you’re going on a multiple day hike or working for Tiger King. If your answers are no, skip them!

Athletic Shorts - Don’t get mad at me. I’m only saying that we don’t want to allow athletic shorts to become your everyday apparel. Once you start wearing them outside of the gym (or errands right after) your wardrobe falls into a looser and sloppier place. That’s not what your personal style should say!

If you are going to be in athletic shorts quite a bit, invest in some nicer quality ones that aren’t ripped or stained and still have a good structure to them to address the fit of the shorts.

Get shorts that look like real clothes.

Let’s focus on cotton, chino, and linen shorts. Find materials that are comfortable, have some structure to them (aka look like real clothes) and meet our fit criteria.

Colors and Patterns for Shorts

Fit. Check. Type. Check. Now what about colors and patterns?

Well, lets break it down into three categories:

Neutral Colors - These are going to be your most versatile shorts that will go with any summer tops. Think about beige or khaki, navy, and even olive colored shorts. If you’re a shorts beginner, start with 1 or 2 pairs of these.

Bold Colors - Once you’re set on neutrals, hop into some bold colors. Now we’re talking red, yellow, pink, and anything that is more vibrant and saturated than your neutral colors.

Style Hint: Buy bold color shorts from the same brands as your neutral colors. The fit will be the same.

Patterns - Your final destination will be patterned shorts. Patterned shorts can be more difficult to style than pants. You get much less real estate for the pattern, so I tend to stick to simpler ones. Expert level shorts-ing right here.

So, are you wearing shorts wrong? If you’re thinking it might be a yes, it’s time to focus on length, shape and the right type of shorts for you. Cover these bases and you’ll be a pro at wearing shorts with style.

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I am a freelance men's fashion and lifestyle digital content creator, social media coach and consultant, and brand strategist. Follow along for articles related to style how-to's, fashion trends, and content creation business behind the scenes and strategy tips.

Denver, CO
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