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How to Wear Shorts

How to Wear Shorts

Wearing shorts is one of the best ways to stay cool during the summer. Shorts are perfect for weekend shenanigans, dog walks, the beach, the pool, barbecues, picnics, romantic walks in the park…you get the point.

Shorts are inherently casual, but that doesn’t mean they have to look adolescent and sloppy. So why do most men look so bad wearing shorts?Shorts bad fit


Well, they’re just not wearing them correctly. Their shorts don’t fit, and they’re not wearing the right styles.

This post teaches you how to avoid these mistakes so you look amazing wearing shorts like the laid back, stylish gent you are!

How Shorts Should Fit

To make sure your shorts flatter your body type, you need to pay attention to the length AND the width (the leg opening).

Shorts Length

Just like with swim trunks, it’s crucial that your shorts don’t go past your knees. They should stop at the top of your kneecaps (at the longest).Correct length for shorts

Ideally, your shorts will stop an inch or two above your kneecaps, but this is a matter of personal preference.

Just like pants, the length of your shorts is measured along the inseam. The best length for men under 5’9″ is 7″.

Anything longer than that will most likely be too long, although you can get away with 9″ shorts if you like them a little longer.

If you’re under 5’5″ or just want to show a little more thigh (highly recommended) you might want to wear 5″ shorts instead.

Shorts Width

After wearing shorts that are too long, the second most common mistake that guys make is wearing shorts that are too wide.Shorts too wide

Just like pants, most mass-manufactured shorts will be too wide through the leg. Unless you have thick legs, you’ll need to look for “slim fit” shorts or get your shorts tailored.

You want to avoid the trapezoid silhouette – where your shorts are wider at the bottom than the top. This happens when the leg opening (or circumference) or your shorts is a lot wider than the circumference of your leg.

It creates a bottom heavy silhouette, just like when women wear loose skirts. Great for them, bad for us.

Plus it makes your legs look thin and weak because they’re being swallowed up by your shorts.

Instead, try to achieve a nice gentle taper that follows the line of your body:

Slim fit shorts

Your shorts don’t have to be skin tight. They should be fitted and comfortable. Make sure you there’s a little wiggle room between the fabric and your skin, but not more than a couple of inches.

Fit Hacks

Just like pants, shorts can be hemmed. Or, if you don’t want to pay the tailor tax, you can also just roll your shorts up.

You can also get them tapered for $15-25 and have the waist adjusted by 1-2″ either way.

When trying on shorts, it’s most important that they fit in the seat and crotch. Everything else can be fixed.

Styles and Details

Here’s a quick list of what to avoid:

  • Cargo pockets
  • Large, bold patterns
  • Obvious branding/logos
  • Distressing (tears, rips, holes, stains)

Stick with solid colors and small scale patterns or prints. For example, if you like polka dots or floral prints, that’s totally fine. Just make sure they’re small in scale (small dots or flowers).

Doing It Right

Need some stylish inspiration? Here are some men of modest height wearing shorts the right way:

Donald Glover shorts

Scott Schuman shorts

Donalg Glover Spring Look

Where to Buy Shorts

The good news is that many brands offer sub-9″ shorts these days. Choosing the right fit for your build will take some trial and error, but here’s where to start:

  • ASOS Skinny Chino Shorts (nice and slim, plenty of taper, perfect for thin legs)
  • J. Crew 7″ Stanton (not as slim as ASOS but higher quality and great styles)
  • J. Crew Factory 7″ Reade (little cheaper than the Stantons, same overall fit)
  • Chubbies (aggressively short, pretty much the opposite of baggy cargo shorts)
  • Peter Manning (more of a classic fit, all the right details)
  • Fred Perry (expensive but nice)
  • H&M Chino Shorts (basic, slim fit, get what you pay for in terms of quality)

If you’re looking to revamp your shorts collection and find a new brand that’s perfect for you, I recommend ordering a few pairs off this list.

Once you find something that fits, order a couple of different styles and colors, then you’ll be set for a while!

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