Wearing shorts is one of the best ways to stay cool and casual when it’s hot outside. Here’s how to wear shorts properly (and how your shorts should fit).
Shorts are perfect for weekend shenanigans, dog walks, the beach, the pool, barbecues, picnics, romantic walks in the park…you get the point.
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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?
Well, they’re just not wearing them correctly. Their shorts don’t fit properly, and they’re not wearing the right styles.
This guide teaches you how to avoid these mistakes so you look amazing wearing shorts, just like the laid back, stylish gent you really 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).
Let’s start with the 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).
I like my shorts a little shorter, so most of my short stop 2-3 inches above my knees. This is a matter of personal preference, but I don’t think any man looks good with shorts that go past his knees.
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.
After wearing shorts that are too long, the second most common mistake that guys make is wearing shorts that are 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:
Your shorts don’t have to be skin tight. They should be fitted and comfortable, and you should be able to move around.
Make sure you there’s a little wiggle room between the fabric and your skin, but not more than a couple of inches.
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 (including the waist).
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).
That said, solid colors like tan, khaki, black, navy, grey and olive are always a safe and classy choice.
Doing It Right
Need some stylish inspiration? Here are some men of modest height wearing shorts the right way:
Where to Buy Shorts
UPDATE (April 2017): Tried on a few popular “mall brands” to see how they fit:
The good news is that many brands offer stylish shorts in a variety of fits. Choosing the right fit for your build will take some trial and error, but here’s where to start:
- Topman Skinny Chino (my current favorites)
- Outlier New Way Shorts (not quite as tapered, but very high quality)
- ASOS Skinny Chino Shorts (super slim, perfect for cuffing, but very low quality)
- 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, better for guys with big thighs, decidedly preppy)
- H&M Chino Shorts (basic, slim fit, not great 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!
What’s your favorite pair of shorts? Leave a comment below!