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.
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!
Table of Contents
How Men’s 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…
Shorts Length: How Long Should Men’s Shorts Be?
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.
Shorts Width (Leg Opening)
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, many 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.
Slim Fit vs. Classic Fit Shorts
One easy way to ensure your shorts aren’t too wide is by looking for “slim fit” on the label. This difference in cut seems subtle, but it makes all the difference.
Unless you have big thighs and hamstrings, slim fit shorts will probably be your best option. Remember, most U.S. brands are making shorts for the average American guy (who’s about 5’9″ and slightly overweight).
On top of that, most American men like looser fitting clothes, so “classic fit” (or straight leg) shorts are going to have plenty of room through the leg and a wider leg opening.
Slim fit shorts will have a slimmer thigh and a bit more taper down to the leg opening.
Remember: not all slim fit shorts are created equal. There’s no universal definition of slim fit, so different brands offer different silhouettes.
The best way to figure out which brands work for you is to try them on. Most brands, like Amazon and Bonobos, offer free shipping and returns, so it’s easy to try on a few pairs at home, then only keep the ones you like.
Make Your Shorts Fit Better
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.
When trying on shorts, it’s most important that they fit in the seat and crotch. Everything else can be fixed (including the waist).
You can also get them tapered for $15-25 and have the waist adjusted by 1-2″ either way.
Men’s Shorts Styles & Aesthetic
You can wear whatever you like, but if you’re going for a somewhat mature and timeless look, here’s a quick list of what to avoid:
- Cargo pockets
- Large, bold patterns
- Bright, saturated colors
- 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).
Solid colors like tan, khaki, black, navy, grey and olive are always a safe and classy choice. If you’re not sure which colors work best, check out our guide to neutral menswear colors.
When in doubt, a pair of khaki chino shorts is a solid option that will go with almost any shirt.
Men’s Shorts Outfit Ideas
Need some stylish inspiration? Here are some examples of guys looking great in shorts:
Now you know how shorts should fit and how to wear shorts, you might be thinking, “Hmm, I could use a new pair of shorts…or three.”
I’ve got you covered!
Where to Buy Men’s Shorts
There are so many great places to buy men’s shorts – especially chino shorts and tech shorts – it’s hard to list them all. Here are a few of TMM’s current favorite brands:
- Topman Skinny Chino Shorts – actual skinny fit shorts; only good for very slender legs
- ASOS Skinny Chino Shorts – similar fit to Topman but much more affordable (and lower quality)
- Amazon Essentials Slim Fit 7″ Shorts – super affordable; subtly slim fit
- Amazon Goodthreads Slim Fit 7″ Drawstring Shorts – more comfortable and casual than most chino shorts
- Outlier New Way Shorts (slim-straight; bulletproof)
- Bonobos Stretch Washed Shorts – available in 3 different lengths and fits (I prefer 7″ slim fit)
- J.Crew 7″ Stretch Short – tons of color options to choose from; subtly slim fit (not even close to skinny)
- Goodfellow 7″ Slim Fit Chino Shorts – good quality for the price; not super slim
- Bearbottom Stretch Shorts – many different lengths and styles to choose from; read our full Bearbottom review
- Ash & Erie Shorts – limited color selection but great fit on my 5″6″ slender frame
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!