What comes to mind when you think of stylish men’s shorts? Well-fitting. Slightly above the knee length. Classic fabric and design.
The best men’s shorts are as perfect-fitting as your favorite pair of chinos or trousers. It’s 2020, after all, and there’s no reason you can’t find great, well-fitting shorts to wear.
In this article, I’m gonna link you to my favorite shorts for the upcoming warm weather season.
Read ’til the very end; I have a few pointers and cues to make sure your entire fit looks awesome.
Also got a few tips if you have a tough time pulling off shorts and don’t consider yourself a “shorts guy”.
My Recommendations For the Best Men’s Shorts
1. Bonobos Stretch Washed chino shorts
The Stretch Washed Chinos from Bonobos are among my favorite and most recommended chinos for at least the past 5 years. So I can confidently say their stretch washed chino shorts won’t be any different.
These chino shorts have 5″, 7″, 9″, and 11″ inseam options. And with a 98/2 cotton/lycra blend, you get more cotton twill handfeel, but with enough stretch for comfort.
Bonobos, in general, make a great pair of pants. They started with pants, they perfected the formula, and no matter what body type you have, you’ll find a pair here that fits you well.
flint and tinder 365 Shorts
Looking for an all-around casual-but-sharp style situation that works on the weekends… correct? If so, here’s your new favorite pair of men’s shorts.
Feel free to kick back on your patio with the American-made Flint and Tinder 365 Shorts. Tons of colors (#menswearneutrals) in both 7″ and 9″ options.
Throw on a loose, breezy short sleeve button-up
3. Everlane Performance Chino Shorts
The Everlane Performance chino shorts look like your classic flat-front 100% cotton style, but with comfortable 4-way stretch built in.
(The fabric has a 94% cotton, 6% elastane blend)
4. Banana Republic linen cotton shorts
Another fabric option that will keep you cool in hot weather is a linen / cotton blend.
These slim linen cotton shorts from Banana Republic are a great example.
Classically styled in summer-appropriate colors, you can wear these with a bunch of different outfits.
“Can I really pull off shorts?”
Of course you can!
Even if you don’t consider yourself a “shorts guy,” we’re here to change your mind.
The rules of wearing shorts are a bit different nowadays. Shorts are no longer the last resort, throw-it-on-and-hit-the-road move they might have been in the past.
No sir, the best men’s shorts have enough personality and style to work for any guy, and can keep you cool throughout the spring and summer seasons.
You don’t have to swap in shorts for every outfit just because it’s hot out, but with these sharp-looking options, you now have the choice, at least.
As far as what to wear with shorts?
You’re gonna be dressed more casually overall.
So think more (well fitting) tees, polos, short sleeve button-ups, casual linen shirts.
For shoes, probably minimal sneakers, loafers, or flip flops (if you’re near a body of water only).
You have plenty of options!
Check the Spectrum of Style Formality if you’re not sure where your clothing lies on the casual/formal range.
Check This One Out, Too!
Your shorts just got a serious upgrade, gentlemen.
How men’s shorts should fit
So, what kind of shorts do you want to avoid?
You’ve seen it. Baggy, sloppy cargo shorts that we’ve all worn (some—myself included!—for far too long).
A few key points to remember about how shorts should fit:
Most shorts come in different inseam lengths, usually: 5″, 7″, 9″, and 11″. Choose the right inseam based on your height / leg length.
The hem should hit anywhere from mid-thigh to right above the knee. Most guys go for the 7″ and 9″ lengths.
Don’t go too long—anything past the top of your knee starts to look weird and not as sharp. Also throws off your proportions.
Fit / leg width
Your shorts should fit like your best pair of chinos. They just so happen to not have the full leg that pants do 😉
Think of it this way: if you can fit a couple fists up the leg of your shorts, they’re too wide. You would never wear pants that wide, y’know?
Keep em slim and tailored, regardless if you have chicken legs or tree trunks.
The key is proportion. If you have skinny legs and wear huge, wide shorts, it makes your legs look even smaller. And if you have bigger legs, wearing long, wide shorts just makes you look huge.
The most Lean Wardrobe-friendly pairs of shorts are minimal, with simple slant pockets (similar to your chinos), welt pockets on the back, a standard waistband, and belt loops.
Obviously no cargo pockets, no extra decorative stitching. Just simple, clean, and classic!
There will be variations on this classic style in our recommendations. Use your best judgement.
A drawstring short, for example, is more casual… whereas a sharp pair of classically styled shorts as described above can be worn in slightly dressier situations—e.g. al fresco dinner and drinks, outdoor bbqs, etc.
Always do a bit of research before slapping on some shorts this summer. You want to make sure what you wear is appropriate for the venue, the crowd, and the event you’re attending.
Ready to look sharp in shorts this summer?
What’s your favorite pair of shorts from this year’s updated list? And how do you plan on wearing them?