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 perfectly fitting as your favorite pair of chinos or trousers. 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. I’ve split them up into four categories:
- Tailored / Everyday shorts (casual and smart casual)
- Basketball shorts (casual and active)
- Swim shorts (active, occasion-specific)
- Active shorts (casual and active)
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”.
Smart Casual tailored & Everyday Shorts
Madewell Pleated Line Shorts
The perfect combination of sporty and dressy.
These tailored shorts from Madewell feature a 5.5” inseam, and while shorter shorts are trending, these wear longer than the measurements would suggest. I picture these shorts on Robert Redford in Out of Africa.
Throw these on with a white or tan
Todd Snyder 7″ Pleated Hudson Short
These Todd Snyder shorts are cut from the same cloth as the Madewell pair above, except with more luxurious, elevated features.
They are longer, sporting a 7” inseam, with a slimmer silhouette, making them good for any occasion. Still, these tailored shorts remind me of adventure.
They’re great for your summer safari aesthetic, the tennis club, or just running errands on the countryside.
Banana Republic 5” Core Short
I dig these core shorts by Banana Republic because they come with advanced temperature heating technology.
Simply put: they’re warmer when the temperature cools and vice versa. Enjoy them in a wide array of colors, though Olive Green and Red Embers are my favorites.
They are wrinkle-resistant, so feel free to play football in them in the park before a dinner reservation. You won’t worry about showing up with sloppy-looking, wrinkled shorts on.
Todd Snyder Weekend Corduroy Shorts
I love corduroy – it’s one of the most underrated fabrics that we have at our disposal.
I have a navy suede chore coat from Banana Republic that feels elegant and classy on me (and I didn’t break the bank on it).
These maroon Todd Snyder shorts are a fun way to incorporate some tasteful color into your summer outfits Throw on a camp collar or a t-shirt with sandals to complete to look.
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
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)
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.
Basketball Shorts For Loungin’ (or Ballin’)
Aime Leon Dore Crest Gym Shorts
Basketball shorts are stylish again! Remember in the early 2000s when everyone was wearing those massive, baggy basketball shorts? I do, and I still cringe at the photos of me wearing shorts that went down to my ankles.
These days, basketball shorts are much more refined with several brands offering an elevated take on simple basketball shorts. I purchased hoop shorts from Aimé Leon Dore in last season’s brown colorway.
They’re more durable than most shorts you’d find at this price point. These are obviously sporty, but I’ve worn them with a long sleeve sport
Champion Mesh Shorts
At $23, these are hard to pass up. Champion basketball shorts are the blueprint for all the other shorts that came afterward.
They may be a little long at 9”, but you can hike them up if they’re too long for you. I own several pairs in different colors. I love them.
They’re unrivaled in comfort and great for anything from running errands to going for a run. Bonus points for the deep pockets if you need to hold your wallet or phone and don’t want to bring a bag.
Nike Dri-FIT Basketball Shorts
Sometimes shorts should be fun, colorful, and functional. No one is making athletic clothing like Nike, and these shorts are no exception.
They come in several festive colorways, but the gold color is calling my name. These would look best with white sneakers and a t-shirt.
Swim Shorts For The Pool & Beach
Saturdays NYC Talley Swim Shorts
A simple black swim short during the warm months is as timeless as they come.
Saturdays NYC is a great elevated menswear brand founded in 2009 that fancied itself as a “cool kid brand that bridges uptown and downtown fashion.”
14 years later and they’re still one of the premier NYC brands at the mid-level price point.
There may be cheaper black swimsuits on the market, but there is no better way to buy into a prestige brand like Saturdays NYC than with a built-to-last swimsuit that will be with you for years.
Abercrombie Pull-on Swim Short
Let’s create a little atmosphere here. You’re on vacation, the South of France perhaps.
You’re sitting beachside with a mint julep in hand. The sun is warm, the perfect temperature to keep you comfortable without beads of sweat running down your body.
You’re reading a copy of an old Fitzgerald book, Tender is the Night, and you’re reminiscing about what life must have been like on the French Riviera in the 1920s.
What are you wearing? Of course, you’re stunting in these beautiful Abercrombie shorts. This pair looks like a watercolor painting. Wear them on your European getaway, or, you know, to a local pool. Anything goes.
Banana Republic Retromarine 6” Short
You’d want swim shorts that you can take from the beach to the city without much fuss. Enter the Banana Republic Retromarine short.
In my opinion, 6” is the perfect sweet spot for a swimsuit. The strong, solid-colored shorts are bright and festive for the pool while also passing for chino shorts if you decide to wear them in the city.
No one at the grocery store will know that you’re wearing a swimsuit.
Ripa Ripa Paraggi Striped Swim Shorts
If you want to quickly channel your inner Dicky Greenleaf from The Talented Mr. Ripley, this is your shortcut.
Ripa Ripa is making a big splash in the swimwear game recently and these handcrafted striped shorts are a certified hit. They feature a quick-dry technology, so they’re made to be worn all day, whether or not you’re near the water.
These would look terrific with a knitted polo
Active Shorts For Your Next Excursion
Uniqlo Geared Shorts
It’s not a Chris Xavier article if I don’t mention Uniqlo at least once. I don’t usually like cargo shorts, but these aren’t the same ones from the early 2000s that you wore in college.
These are minimal and chic. The refined-looking shorts come in six colors, purple being my favorite.
They’re belted, which makes them the perfect go-anywhere, do-anything shorts for the summer. At $40, they’re ready to climb mountains!
The North Face Classic V Belted Shorts
Wow, these are cool. Again, cargo shorts seem to be evolving.
I really love these green shorts by The North Face; I’m considering buying a pair for myself. They have 4 pockets, so you’ll be able to carry most of your essentials on your person.
I’m also a fan of the contrasting details of the included belt and zipper loops. They’d normally set you back $65, but they’re currently on sale for $52 for a limited time only, so act fast!
Columbia Brewha Shorts
“Brewha” is fun to say. C’mon, say it with me. “Brew-HA.” Anyway, this is the third active cargo short to complete the trifecta of chic, new-age cargo shorts that I’m always recommending.
These classic fit, elastic waist shorts feature sun protection – showing Columbia is taking the task of creating the best active shorts very seriously.
Fashion boys’ favorite shorts. The Patagonia Baggie is a staple of stylish, modern dressing.
Other brands have caught up and made very good alternatives to the Baggie, but Patagonia’s cash cow shorts still reign supreme. They come in every color under the sun and have two lengths – classic 5” and 6.5”.
Check out this “Tiffany” colorway to be a differentiator in the sea of black Baggies you’ll see on the street.
Fear of God Essentials Short
If you want a look that leans heavier towards streetwear, then look no further than these Fear of God Essentials shorts.
They’re 80/20 cotton and polyester with an elastic waist and an elongated drawstring, which makes them perfect for comfort. If the hype is what you crave, then these are the shorts for you.
They’re under $100, which is hard to beat with the Fear of God name attached to it.
“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
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.
For the cleanest and most classic looks, obviously avoid cargo pockets or extra decorative stitching.
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 in the first section 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?
|07/06/2023||Added 16 new options, added categories|
|04/01/2022||Updates to text, updated links|
|05/20/2020||Original publish date|