#OOTD: The Best Way to Wear Shorts for Men This Summer

It’s time to let your legs get some sun, folks, courtesy of the best shorts for men this season. Past #OOTD entries have gone a bit more rugged, but no less casual and cool, like how to wear chukka boots this summer. Others have even shown you how to wear lightweight chinos — as in, this guide on how to wear a henley for men. But with all that being said, we’re lightening things up and going even more casual and laidback than that. Consider this the first of many posts on how to wear shorts for men this summer — and not just any shorts, but the best men’s shorts. They’re comin’ at ya, naturally, from Huckberry. Would you expect anything else? I certainly hope not. We’re wearing ’em here (or rather, I’m recommending that you wear these shorts this way in the future) with  other rugged, easygoing basics.

That makes this the kind of #OOTD fit for summer’s most lofty pursuits or its most basic, whatever that means for you. To me, it means record shopping and brewery hopping, cold beer in hand all the while (or at least, after I’ve got my records in hand). If you already know what the majority of your summer entails, and if it involves fun in the sun — which I guarantee it does — then my guide on how to wear shorts for summer should prove mighty handy. I won’t keep you here any longer, though. All the shopping tips you need for the best men’s shorts can be found below.

Best way to wear shorts for men

  • The Shorts: Flint and Tinder 365 Shorts, $64 — I’ve talked plenty about the Flint and Tinder 365 Shorts, which come in both a 7-inch and a 9-inch inseam (think longer if you’re taller). Fact of the matter is, they’re the best shorts for men if you want effective, quality style.
  • The Shirt: Wellen Hemp-Cotton Buttondown, $68 — Get yourself one of the most stylish sustainable shirts out there, with a neat pattern and breezy, eco-conscious fabric.
  • The Light Jacket: Taylor Stitch Park Bomber, $228 — Now, it might be not cold enough on a typical day for this Taylor Stitch bomber jacket. But if it gets breezy or rainy, or even chilly when the sun goes down, you’ll want this retro bomber on your back.
  • The Sneakers: Taylor Stitch x SeaVees Vista Sneakers, $88 — Consider this your recommendation to pre-fund this stylish sneakers right now, and then keep this full #OOTD around for inspiration this summer.
  • The Socks: Proof 72-Hour Merino No-Show Socks, $28 — Those Taylor Stitch x SeaVees sneakers are going to need the best no-show socks around to keep ’em versatile and stylish — these are the pair to buy.
  • The Watch: Alsta Nautoscaph Superautomatic, $1,005 — This isn’t the first time I’ve recommended this heirloom sport watch, and it won’t be the last. It’s an incredible way to add character and functional style to this #OOTD.
  • The Sunglasses: Maui Jim Cruzem Sunglasses, $250 — How about these shades? The best pair of sunglasses for men are an absolute essential. Don’t leave home without them, to say the very least.
  • The Everyday Carry: Filson Rugged Twill Original Brief, $325 — I can’t help but recommend a rugged Filson bag (one that’s also aptly named!) for your daily adventures this summer, anywhere you happen to go.

Are these tips helpful when it comes to how to wear shorts this summer? The key starts, first and foremost, with finding the best shorts for the occasion — in this case, a pair of shorts like the Flint and Tinder 365 Shorts, in an agreeable inseam and a classic color. They’re an ideal pairing with a piece that’s also an upgrade to your typical tee — one of the most stylish sustainable shirts ought to get the job done for breezy weekend style. Things don’t let up from there, though. Your Taylor Stitch bomber jacket is going to offer up lightweight comfort and necessary protection from the elements, all the while looking just great.

No #OOTD is complete without a pair of the best sneakers for men in the summer months, so your new Taylor Stitch x SeaVees sneakers are primed and ready for the occasion. Add in an heirloom sport watch, one that’s highly splurge-worthy, and you’ve just given this look a major shot in the arm. And while it might have been some time since you’ve worn Maui Jim sunglasses, why not give this ever-reliable brand a try once more? They look great to me, that much I know. Wrap it all up — and get from point A to point B — with a rugged Filson bag, the kind you’ll have for years and years to come. No matter where this #OOTD takes you, it’s going to take you there in style. See you out there, my friends.

#OOTD: A New and Improved Way to Wear Shorts This Summer

Do you ever find yourself struggling with how to wear shorts? As in, how to find the right cut, color & fabric, and then wear ’em in a way that’s unique to you … yet still friendly and fashionable (but not too fashionable) for a summer weekend? That’s what we’re here today to discuss, and we’ll start by digging into the stylish shorts from Flint and Tinder that are going to set you apart from the pack. Looking for slim, tailored shorts that hit above the knee is the first critical step, and then finding the right summer men’s style essentials — like a classic navy polo and a pair of the best men’s sneakers on the market right now. It’s not just about grabbing a great pair of shorts, then throwing on whatever is in reach. In fact, each of these picks are just a little more stylish and visually interesting than the gear you might be used to wearing with shorts, and that means you can take this #OOTD a heck of a lot of places. Which is to say: For a relaxing summer day at home or on the road, the Flint and Tinder Weekend Shorts are only the start of a stylish, fun day. BBQs, breweries, summer celebrations aplenty … this is how to wear shorts for all of those occasions.

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The very best way to wear shorts? Well, it’s certainly one way!

  • The Shorts: Flint and Tinder Weekend Shorts, $78 — These stylish shorts from Flint and Tinder live up to their name, easily. They’re laidback and ready for … the weekend.
  • The Polo: Relwen Stripe Slot Pique Polo, $98 — How can you not love Relwen’s take on the classic navy polo? This is a visually interesting change of pace as far as the best men’s polos go, and it pairs perfectly with new & improved shorts.
  • The Classic Sneakers: SeaVees Legend Chambray Sneakers, $88 — When the weather gets nice and breezy, you should turn toward some of the best men’s sneakers on the market, this time in a summer-friendly chambray.
  • The No-Show Socks: Proof 72-Hour Merino No-Show Socks, $29 — Let’s account for all the small details with these stylish no-show socks from Proof, shall we?
  • The Sunglasses: Raen Optics Wiley Sunglasses, $135 — These are no run-of-the-mill sunglasses here, no sir. These are some of the best sunglasses you can reach for this season, blending modern style and old-school cool.
  • The Everyday Bag: WP Standard Canvas Travel Bag, $289 — Be it a trip to the store or a trip to the park, this dependable everyday bag from WP Standard can hold all the gear you need — and then some.
  • The Wallet: Filson Bi-Fold Wallet, $135 — Whether you hit up your favorite BBQ joint or grab a scoop (or four) of ice cream, this Filson wallet is going to carry your cards and cash in style.
  • The Grooming Essential: Duke Cannon 2-in-1 Shampoo & Conditioner, $14 — Hey, summer is no time to let your grooming slip — use Duke Cannon essentials, like this great-smelling shampoo & conditioner, to take care of business.

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Before you head to your next BBQ or casual weekend brunch, are you feeling more acquainted with how to wear shorts? Namely, new & improved shorts from a favorite brand like Flint and Tinder? Starting with a foundational item as great as those shorts, what with their weekend-ready vibe (literally!) only sets you off on precisely the right foot. The right supporting cast also makes all the difference, which is why we’re recommending you wear a classic navy polo with just a bit of a twist — the same can be said for those SeaVees sneakers, assuredly some of the best men’s sneakers you can pick up at the moment. Of course, it’s critical that you pair up those sneakers with stylish no-show socks to keep your feet & your sneakers in great shape. And no matter where you go (the beach? a road trip?), a dependable everyday bag from WP Standard is one way to carry your everyday essentials while standing out from the pack. The little details, as ever, also matter — you won’t be leaving behind your Filson wallet anywhere, I can guarantee that. And if you choose to outfit yourself with some of the best sunglasses your money can buy, then your #OOTD gets all the more stylish and summer-ready. But really, things get off on an even better foot when you use a great-smelling shampoo & conditioner, then dress accordingly with stylish shorts. How do you plan to wear this #OOTD? Let me know on Twitter. Thanks for reading!