We can’t blame you for being a little apprehensive about sporting shorts and swim trunks. After all, many of our formative years were spent wearing poorly fitting clothes in an array of colors that no one under the age of 65 should ever touch. But we’re not talking about the bulky, schlubby, way-too-long, capri pant-inspired, plaid eyesores of yesteryear. Today’s shorts are trim, flattering, and easy to incorporate into your most polished weekend and vacation looks.

As with everything, it’s all about fit. A modern man should rock his shorts and trunks just above the knee. Not only will this make your legs look longer, it will also allow for more experimentation in terms of prints and fabrics, since the trimmer silhouette offers less “look.” If it worked for style icons like JFK and Steve McQueen, it can work for you. Join us as we explore the brave new world of stylish, fitted shorts.

Chino shorts needn’t be snoozy. Instead of the normal khaki- and cream-colored varieties, experiment with some funkier tones, like these affordable, yellow-tinged joints from Uniqlo. When styled with a white Oxford shirt and some Vans, a slightly offbeat short is one part punk, one part preppy, and totally interesting in all the right ways.

Embrace your inner hype beast with a pair of bold, all-over print shorts. The key to rocking statement pieces is to let them shine by styling them with super low-key basics. You could sport these dope Champion shorts with a plain white tee and some Nike Air Force 1s—and just like that, you’re king of the block.

For a more refined look, you can never go wrong with some linen shorts in a classic color like navy. Not only will they add some interesting texture to any ensemble, they can be easily dressed up or down to match your mood. Pro tip: These look awesome with anything except a blazer. Instead, pair them with a slick polo and some Gucci loafers for a neo-prep vibe.

Did you ever think you would see the day when sweat shorts would be part of a hip, balanced wardrobe? The key to pulling off this look is to go luxe and get a pair with some handsome details, like these perfectly tailored heather grey athletic-inspired shorts cut from moisture-wicking lightweight wool.

These days, a ton of heritage brands are making top-notch swimwear that perfectly splits the difference between fashion and functionality. If you’re feeling bold, we recommend these whimsically patterned shorts from the outdoor experts at Patagonia. And if those are too strong for your taste, they also come in a stately Viking Blue.

Minimalism looks good at the beach. A simple black swim trunk, cut on the shorter side so that it hits just above the knee, is always a class act. We love this version from surf king Saturdays, which comes equipped with plenty of pockets for stashing your wallet and other goodies once you’re back on land.