For a while, it seemed like men’s shorts got shorter, slimmer and tighter every summer. Thankfully, those days are behind us. Today’s best pairs have a little more room to breathe, borrowing their proportions from relaxed tailoring with fuller legs, deeper pleats and hems that hit just above the knee. The result feels smarter, cooler and, most importantly, a whole lot more comfortable when the temperatures start climbing.

The pleat is what makes the difference. It gives the shorts shape and movement, creating an easy drape that elevates even the simplest outfit. Throw on a tank top and loafers, a breezy linen shirt or even a knit polo, and suddenly your warm-weather uniform looks a lot more considered instead of just casual. We tried on a range of options to find the best pairs that get the fit, fabric and proportions just right—no matter your budget.