The heat of summer presents a man with a whole slew of style challenges. Here are five sultry situations and tips for finding shelter from the swelter:

Take the Beach
"If you wear swim trunks with an elastic waistband, they'll bunch up around your waist, which can overemphasize love handles," says Richard Battaglia, director of sales for Robin Piccone Swimwear. Those attractive red compression marks around your hips really drive the women crazy, don't they? Instead, look for boxer-style trunks that button around the waist. Knee-length surfer shorts are hip, but they'll make you look shorter than you are, so avoid them if you're under 6'2''.

Conquer the Clambake
In anthropological terms, the company barbecue is a fascinating event, as corporate cronies attempt to look casual while jockeying to be the CEO's partner in the three-legged race. It's almost impossible to look relaxed yet responsible. Our secret: crisp khaki shorts (no pleats; they make you look fat) and a color-coordinated short-sleeved button-down. Tan shorts with, say, a black or red top looks casual, yes, but the same shorts with an olive or a blue-and-tan top looks laid-back and hints that you're still in uniform.

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Wear leather on your feet. (No socks, please!) If you wear running shoes with shorts, you might as well say, "I've got a pocketful of Vicodin; meet me behind the beer truck."

Wow the Wedding
Your man, Chopper, is getting married at last—outside, in Atlanta, in July—and you're pretty sure the invite said, "no cutoffs." If it's evening, a suit is a must, says Butcher; for an afternoon wedding, you can get away with a navy-blue blazer, pressed khakis, and a tie. Think light-colored cotton or summer-weight wool (light-colored linen is too casual for wedded bliss, even if doing the Electric Slide and the Chicken Dance is mandatory).

And under no circumstances—even if it's hot, even if you're cranky, even if every carbon molecule of your being is commanding you to stand up and cry, "My God, stop this madness!"—should you take off your jacket during the ceremony. Save that move for when you're dancing with a bridesmaid who has a taste for chardonnay.

Stay Cool at the Summit
If you've got an important meeting and humidity is high, remember, the fabrics that will keep you coolest are linen, cotton, and summer-weight wool, in that order. Unfortunately, they'll wrinkle in that order, too. Here's the simple style rule of thumb for summer meetings: If you're popping in and popping out, choose linen or cotton. But if it's an all-day affair that's going to force you to look both fashionable and focused for hours at a time, go with the wool and stay in the A/C. Darker colors like blue, black, and olive show perspiration the least. And make sure your socks are mainly cotton, says Butcher; they'll keep your feet cool even if the rest of you is taking heat.

Here's a summer style tip: Bring a box of laundered shirts to your office and slap on a fresh one right before the big meeting. If you wear T-shirts, keep a fresh, clean white one on hand. Plain white—not the one you got at the KISS farewell tour.

Seize Social Advantage
When ice starts tinkling in tall glasses, the conversation should be bright, light, and buoyant. No diatribes on foreign currencies, no rants on how Pinella is mismanaging his bullpen.

And don't highlight the fact that while all your trust-fund buddies were hanging in the Hamptons, you were working your self-made-man vibe under the fluorescents. "If you haven't got that summer tan, a nice long-sleeved T-shirt or linen shirt and khakis will keep you looking summery and successful, even if you're a pale rider underneath," Butcher recommends. (Remember, horizontal stripes are for thin men only.) A light-colored sport coat will show off how well business has been treating you.

Next time some bore has you trapped, tell him there's somebody you'd like him to meet and escort him over to your buddy across the room. Once the circle of tedium is broken, you may be able to make a gracious getaway and prowl the party.