An idea of the breadth of beverages offered

Holding an outdoor event in Chicago in September is a gamble, and Saturday night's weather didn't exactly agree with the 16th annual Green Tie Ball, which took place for the second year at Northerly Island’s Charter One Pavilion. It's hard to rock black-tie attire and keep warm when the temp is hovering around 50, but I planned accordingly and opted for black-tie casual: tuxedo pants and a cream silk camisole under a cropped pea coat and Missoni scarf. (Attending the event relentlessly for the past six years should have taught me something.) Other female guests didn’t fare so well. "I was shaking a lot," said one friend who braved a dress.

Despite some glitches—like a short fireworks display; apparently the control guy had the firecrackers facing the wrong way, and sparks were flying into the pavilion—the night was a success, with 3,000-plus guests raising more than $250,000 for Chicago Gateway Green, a non-profit that helps beautify the areas alongside Chicago’s expressways. Even 90210 and Dancing with the Stars alum Ian Ziering put in an appearance, as did actor Michael Pena (World Trade Center, Babel, Crash), and local reality-TV hunk Wendell Jisa from the Jen Schefft-era Bachelorette.

If you didn’t make it this year but are considering a future drop by the ball, read on for a list of Green Tie dos and don’ts. Hey, someone else should benefit from my six years of dedicated field study.

DO:

That's me and Chicago Sport and Social Club president Jason Erkes, also a long-time attendee

Dress appropriately. No one will kick you out for being underdressed. Or make your way to the Horseshoe Casino tent, which is usually packed and heated.

Arrive on time. The food was scarce by the time we showed up at 10 p.m., maybe because there were only 60 restaurant booths this year (Avenue M, Rockit, and Gibsons, among them) compared with 100 last year. Last Girl Standing didn't have a bite to eat, and neither did my party posse, which made for seven killer hangovers the next day.

Wear comfortable shoes. There's nowhere to sit, unless you want to hang out in no-man's land. You'll be walking a lot and dancing a lot, and no one cares what shoes you're wearing when he’s this drunk.

Make a point of meeting new people. This is one of the best singles events of the year for twenty- through fortysomethings. If you don't bring a date, there’s a pretty sure bet you'll find one here.

Dodge Your Ex. GTB should be called DYE. (My group bumped into at least three former flames. Yikes.)

DON'T:

Drink beforehand. There's plenty of alcohol to go around, and you've already paid for it ($120 for general admission; $250 for VIP access—which doesn’t amount to much more than general admission), so you might as well get your money's worth.

Don't forget to tip your friendly bartender.

Line up a limo. GTB organizers hire free trolleys to take guests downtown, where cabs are plentiful.

Be the drunkest person there. Everyone's taking pictures, and you never know whose online gallery you'll end up on. Trust me on this one.

Forget to tip. The ball’s bartenders are volunteers who give up their regular Saturday-night gigs to work the charity event, so be friendly and tip well. Especially if you want a strong pour.

Give your number out to just about anyone. Enough said.

Photographs courtesy of Sarah Preston