Event: Macy's Glamorama 2008: Pop Candy Arcade
Crowd: Mini-celebrities, fashionistas, media types
Why You're Going: One word: Models. And not just the leggy ones you've arrived with. Plus, you'll want to see if this year's talent, MC Hammer and Cyndi Lauper, actually manages a duet.
Benefits with Friends
Chicago Fall Formals
You look damn good in that tux. But with your fall charity benefit RSVPs piling up, the tricky part isfiguring out where to display it. Put these five galas on your don't-just-send-a-check radar.
Event: Lovely So Real, the Renaissance Society Gala and Auction
Crowd: Edgy art lovers, design-industry peeps
Why You're Going: It's like MCA's First Fridays with better booze. Plus, while art speculators are looking for a steal at the silent auction, you'll have a chance to work your own kind of artistry on that young gallerist you've been eyeing.
Event: Green Tie Ball XVII, benefiting Chicago Gateway Green
Crowd: Pretty young things clad in creative spins on the green theme
Why You're Going: You have a knack of getting lucky at these things—and now you can double down James Bond-style at the Horseshoe Casino gaming tent, which promises to be the highlight of this year's 3,000-person-strong affair.
Event: The Modern Ball in the Modern Wing
Crowd: People who hang Picassos in their bathrooms
Why You're Going: This is history in the making—the first chance to view the Renzo Piano-designed Modern Wing. But you may want to play it cool until Nov. 8 when the Auxiliary Board hosts a gala with a crowd promising to be, shall we say, a bit more modern.
Event: Top Chef Chicago, a benefit for chef Art Smith's Common Threads
Crowd: Not-too-serious foodies
Why You're Going: The food at this event is the only thing strictly black tie, so you can give that tux a night off. With an all-star Top Chef lineup, you'll be sated. In the kitchen: Stephanie Izard, Dale Levitski, Dale Talde, Lisa Fernandez, Valerie Bolon, Spike Mendelsohn and Sara Nguyen.