UPDATE: This story was originally published on August 27.
Let's face it: First impressions matter. That said, there's a lot of pressure on most first dates. In addition to the fear of whether or not our effervescent personalities will shine through and the apprehension over the perfect meet-up spot, there's the all-important question of what to wear.
Instead of calling an emergency girlfriend session, we went out and got advice straight from the source. We've asked six so-charming Chicago guys (from a master mixologist to a Chicago Fire player) to dish on surefire outfits guaranteed to capture their attention — and we were pleasantly surprised. Here's a hint: It's not all about slipping on sky-high stilettos. So, whether you dress for yourself, your friends, your date — or most likely, something in between, click through. After all, if you get a little help with your outfit-planning, you can spend your energy on more fun things…like planning the perfect second date.