On a Saturday morning a couple of months ago, a New York magazine reporter, vintage store owner Greg Armas and myself were in line at the Upper West Side Goodwill at 9 AM. Some people had been posted in front of the store since 4 AM that morning, anticipating a huge deal on one of the new designer arrivals. (Did they not know most of it was fake?) Greg and I geared up to complete our challenge: spend $100 on as many items as possible that could be resold at better value. As soon as the clerk opened the door, we rushed in and went on our mission. I think we both did really well in the end. We both spent our money wisely on classic, timeless pieces. And we got to keep them too!