What can you learn about a stranger on the street in under five minutes?  What are the best ways to begin a conversation with someone that could lend itself to more in-depth interviews, or quickly establish a small amount of trust interviewer and interviewee?  In this experiment, we find that asking strangers about what they are wearing is an effective and surprisingly intimate way to begin a dialogue with strangers on the street.  We further reflect on the methodological and creative issues which arose during the editing and presentation of this inter-discplinary collaboration.