Final answer:
In The Office S6E19 "Happy Hour," Michael Scott transforms into "Date Mike" after turning his baseball cap backwards, which is marked by his wearing of a Kangol hat.
Step-by-step explanation:
In S6E19 "Happy Hour" of The Office, the clothing item that transforms Michael Scott into "Date Mike" is a Kangol hat. When he realizes that the bar scene is more casual than he anticipated, he turns his baseball cap backwards, which marks the transition from Michael Scott to his alter ego, Date Mike, who he warns is "nice to meet, but bad for business."
This transformation is meant to be humorous, capturing Michael's quirky and often misguided understanding of what it means to be suave and appealing on a date.