Knowing that Trunk Club’s ideal customer is a man who hates shopping, and also knowing that one of its biggest differentiators is having a personal stylist—a big cognitive leap—we recognized an opportunity to address any potential hesitance directly in the commercial. We strove to not only address that hesitation, but flip it on its head and turn it into a positive, into a moment of personal growth in a long line of decisive moments—some big, some small, all nostalgic—that have lead us to this very moment.

In the commercial you witness some archetypal turning point moments in a man’s life—the first time he glimpsed a Playboy magazine, his first sip of whiskey, the moment he was handed the keys to his first car, and, finally, that feeling of confidence when you show up to a date knowing you look good.