Sperry Top-Siders is a brand of shoe that has been around for eighty years. The sole of a Sperry Top-Sider grips when wet making it unlike other shoes. These ads drop the “Top-Sider” appellation. They seek to go beyond the Sperry product difference and to associate Sperry with a feeling.
Sperry communicates that feeling by telling readers about the people who wear Sperry. Product users are a wonderful means of communicating feelings because product users are have broad implications. We infer a lot about a brand from the people we believe use the brand. We expect we can feel like those users if become users ourselves.
In this case, we learn that people who wear Sperry are young, attractive, active, adventurous, and, probably, well-off. We infer that the shoes are for that sort of people so the shoes must be fashionable, high quality, and hip. Whether we have a boat or not, if we want to feel young, attractive, active, adventurous, and well-off, we should wear fashionable, high quality Sperry.
Of course the ad doesn’t literally tell us who wears Sperry or how we will feel if we wear Sperry. Advertising works by leading receivers to a conclusion, not by stating a conclusion that receivers would likely debate.