In January 2013, Richard Ross stood outside a drab brick building in Pawtucket, R.I., a fashion pilgrim drawn to an unlikely mecca. Months earlier, Mr. Ross had learned of a designer there named Kiel James Patrick, or KJP for short, who promotes his line of nautical-inspired bracelets and other apparel robustly through social media.

Mr. Patrick’s favored medium is Instagram. In a stream of elaborately staged shots and off-the-cuff selfies, he documents the many splendors of a certain strain of New England life: sipping mimosas at the Head of the Charles Regatta; piling into a Jeep Wagoneer; organizing an Izod shirt collection. The KJP factory in Pawtucket makes frequent appearances. So does Mr. Patrick’s fiancée and business partner, a petite Jackie Kennedy-styled brunette named Sarah Vickers, along with a nattily dressed gang of 20-somethings, presumably the couple’s friends.

For the KJP crew, every season presents a photo op. Winter finds them at a Maine ski lodge. Summer brings bonfires on the beach and a “Gatsby” dress-up party at a private waterfront club in East Providence, R.I. For their engagement photo, Mr. Patrick and Ms. Vickers posed in front of an Irish castle, fireworks bursting in air. Part Camelot 2.0, part junior Ralph Lauren, the world Mr. Patrick has created is both ridiculous and highly compelling.

Mr. Ross, a theater major at Baylor University at the time, studied the photos, intrigued by the people who appeared in them. Were they really friends? Did they own these incredible houses? Were they rich kids? Was Kiel James Patrick even his real name?