When two objects collide they leave evidence of their mashup on each other; cars swap traces of paint, and a run-in with Moira Kelly left DB Sweeney covered in Lycra. For a collision of preppy and pop, try Drukker Enterprises
From a self-described NY preppy who'd grown weary of his friends wearing the same button-downs every night, Druk hawks prepped up tees and dressed down sweaters that converge on a vibe of puckish rebellion.
Tees're covered with moneyed society references, like Clubhouse's crossed golf clubs, Stargyle's pink/black/grey argyle print, and the Kennedy/Monroe photo montage on Play Like a President (a reference to the plaque hanging in Kennedy's locker room that he used to slap before sleeping with actresses).
As for sweaters, Druk's hawking rad merino v-necks casualed up with pop imagery, like the 80's$ (pink w/ b&w Corvette and Lambo silhouettes), the Princeton (oddly, a vintage Detroit Tigers graphic), and Here's Johnny -- a colorized photo of 80s-era Jack Nicholson, carelessly smoking as if certain he'd be alive in twenty years
Druk also offers a few pieces that veer single mindedly prep or pop, like a dark blue polo w/ logo on the placket, and a black tee emblazoned w/ a luxuriating woman in panties and the message "Air Conditioning and Birth Control (all you really need)" -- for when you want to leave nary a trace of your own dastardly collision.