Creative director, gallerist and raconteur Andy Spade invited filmmaker Alison Chernick to his Southampton family residence for an anecdotal overview of his high-low artworks. The light-flooded 19th-century house was originally the site of the Shinnecock Hills Summer School, a plein air painting academy run by William Merritt Chase, founder of Parsons. But Spade and his wife Kate, with whom he created preppy handbag empire Kate Spade and its men's offshoot Jack Spade (both sold to Neiman Marcus in 1999), have transformed the space into a showcase for their cache of treasures—from a rare Tony Alva skateboard to an original René Ricard to faux Picassos to model airplanes, picked up in flea markets across the country and through friends including Julian Schnabel. Ask him for his favorite hunting grounds and beyond the obligatory Paris, New York and Morocco mentions,  he'll note less obvious locales: "Kansas City for gems; Tucson, Arizona for Native American arts and crafts." The range is testament to Spade’s emotion-driven collecting philosophy, which extends to his gallery-cum-design studio with Anthony Sperduti, Partners & Spade: The NoHo headquarters serve as a base of operations for the pair, who design ads for the likes of J.Crew, with the building's storefront playing host to exhibitions spanning a menagerie of vintage globes to a Glenn O'Brien-curated group show featuring pieces by Richard Prince and Robert Hawkins.