This season’s conversation print at Rachel Comey is a raffle ticket stamped with the words GOOD TIMES. She also blew it up to supersized proportions, so big the effect was almost abstract. None of these pieces made the lookbook, but the sentiment suffuses these resort clothes. Comey has made herself a wardrobe staple for the creative classes from New York to Los Angeles not by making everyday staples, but by adding a dash of the offbeat and eccentric to those everyday staples.

If these photos bring Little Edie at Grey Gardens to mind, that’s not entirely accidental. They were photographed in Gertrude Vanderbilt Whitney’s ceramics studio in Roslyn, New York. (Vanderbilt Whitney was the founder of the Whitney Museum of American Art.) “It hasn’t been touched,” Comey marveled of the studio’s mosaic stone floors, wall murals, and empty kitchen cupboards. “In that way it is very like Grey Gardens.”

Naturally, there’s an air of the art-loving iconoclast to the clothes. See the opening look’s clashing intarsia knits and country club-ish 1980s embroidered corduroy shirt, the seafoam green gown worn with a brushed mohair man’s coat and bedroom slippers, or the printed and pintucked blouse tucked into a long narrow skirt with perma-creases, complete with a rhinestone brooch pinned to the waistband.

Comey’s signature—or one of them, at least—is the way she marries the “nutty, novelty” detail with the eminently wearable. This season’s exemplars are the quilted barn jacket and car coat with the deep detachable faux fur muffs at the wrists. A shearling jacket with gold polka dots, like someone had daubed it with a paintbrush, was a surprise sell-out last year; this season’s update is a curly-haired shearling with ribbed knit collar and sleeves.