The Crush Cowboy boots and cannonau may not be a common pairing. But Aaron Epstein —who counts a pair of size 16A (!) custom-made Anderson Beam sharkskin boots among his prized possessions—is no conventional wine snob. “I have a bumper sticker that says, ‘I don’t hang out with people who drink 100 point wine,’” says Epstein, the New York transplant crushing S.D.’s wine scene with Le Metro (lemetrowine.com). The 1-year-old monthly subscription service is a cult sensation, thanks to Epstein’s eclectic bottle curation and Le Metro’s liner note-inspired tasting notes, custom illustrated by famed blogger Elaine Chukan Brown. “I’m taking people out of Napa cab land, but I’m cushioning the journey,” says Epstein, who lives steps from the ocean in O.B. with his wife and their newborn son, Micah. There, his boots share closet space with a case of Vesper Vineyards rosé. “Our house wine,” jokes Epstein, whose expertise and insight into small releases and boutique wines recently landed him in The Washington Post . “The vast majority of the wines I’m getting cannot be reordered,” he notes. An example: Enfield Wine Co.’s 2011 Haynes Vineyard Syrah, which recently starred in a six-bottle collection themed Seduced by Syrah. Also exclusive? His handmade suits (all in neutral colors so his blue Warby Parkers pop) from Thailand, and custom shoes by Piero Calzature in Bologna, where trilingual Epstein lived and first fell in love with vino. “Try finding a 16A in the shops!” OUTFIT White dinner jacket, $3,630, and pink floral tie, $240, by Tom Ford; tuxedo shirt, $285, by Eaton; trousers, $225, by Theory; shoes, $475, by Magnanni, all at Neiman Marcus, Fashion Valley.