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"I see Shepherd & Sims as an upscale but approachable fine-dining spot from Jim and Angelique Stump; its name is a mashup of their former last names and the menu comes from the kinds of meals they love to share. The menu veers from pickled fried green tomatoes with buttermilk dressing to a 45-day dry-aged New York steak, and Jim partnered with chef de cuisine Robert De La Mora to create a California-ingredient–forward menu infused with global flavors — an al pastor-inspired pork chop crowned with pineapple puree, Yukon potatoes with a kombu butter accoutrement, and even caviar, pate, and ratatouille. They stress they don't want the restaurant to feel inaccessible — Jim says he wants to have caviar on a Tuesday afternoon — and intentionally opened in an underserved part of town rather than downtown Los Gatos. The beverage program is a family affair, with their son running the cocktail program (including two to three cocktails on draft) and their daughter curating a wine list that skips the usual California chardonnay and cabernet in favor of selections from lesser-known regions; the back bar showcases everything from Absolut and Patron to Pappy and Weller, and you can order anything from a beer and shot to a crystal-clear cube of ice for your whiskey. Designed with Arcsineto, the space blends a French bistro aesthetic with the warmth of a New American neighborhood restaurant — a towering mural of a cat eyeing colorful birds in the entryway, a black-and-white ampersand mosaic embedded in the floor, a gallery wall of family photos and memorabilia, walnut and stone textures and a mural of the nearby Santa Cruz Mountains, plus antique mirrors and beadboard — and it's open Wednesday through Sunday for happy hour and dinner." - Lauren Saria