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1. From left: Jacket in Nero cotton and silk smoking twill, $3,650, and pant in Nero cotton and silk smoking twill, $1,440, both at Bottega Veneta, Westfield Valley Fair; bodysuit, $185, at falke.com; Rejane Opera in Black Box calf leather, $3,400, at moynat.com; gold skinny flat-plate choker, $195, at jenniferfisherjewelry.com; Alhambra ring, $235, and Alcazar ring, $145, at aureliebidermann.com. Heavy double-faced wool jacket, $3,520, and heavy double-faced wool pant, $2,290, both by The Row at Neiman Marcus, Stanford Shopping Center; white cotton dress shirt, $1,250, by Fendi at Saks Fifth Avenue, San Francisco; Cinhetic bag, $5,350, at hermes.com; Pennies from Heaven earrings, $440, at attling.com.
2. From left: Power jacket in Graham, $585, and HW pleat pant in Graham, $455, both at theory.com; cashmere long-sleeved turtleneck sweater, $695, and calfskin belt, $185, both at Max Mara, Stanford Shopping Center; Jacno camel loafers, $595, by Pierre Hardy at ssense. com; long classic gloves, $500, at jilsander.com; Roulis mini bag, $6,850, at hermes.com. Angela blazer in scarlet red, $1,595, vest pant in scarlet red, $1,095, and Steinem turtleneck in red, $595, all at gabrielahearst.com; double-buckle leather shoes, $650, at santonishoes.com; Thalia Cocktail handbag, $1,150, by Salvatore Ferragamo at Bloomingdale’s, Stanford Shopping Center; Sans pavé curved bar necklace, $1,050, at paigenovick.com; gold 2.5-inch Samira hoop earrings, $550, at jenniferfisherjewelry.com.
3. De Gaulle TM jacket, $2,910, Darleen top, $670, and Dexter pant, $1,520, all at jilsander.com; shoes, $595, at church-footwear.com; Cinhetic bag, $5,350, at hermes.com; black Pioneer calf leather eyelet belt, $765, at alexandermcqueen.com.
4. Double-breasted blazer, $1,895, classic straight-leg pant, $895, Stocking top, $1,075, and Western boot, $1,295, all by Calvin Klein 205W39NYC.
5. Jacket in navy wool felt, $2,850, trousers in navy wool felt, $1,600, and shirt in white featherweight leather, $3,250, all at Céline, San Francisco; Richard earrings, $6,400, by Ana Khouri x Narciso Rodriguez at barneys.com; Jacks split-sole slip-on white lizard embossed calf shoes, $325, at newbark.com; Fetiche long clutch, $1,790, by Saint Laurent by Anthony Vaccarello at ysl.com.
6. Cashmere jacket with leather detail, $5,720, and cashmere wide-legged trousers, $2,545, both at alexandermcqueen.com; dark forest-green/gold mirror crocodile Origami flap clutch, $2,350, at nancygonzalez.com.
7. From left: Prince of Wales jacket, $2,495, and Prince of Wales straight-leg pant, $1,195, both at jasonwustudio.com; cashmere long-sleeved turtleneck sweater, $695, at Max Mara, Stanford Shopping Center; Peaked collar in 12K gold vermeil, $250, at eddieborgo.com. Boycott jacket, $1,995, and Boycott pant, $1,695, at ellery.com; Gathered shirt, $550, at protagonist.com; bone Janelle pump, $675, at bally.com; Sans pavé large sculptural single statement earring in 18K gold, $1,030, at paigenovick.com; Envelope in nude patent leather bag, $1,300, by M2Malletier at chalkboutique.com.
8. Wool double-breasted jacket, $1,250, and wool wide-leg pant, $745, both at Max Mara, Stanford Shopping Center; silk bias top in stone pink, $245, at theory.com; Boything shoes, $425, at Stuart Weitzman, Stanford Shopping Center; Desert Rose crocodile clutch, $10,900, at Bottega Veneta, Westfield Valley Fair; gold Overlap Script ring, $295, at jenniferfisherjewelry.com.
9. Navy blue wool rounded-sleeve jacket, $1,900, Klein blue embroidered hooded knit sweater, price upon request, and navy blue wool pleated trousers, $1,900, all at delpozo.com; shoes, $595, at church-footwear.com; chocolate Christy python clutch, $2,150, by Michael Kors Collection at Michael Kors, Westfield Valley Fair; Twosome ring in 18K yellow gold, $3,100, Wide & Signature ring in 18K yellow gold, $4,100, and Moonwalk ring in 18K vermeil, $350, all at attling.com.
Originally published in the September/October issue of Silicon Valley