First, choose basic pieces in neutrals or versatile black-and-white prints. Then, add a few key accessories like a day-to-evening clutch, a strand of pearls, or a pair of great shoes. Finally, finish with a matte red lipstick and you are ready to wow.
Philip Lim for Nars limited edition nail varnish, in Shutter, $20, available at Bluemercury | Velvet by Graham Spencer shearling vest, $180, available at Valentina, Lake Forest, 847-535-9600 | Sarah Chloe gold-plated nameplate pendant, $306, available at Valentina | AG Adriano Goldschmied denim, in tan, $168, available at Lillie Alexander, Lake Forest, 847-295-8686 | Tory Burch knit dress, in dotted pony print, $395, available at Lillie Alexander | Ischiko cozy sweater, in nocturn blue, $669, available at Oska, Lake Forest, 847-482-1650 | Bobbi Brown lip color in Red #10, available at available at Bluemercury | Sam Edleman leopard print booties, $164, available at Forest Bootery | Kate spade low pumps with embellished heel in black patent leather, $398, available at Lillie Alexander, Lake Forest | Basler reversible pale rose/floral print jacket, $674, available at the Lake Forest Shop, Lake Forest, 847-234-0548 | Joie knit jacket with leather trim, $398, available at Lillie Alexander, and Oska pencil skirt, $189, available at Oska | Maps Collective genuine crocodile clutch, $1,150, available at the Lake Forest Shop | Oska wool vest with leather closure, in charcoal grey, $369, available at Oska | Nars limited edition Smokey Eye kit, $59, available at Bluemercury, Lake Forest, 847-847-615-3000 | Joseph Ribakoff jacket with zips $300, available at The Lake Forest Shop, Lake Forest | Hunter Boots in dark olive, $148, and Hunter cable knit fleece welly socks in grey, $45, both available at Forest Bootery, Lake Forest, 847-234-0201 | Sarah Campbell houndstooth peplum top, $158, available at Sarah Campbell, Lake Forest, 847-234-6416 | Lands Downunder Italian herringbone throw, $128, available at Valentina
– Alicia Foley