Avoid '80s-reject territory with simple boots and a smart tweed jacket.
(top to bottom) Wool-acetate (safety pins not included) jacket, IRO, $731; 212-691-1905. Cotton jersey T-shirt, Chinti and Parker, $115; chintiandparker.com. Sterling silver ring, Alberto Juan, $170; endless.com. Denim jeans, Guess by Marciano, $178; guessbymarciano.com. Suede ankle boots, Joan & David, $260; at select Bloomingdale's stores.Read MoreLess