Altuzarra Jessica Blanket-Striped Dress, $1,169, at matchesfashion.com; Michael Kors Wool-Gabardine Trench Coat, $3,295, at net-a-porter.com; Gianvito Rossi Suede Cuissard Boots, $2,195, at Barney's; D2 Babe Wire Clutch, $725, at dsquared2.com