Severely Sexy: Go for hard-edge leather biker separates, macabre jewels and, of course, an irresistible Alex Wang motorcycle helmet.
Pierre Balmain Jacket, $1,640, nordstrom.com; Sweatshirt, $18, H&M, 212-489-0390; Jean Paul Gaultier Top, $695, Neiman Marcus, 310-550-5900; Pant, $495, Alexander Wang, 212-977-9683; Necklace, $395, johnhardy.com; Boots, $115, drmartens.com; Helmet, price upon request, Alexander Wang, 212-977-9683; Eddie Borgo Cuff, $440, Bergdorf Goodman, 888-774-2424; Theyskens' Theory Backpack, $575, Theory, 212-524-6790
Breathlessly Beautiful: Emulate Ms. Monroe's effervescent glamour with '50s classics, rollered hair and an ever-red lip.
L'Wren Scott Dress, $2,680, barneys.com; Selima Sun for J.Crew Sunglasses, $128, jcrew.com; Sweater, $30, Uniqlo, 877-486-4756; Scarf, $10, luxurydivas.com; Dolce & Gabbana Lipstick, $34, saks.com; Sandal, $690, Fendi, 212-759-4646; Pant, $248, Steven Alan, 212-343-0692; Victoria Beckham Tote, $3,750, net-a-porter.com
F. Martin Ramin for The Wall Street Journal, Styling by Anne Cardenas and Elizabeth Osborne; Poster: The Weinstein Company/Everett Collection
Pantomime Pretty: Conjure the style of silent films with black-and-white pieces with ornate Art Deco details.
Black Pleated Dress, $10,500, gucci.com; DAY Birger et Mikkelsen Cape, $250, net-a-porter.com; Necklace, $68, anntaylor.com; Chemise, $550, aridein.com; Bag, $170, Whiting & Davis, 800-827-1112; Pump, $295, Tory Burch, 212-510-8371; Jennifer Behr Barrette, $198, saksfifthavenue.com.