On the Cover: Photograph by Bobby Doherty for New York Magazine. Styling by Rebecca Ramsey. Silk boatneck gown with detachable dégradé pearl Watteau by Lela Rose, $4,995 at Gabriella New York, 155 Wooster St.; 212-206-1915. Diamond engagement ring set in platinum, price upon request, and cultured-pearl necklace with 18-karat-gold clasp, $34,000, both by Tiffany & Co. at tiffany.com. Hair by Linda Shalabi using Oribe at See Management. Makeup by Allie Smith using Nars at Sarah Laird. Manicure by Roseanne Singleton using Dior Vernis at Art Department. Clooney ranunculus from Stems Brooklyn. Market editing by Lori Keong. Model: Erika Pattison at Marilyn Model Management.