We were in the middle of an epic heat wave while I was brainstorming ideas for our November style shoot, and the intense humidity was making me lazy. I only had energy to sweat. With our shoot date looming, I needed to come up with a concept. I grabbed a stack of fall/winter lookbooks to flip through for inspiration, but looking at models in heavy coats, thick sweaters, and knee-high boots nearly gave me heatstroke. What struck me was the contrast between life here in Los Angeles and the models on the page. Here I was sitting under the shade of an avocado tree, barefoot and in a bathing suit; those women were so bundled up. They reminded me of the frigid New York weather during Fashion Week last February—the brutal wind, the relentless snow—and I suddenly felt grateful for the heat, however hellish. Yes, we’re pretty lucky in the land of eternal sunshine. I tossed the fall/winter lookbooks aside and reached for cruise/resort ones instead. The latest collections would look right at home here in L.A.—and practically all year long. The retro vibe that weaved through the collections I revisited made me think about LA.’s go-to getaway: Palm Springs. Swooning over the clothes, I pictured a glamorous woman on a glamorous vacation, impeccably dressed, with an aloof air that made her all the more mysterious. She would turn heads wherever she went. I pictured her at The Parker Palm Springs. The luxury hotel—with its green croquet lawns, lush gardens, and luxurious pools—would provide her the perfect backdrop. I had my idea.
I immediately began pulling clothes (Naeem Khan caftans, Fendi culottes, JC de Castelbajac jumpsuits) to match the various vibes of Palm Springs through the decades (which the hotel’s eclectic decor also does): a mashup of sleek midcentury modern, ’60s glam, and ’70s groovy. The best part? Michelle Monaghan was available to star in our shoot. I’ve been a fan of the actress since I first heard her raspy voice in Kiss Kiss Bang Bang. I loved her in Gone Baby Gone and, of course, in True Detective. She’s also one of the nicest and most easy going and unaffected actresses I’ve worked with, and proved to be one of the easiest to style. She looks stunning in everything. Before we began shooting, Monaghan asked me for a little direction. I hadn’t yet put my concept into words, but told her, “You’re a rich bitch on vacation.” She laughed and said, “I can do that.”