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What If They Were…

Photos by Spencer Brown

Take happiness, success, self-confidence out of the equation. Everyone, at some point, has wanted to be somebody else, or imagined themselves living a completely different life. Wouldn’t it be nice to trade places, even for a day, with Cindy Crawford, Thomas Keller or Lin Manuel Miranda? We asked fashion designer Karen Caldwell to choose her aspirational alter ego, and she picked Iris Apfel. Prima ballerina Yuan Yuan Tan channeled In the Mood for Love star Maggie Cheung, and Robert Mailer Anderson exuded world-weary gravitas as literary detective Sam Spade. Last but not least, Dede Wilsey, a generous supporter of the arts, took on the role of artist— paint splatters and all! In our feature,“What If They Were…,” we reimagine these Bay Area luminaries as their bizarro selves: a private eye, a painter, a movie star and an incredibly chic gardener.

Karen Caldwell… as the master gardener

Photo: Spencer Brown; hair and makeup: Toni Rigdon.

The St. Helena designer, known for her effervescent personality and glamorous vintage gowns, grabs a pair of garden shears and makes it fashion. Here, she pays homage to nonagenarian style icon Iris Apfel, famed for her irreverent, must-have clothing and accessories. “She’s my hero!” says Caldwell. “If I live to be 97 years young, I want to still be rocking out my style as beautifully as she does! Never too old to keep playing dress-up!” Caldwell, who’s got an extraordinary collection of retro baubles, imagines she and Apfel becoming instant friends. “If I were to have drinks and dinner with Iris, I believe we would both choose Campari and soda,” she muses.“Rumor has it that it’s Iris’ favorite, plus she often asks the bartender to bring the ingredients to her so that she can concoct it herself! DIY. We would discuss at lengthour shared love of all things vintage costume statement jewelry. We would laugh a lot, as we both love humor, and I bet I could talk her into letting me try on her amazing Lucite bangles, and of course those fabulous oversized vintage glasses!” Continues Caldwell: “I really do see myself having the same approach to my life in my later years, as Iris. Getting older has never bothered me. It’s all in the way you look at the world, and I choose to look at it positively and to forever take the happy path, and fill it with color and joy!”

Yuan Yuan Tan… as the film actress

Photo: Spencer Brown; hair and makeup: Maya Roget. Additional wardrobe support provided by Saks Fifth Avenue.

“I have loved Chinese design, Chinese qipao, since I was little — it’s part of my country’s culture,” says Tan, the prima ballerina at San Francisco Ballet, who wanted to pay homage to the 2000 romance In the Mood for Love, starring Maggie Cheung and Tony Chiu-Wai Leung. “I love the director Kar-Wai Wong, and I love [Cheung] — she’s like my all-time favorite actress, besides Audrey Hepburn. … I just like watching her portray all kinds of characters. She’s phenomenal, especially [in] In the Mood for Love. I just love way she handled all the details.” For her glam Gazette photoshoot, Tan, who was preparing to dance the title role in The Little Mermaid, to be staged April 19 through April 28, wore a stunning Blanc de Chine dress from her own closet, accentuated by sparkling, Hollywood starlet-caliber jewels by Shreve & Co.

Dede Wilsey… as the impressionist painter

Photo: Spencer Brown; hair and makeup: Maya Roget. Additional wardrobe support provided by Saks Fifth Avenue.

“It was great fun to dress as an artist and not have to be in a business suit,” says Wilsey, the irrepressible San Francisco socialite and arts benefactor, often seen in pristine, oh-so-appropriate Chanel suits and Oscar de la Renta dresses. “I really was longing to make a great big mess, and probably paint myself — by that, I mean paint my apron.” If Wilsey could be any style of painter, “I would like to be an impressionist artist because I would like to want to hang what I painted.” Monet and Magritte are among her favorite artists, and she loves surrealism (“I think it would be so much fun to set up some kind of really weird surrealist setting”). Wilsey, the devoted owner of a gaggle of Maltese, recalls singer Tony Bennett once revealing to her that he’d “painted a painting where the clouds were Maltese dogs.” Quoth Wilsey: “Now that would be fun to paint.”

Robert Mailer Anderson… as the noir detective

Photo by Spencer Brown.

When Mailer Anderson enters a room, he fills it with his larger-than-life presence: On a recent March afternoon, he arrived at our studio dressed as though he’d just stepped out of a page from Dashiell Hammett’s 1930 novel, The Maltese Falcon, completing the shadowy Sam Spade look with a noirish hat, suit, trench coat, in addition to the been-there, seen-it-all expression. (We provided the fog machine.) The acclaimed novelist, screenwriter, playwright and philanthropist, married to Nicola Miner since 1999, restored the former apartment of Hammett and his fictional alter ego, Spade, at 891 Post Street, to resemble what it would have been like to live — and write — there circa the 1920s. Mailer Anderson, who wrote his 2001 debut novel Boonville in a single-room-occupancy unit in San Francisco’s North Beach neighborhood, recently premiered Windows on the World, a drama he wrote and produced, at the Sedona International Film Festival. It stars Edward James Olmos as a father who leaves Mexico to find work in New York City, where he lands at the World Trade Center’s Windows on the World restaurant. Following the September 11 attacks, his son (portrayed by Ryan Guzman) journeys to Manhattan to find him.

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