The Wardrobe: Karen Caldwell

Story By Natasha Chalenko | Photos By Margo Moritz

Karen Caldwell is a celebrated Bay Area fashion designer known for her Old Hollywood-style, ultra-glamorous red-carpet standouts. Sophisticated, feminine and flattering, with the seductively nostalgic allure of vintage, her custom-made creations won the hearts of Jessica Chastain, Viola Davis, Helena Bonham Carter, Annie Lennox and Diana Ross. Caldwell’s virtuoso creations and unparalleled vintage costume jewelry collection are featured in numerous TV shows and movies, including Oscar nominee The Help.

She’s also the go-to designer for San Francisco society stars who want to look fabulous—whether at a gala ball or garden party. Her designs are undoubtedly some of the most noticeable and photographed at the city’s biggest social events. Tall, elegant and statuesque, Caldwell herself is one of the best models for her designs and always graces the Best Dressed pages of the Gazette. So, what’s the secret behind her magic? I traveled to her beautiful wine country home to find out.

What I discovered: She is a genuinely happy person. Immediately, I was charmed by her vibrant personality and felt a jolt of positive energy—all of a sudden the colors in the room become brighter, the air becomes lighter and life seems easier. And I think this boost of positivity charges each and every one of her ensembles. She wants you to look like a leading lady in the film of your life.

“My style—visually it’s like a movie,” she says. “I was really influenced watching old movies with my grandparents and parents.”

She admires legendary costume designer Edith Head: “She always kept the leading lady in mind. Her designs for Grace Kelly and Tippi Hedren were just so beautifully crafted. … Whenever I have to go somewhere I try to create a character in the movie. Sometimes when you are wearing something a little bit different and eye-catching people will come up to you and say, ‘I like what you are wearing. It’s interesting. Tell me about it. Who are you?’ And it’s really nice to meet people that way. I think people are drawn to things that are classic but with that special little twist. That’s how I dress—I’d like it to be something that I would want to see in film or on-screen.”

Caldwell’s glam grandmother Carla, inspired her career. “She worked in Hollywood as a choreographer and an animation model for Walt Disney Studios in the ’30s on many projects including Fantasia and Snow White and the Seven Dwarfs. She also did background dances for some MGM films. Her stage name was Iris Nelson. She always dressed to the nines, even going to the garden to pull weeds. She’d always wear clip-on earrings, scarves around her neck, it was just that tiny extra touch. When I would go and visit her I would get shy around her, just studying her. She was so theatrical, always had a perfect posture and wore Chanel N°5. She was so ahead of her time —collected Asian antiques, travelled and did yoga. She always would have something glistening. So I think a lot of my style comes from her.”

An expert on fashion spanning the Art Deco to midcentury periods, Caldwell got bit by the design bug 30 years ago when she began “upcycling” vintage clothes and jewelry she had inherited from Carla with mixing the old with something modern.

People quickly took notice, the compliments started pouring in and upcycling turned into creating one-of-a-kind pieces that often combine contemporary textiles and skillfully executed vintage silhouettes, with details including hand-beading and hand-embroidery.

“I’ve met so many incredible women through doing this,“ she enthuses. “We end up becoming friends because we appreciate each other.”

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