Essay: Finding Confidence in an Old-Fashioned Portrait Session

A best self is revealed by sitting for a portrait.

In this day of selfies, there are few opportunities to have your portrait painted and even fewer reasons to do so. As the owner of a contemporary art gallery called Portrait Society, I do occasionally encounter a painter who does portraits. One such artist, Lon Michels, with whom the gallery had recently started to work, asked me to sit for him in part so I would understand more about his process.

I responded, “Oh yeah, sure,” fully intending to back out. Lon, however, would not let me slip out of the agreement. So eventually I went to the home he shares with his partner and artistic collaborator, Todd Olson, to sit for a portrait.

Upon arrival, Lon and Todd insisted on applying lots of makeup and false eyelashes to my unadorned face. They gave me their version of the star treatment, hovering over me like giant hummingbirds, trying their best to glue down the lashes with their big man hands. I was at their mercy and slowly relinquished control in exchange for a glass of champagne.

Wearing a simple black dress and my favorite vintage Parisian red leather go-go boots, I sat on a chair in Lon’s studio, about 5 feet from him. Lon knew I was nervous, and to help put me at ease, he wore something outrageous: a Batman onesie costume. He claimed he found it at a resale store, but I suspect he had it custom-made to fit his 6-foot-6-inch frame.

Whether it was the onesie or, more likely, Lon’s generous and charming nature, I was not bothered by the act of being “looked at.” In fact, it was much more pleasant than being photographed, because you don’t have to freeze a smile while waiting uncomfortably for the shutter to click. 

What struck me the most about sitting for a portrait was that it isn’t a prescriptive experience. Neither the artist nor his subject know where it is headed. We both had faith in the process, and that’s about all. It felt like a heightened kind of human sharing, a way for two people to be together outside the conventions of chatter. Sitting for the portrait felt both like a celebratory event (eyelashes, champagne and Todd chittering about) and also like a quiet and intimate exchange.

Two hours passed effortlessly, and I was surprised when Lon said he had completed the initial painted sketch. Lon always makes his subjects look great, so I knew he would cinch the waist, enhance the curves, enlarge the eyes. But I was a little concerned that this might actually prompt feelings of insecurity as I noted the distance between rendition and reality.

I am happily surprised to report that it did not. Lon’s portrait of me is decidedly glamorous, consistent with his style. But even though it looks more like an Italian movie star from the 1960s, there is something of me in it, or at least something I’d like to claim. He rendered me front and center in the art gallery with my dog, Spruce, by my side. I’m staring directly out of the picture in a determined way, almost as if my painted image is challenging the real me, telling me to face forward and believe in myself. When I look at it, I’m inspired – not to exercise more or look better, but to unflinchingly sit in the world with confidence.

I really like my portrait, and I like the idea that when I’m dead, one of my kids might have it on their wall, and they will remember my beauty and vitality, hopefully more than the decline they will inevitably witness. Long live the portrait!

‘Me, on Canvas’ appears in the May 2018 issue of Milwaukee Magazine.

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Debra Brehmer, an arts writer and curator, owns and operates Portrait Society Gallery, a contemporary art space in Milwaukee. She was also the former editor and publisher of Art Muscle Magazine and teaches part-time at the Milwaukee Institute of Art and Design.