To mark Sarah Kerr-Dineen’s retirement as Head of Oundle School, her portrait was unveiled at Speech Day. It will join the gallery of paintings of previous Headmasters in the Cecil Lewis Room, distinguished as a portrait of the first woman to lead the School since its founding in 1556.

The commission to paint her portrait was accepted by Old Oundelian Joshua Waterhouse (Sidney 2007). Joshua said every portrait commission comes with some amount of pressure, but as an OO, the pressure felt personal. He remembers walking into the Cecil Lewis Room as a boy to sit his entrance exams, surrounded by the likenesses of the men who had previously led the School. “What an honour it is to have one of my own paintings now hanging in that room,” he said.

The setting for the portrait was the School Chapel, a place that Sarah said has deep significance for her experience at School. Seated in William Laxton’s chair in the Chapel, Sarah strikes a pose that was at first unplanned. Joshua took hundreds of reference photographs, and initially settled on a pose where she was reclining slightly at an angle, almost reminiscent of Whistler. “Then I asked her, just quickly, to try leaning forward,” he said. “I told her we probably wouldn’t use it, but she did it so naturally, folding her hands in this really lovely way.”

The resulting pose conveys a warmth and attentiveness that captured Sarah’s manner: composed and approachable. Joshua said the portrait is not as “fussy” as some of his previous portraits, with accessories and backdrops symbolising place or profession. The focus is on Sarah and, in her gaze, her relationships with pupils and colleagues who will remember time spent with her, listening intently, ready to share a laugh or make a firm decision.

Every portrait by Joshua is signed, but signifying the personal connection of the commission, he added a porcupine to his monograph in the bottom corner, in tribute to his years as a boy in Sidney House. Joining him at the unveiling was Roger Page (OO), who was both his Housemaster and his art teacher.

Joshua works on private commissions and independent projects from his studio in Somerset. He was elected a member of the Royal Society of Portrait Painters in 2024.

Above photos of Sarah’s portrait are from Joshua Waterhouse’s website.
Read about Sarah Kerr-Dineen’s ten years as Head of Oundle School here.