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Painter, teacher, art teacher and silk painter was born in Perth, Western Australia on 12 October 1845 to Walkinshaw Cowan and his wife Elizabeth n_e Dyer. Cowan had arrived in 1839 aboard the Brothers, his wife eight years earlier on the Drummore. At the time of Jessie’s birth Cowan was 'Clerk to Council’ a position he achieved the year of his arrival. In 1846 he became Secretary of the Government Grammar School but by 1848 was the Protector of the Aborigines 'Over the Hills’ in the rural district of York, Western Australia where he became Resident Magistrate from 1873-88. The family home is now the Residency Museum in York. It is not known how Jessie was educated. Many of the daughters of the gentry learnt from their parents or governesses, the other classes at the convents run by Irish nuns or at the “chapel” schools. Given their later skills it is possible the Cowans were sent to Perth to the Young Ladies Academy, which offered “Every facility afforded to young ladies for the acquirement of a thorough English Education”. This was run by the Sisters of Mercy who advertised that they taught French, Italian, music, drawing, painting in watercolours and illuminating.
Eldest sister Agnes and Mrs Knight opened a boarding school in Perth in the late 1860s. In 1868 when Mrs Knight retired Jessie and sisters Annie and Lily went to help at the school. Jessie taught drawing. A pupil, Edith Dircksey Brown, married their brother James in 1879 before becoming a noted feminist and the first woman parliamentarian in Australia. Edith’s elder sister Blanche was also a pupil at the boarding school. Jessie assisted at the school until her own marriage in 1874 to Joseph Hillman, brother of the diarist. They had three children Alfred born 1875, Jessie 1881 and Lillian 1883. A stillborn child was delivered in 1879 and she nearly died having Jessie. Hillman who had been a clerk in the Western Australia Bank before they married became a clerk at the Treasury and Public Works in 1874. In 1881 he was Government Clerk in the newly opened Railway Department. Hillman was also treasurer of the Turf Club from 1874 and member of the Weld Club committee. In the Hillman diaries Jessie is recorded as dressing as “[c]omin thro’ the Rye” to the Rinking Club’s fancy dress ball held in the Perth Town Hall 17th October, 1878. Roller skating was apparently a favoured pastime. A rink was even set up by Lady Robinson in the Government House grounds where the ballroom is now.
In August 1881 the Hillmans moved from Perth to live in North Fremantle with Agnes who had opened another school, which ran from 1876 to 1887. This was a large three-storey building which had been a hotel. In 1881 they attended the International Exhibition arranged by Joubert and Twopeny in Perth in their “[i]ron palace on the green”. Not long after this she painted the lilies on her ex-pupil Blanche Habgood’s dress. She died in 1893.
Blanche Mary Elizabeth Brown (b.1860) was a pupil at the boarding school. Blanche was the daughter of Kenneth Brown, pastoralist, a partner with his brother Maitland at “Glengarry”, Champion Bay and his first wife Mary Eliza Dircksey Wittenoom, teacher and daughter of the colonial chaplain the Rev. J. B. Wittenoom. In 1880 Blanche married Robert Henry Habgood, son of Robert Mace Habgood jeweller and merchant of Perth and London, Liveryman of the Worshipful Company of Goldsmiths.
Jessie is noted for the lilies painted on Blanche’s wedding dress. The two-piece dress of heavy cream ribbed silk and silk taffeta was made from the same fabric that her sister Edith had used the previous year for her wedding dress. About two years after her wedding Blanche’s dress was 'renovated’ to become an evening gown. At this time the sleeves were removed and the tiger lilies were painted onto the taffeta panels. Edith Cowan later surmised it might have been dyed in coffee to change its colour before being painted by Jessie Hillman “who painted beautifully”. Today it has a plain tight bodice with pointed waist, deep V d_colletage and the small puffed shoulder straps so fashionable about 1882. The bodice is trimmed at the waist with grosgrain ribbon. The silk taffeta panels are painted with pink and white tiger lilies with green leaves and stems. Helena, wife of Blanche’s son Robert wore the dress to a Western Australian Centenary ball in 1929. The dress has been stabilised and restored with a gift from the Utah foundation. It is permanently on display at Stirling House, the headquarters of the Royal Western Australian Historical Society.