This project is a short history of the life of Jane E. Westover and the world in which she lived. Known only by her obituaries which traveled in newspapers the world over, Jane Westover lived her life dressed in "men's clothing" and acted as a barber for the majority of people in central Connecticut. The Gentle Expert recovers and reconstructs the hardships of Westover's life and death. Westover was pathologized by neighbors, suffered extreme bodily pain, and ultimately had her property seized by a local family in power. Still, Westover's life was marked by authenticity and joy; she lived with two women at separate times for the majority of her life until death, enjoyed a lucrative business, and was memorialized in newspapers alongside some of the most famous gender-benders in history.  

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Drawing on recent histories of trans and gender non-conforming people, The Gentle Expert  assembles Westover's life as part of this incredible archive. From census data and church records to last wills and testaments, I uncover Westover's complicated life as a "woman in men's clothes" in a quiet New England town. Though we cannot definitely know if Westover "was trans," this study contributes to trans history by offering an account of a nineteenth-century life lived by an incredible self-starter in a derby hat.