Dragonfly Boudoir

Dragonfly Boudoir is an Oakland-based boudoir photography studio led by photographer Cheshire Isaacs, offering fully personalized sessions in a versatile studio near Lake Merritt. Cheshire is known for highly customized sessions built around client-provided inspiration photos, Pinterest boards, and detailed questionnaires, with in-studio looks drawn from roughly 25 distinct lighting and backdrop setups, plus options to shoot in hotels or client homes. Cheshire has been shooting professionally since 2009 and introduced boudoir to his practice in 2015, working with hundreds of clients over the years; the studio was previously known as Oaktown Boudoir. The studio is located in Oakland's Ivy Hill neighborhood near Lake Merritt, with additional shoots in the Bay Area, hotels, client homes, and occasional travel to Las Vegas. Clients consistently describe feeling at ease from first contact, credit Cheshire's posing guidance and communication style for helping them define a clear vision, and note that the final albums exceeded their expectations.