 Around 1897, Oakley and her sister Hester rented a studio space at 1523 Chestnut Street, Philadelphia in the Love Building.The sisters decorated the space with furniture loaned by their mother and a combination of antiques, fabric, and copies of Old Master paintings.Oakley and her friends, the artists Elizabeth Shippen Green and Jessie Willcox Smith, all former students of Pyle, were named the Red Rose Girls by him.