Criss learned the art of dressmaking from her mother and later passed on her skills by offering a program in the Richmond area for young women to develop their sewing skills.[1][3] She started as a seamstress who traveled home to home, as many did.[5] Criss became the city's most celebrated designer in the early 1900s, charging up to $200 for her elegant, handmade dresses.[1][3][6]
With the help of her housekeeper and two or three young women, Criss designed dresses for the white elite in Richmond.[1][7] Criss was well respected by her patrons and was well known for her beautifully designed wedding gowns.[1] Criss's elite client list was made up of New York's most respected families.[8] The second day dress, designed by Criss in 1896 and worn in the Richmond high society wedding of Miss Ellen Clark to Mr. Gordon Wallace, was donated to the Valentine Museum in Richmond, which has the second largest collection of period costumes in the United States.[1][7]
During Criss' rise in notoriety, she adopted the professional title 'modiste,' which established and solidified her as an African American creative professional, during a time in which legislation provided barriers for progressing Black businesses. [8]
A wool two-part dress of Criss's was featured at the "Pretty Powerful: Fashion and Virginia Women" exhibit in Richmond, Virginia, from May 2018 until January 2019.[5]
Maggie L. Walker, the first Black woman bank founder and president of St. Luke's Penny Thrift Saving Bank, was a neighbor on West Leigh Street in Richmond and became one of Criss's many wealthy clients.[1][3] Outside of a professional client relationship, Walker openly and actively supported Criss' work and openly critiqued the lack of communal support among Black entrepreneurs at the time. [2]
Gloria Swanson, who was once the highest paid actress in Hollywood, was one of her more prominent clients.[1][3]
Criss was neighbors with Sara Breedlove Walker, better known as Madam C. J. Walker, with whom she also enjoyed a close friendship.[1][3] Criss also designed dresses for Walker's daughter A'Lelia Bundles.[1][3]