Mezue nkebi ahịrịokwu a: Mgbe di mbụ ya, bụ́ Thomas Henry Watkins, nwụchara, Preston malitere ịrụ ọrụ dị ka onye na-ese ihe osise iji na-egbo mkpa ya. Ọ na-akpakọrịta ma na-egosipụta ndị na-ese ihe nke ụlọ akwụkwọ Ashcan ma lụọ otu n'ime ndị otu ahụ, James Moore Preston, na 1903. Ha gara Europe ọnụ, nọrọ n'oge okpomọkụ na Long Island, ma soro kọwaa akụkọ magazin. Ọ ghọrọ onye na-ese ihe na-aga nke ọma maka magazin, dị ka "Harper's Bazaar" na "The Saturday Evening Post", ma bụrụkwa onye na-ese akwụkwọ na-aga nke ọma. A na-ewere ya dị ka otu n'ime ndị inyom kachasị elu n'etiti 1900 na 1940, Preston bụ otu n'ime ụmụ nwanyị ole na ole na ndị na-egosi ihe ngosi nke Society of Illustrators, ebe a nabatara ya na Machị 29, 1904 mgbe ndị ibe ya Florence Scovel Shinn, Elizabeth Shippen Green, Violet Oakley, na Jessie Willcox Smith. Dịka ha, ọ bụ naanị onye otu Associate ebe ọ bụ na anaghị anabata ụmụ nwanyị ịbụ ndị otu zuru oke ruo afọ 1920. O gosipụtara na Armory Show nke 1913 ma merie ihe nrite na
Panama <unk> Pacific Exposition na 1915. Preston bụ otu n'ime ndị isi na-ese ihe nkiri. Ọrụ ya dị n'ọtụtụ ebe ngosi ihe mgbe ochie. O mere onwe ya otu isiakwụkwọ nke usoro ihe nkiri "Our Mutual Girl" nke e gosipụtara n'ụlọ ihe nkiri na 1915.