The idea of “who wore it better,” so popular in supermarket magazines, is apparently nothing new. Jessie Gillespie, an illustrator for the New York Tribune and the Washington DC Evening Star, published witty observations of current styles. Above are her takes on the trend of tight long skirts and inventive hats in 1914.
What I love about Gillespie’s illustrations is that she shows current fashion on a variety of age groups and body types. In some of her “Silhouette Studies” there are even a few African American faces, rare in a newspaper aimed at a white audience.
You get the sense that Jessie Gillespie used her drawings somewhat like a street photographer, capturing the wide range of clothing, hats, and hair styles that she saw on any given day.
Gillespie was a prolific illustrator, doing fashion drawings and commercials for many magazines, including the original Life, Ladies Home Journal, and Vogue. But I like her best when she turned her keen eye to the comedy of clothes. Read more about her here.