This article examines descriptions of women and airplanes in the pages of American and French interwar fashion magazines. Samples from Femina, La Gazette du Bon Ton, Harper’s Bazaar, Ladies Home Journal, Vogue (American and Paris editions), and Women’s Wear Daily illustrate how the relationship between women and transportation technology evolved to promote messages of female independence, illustrated by aviatrix ensembles from Madeleine Vionnet and Elsa Schiaparelli. These designs and representations of them in transatlantic media fused the body with the machine, presenting what Jessica Burstein describes as “cold modernism.” But these same publications also played on an imperialist sense of superiority, trafficking in racial slurs and cultural bigotry, a preponderant phenomenon described by Anne McClintock in her book Imperial Leather. Ultimately, the spectacularization of aviation and style in fashion media exposed borders that represented either freedom or confinement for women: borders between the nimble body and the clothing that restricted it, between sedentary flesh and flying machine, between the stationary present and the fast-moving future, between the familiar “I” and the unknown other. This article uncovers those technological thresholds and the fashionable women who dared to cross them.