The term ‘hobble skirt’ came into popular use in the early 1910s, when a European fashion trend started by French designer Paul Poiret introduced long skirts that were narrow at the hem, thus ‘hobbling’ the wearer. Some attribute one of Poiret’s inspiration to Mrs. Hart Berg, the first American woman to join the Wright Brothers in air. To keep her skirts from flying out of control while airborne, she tied a rope around them below the knees (Katherine Wright, sister of the flight innovators the Wright brothers, also did the same shortly afterwards).
For a short while, the tighter the skirt, the more fashionable it was. This also brought about accessories such as the hobble garter (you can see one in tbe PBS series The Manor House) designed to limit the wearer’s stride so that she would not cause the skirt to rip. This trend died shortly afterwards due to the impracticality of such a garment, particularly with the introduction of cars (the skirts making getting in and out of one a bit of an adventure).
Bill Cunningham casually mentioned the hobble skirt in a recent On the Street feature about pencil skirts.