After buying and selling a drawing by the same artist as this one a few weeks ago, I learned that the artist was Bill Anthony, a mid 20th century artist/illustrator from Virginia, examples of whose work (significantly more risque than this one, and also more absurd!) were presented in Josh Lowenfels booth at the 2019 Outsider Art Fair. (Blurb from artsy.net below.)  Women in short skirts and high heels were clearly his fixation, but it's the simultaneous attention paid to faces and outfits and postures and gestures and hairstyles that endears these to me, which is especially true in this one--and to my eye these two women, staring right back at us, look as though, twenty years or so later, they will be most definitely be running the boardroom! 

14 x 8 1/16". Ink on lightweight board, very good condition, with a little corner wear.

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6 Inspiring Outsider Artists You Should Know, Scott Indrisek, Jan 18, 2019:

Bill Anthony, Joshua Lowenfels Works of Art

“He’s an up-skirt guy,” joked the gallery’s Kevin Duffy, reflecting on a series of ink drawings from the 1930s by Bill Anthony. Categorized as a series of portraits of “Fetish Chicks,” the works depict various anonymous women caught in the act of retrieving money from the floor. Sure, there’s something disturbing and borderline stalkerish about such a niche fixation, but Anthony’s fine draftsmanship adds a gentle touch to what might otherwise be plain creepy. There isn’t much known about the Virginia-born artist’s personal life. Gallery owner Joshua Lowenfels posits that he worked at a television station, and identified as a “self-proclaimed illustrator” with “a certain fetish for women dropping something in a tight spot.”