In the 20s and 30s there were several features that tried to combine the comic strip (or in this case, panel cartoon) form with fashion advice. None did very well, and Style Smiles is the least successful of the ones I’ve been able to track down. It was an offering of Esquire Features and started running sometime in 1937. The fashion illustrator/cartoonist on the feature was Gretchen Philips. She dropped out in 1939 and the feature was taken over by someone named Dotti*. I’m afraid I know nothing about either of the creators. The feature ended sometime in the early 40’s, probably 1942 or ’43.
*EDIT 12/7/17: Dotti’s daughter has contacted me and tells me her mother’s name is Dorothy Smythe Swanson.