drugstore cowboy noun2 •(old-fashioned) Someone who dresses and acts like a cowboy but has none of the skills.When we first came to California and we started putting on Westerns, there were no riders in Hollywood; they were all drugstore cowboys. — 1974 •A young man who loafs around town, especially a lady's man who hangs out in public places in an attempt to pick up girls.When any of these jazz-age drugstore cowboys starts trying to fool around with his sister, he won't mince his words. He'll say, "See here, now, what do you mean, trying to ruin my sister?" — 1934 formsdrugstore cowboys