There’s workwear—a chore jacket picked up from a flea market, maybe some lug sole leather boots you scored off-season—and then there’s workwear. A perennial favorite in the latter category? Overalls.

Of course, I realize that a lot of the reason that Holmes looks so cool in the overalls is due to the styling. In the photos, taken on the Happy Hours set in New York City on July 22, Holmes has ...