Using images from more sexist eras in modern ads can be tricky business. If people trust your motives, it can be sassy and ironic. But if your motives are questionable, it can just make you look out-of-touch.
I will guess that the ad above, created for the Canadian Wheat Board, was intended to be sassy and ironic. But it was not taken that way. According to Adfreak's David Kiefaber, "The ad has drawn criticism from the National Farmer's Union for using what critics say is an irrelevant and sexist image to hype the Wheat Board's services."
The CBC has more:
"What an image of a long-legged woman straddling a fence has to do with selling grain is beyond me," Joan Brady, NFU women’s president said in a news release.
Brady said the CWB apparently doesn't realize that women are farmers and make decisions about who they want to do business with.
"Whether in our own right or in partnership, we are deeply involved in all aspects of farming," she said.
I think the problem here is that the Wheat Board is in an industry that is perceived as conservative and old-school. So even if they approved the image as a way to seem more hip, because of the context they were taken at face value. You could advertise a bar or a rock concert with this. But perhaps it's too soon for a big agriculture to be postmodern.
The image is a 1969 Gil Elvgren pin-up titled "Hi-Ho, Silver".