Everyone remembers Joseph Leyendecker's square-jawed Arrow Shirt Man. He was an American icon through the Roaring Twenties. Leyendecker's illustrations became a distinctive image representing the country's prosperous Jazz Age. However, with American economy in the midst of the Great Depression in the early 30s, manufacturer Cluett Peabody began a new ad campaign for Arrow based on value. And it's artist was James Williamson. He had become famous in the advertising world for his decade-long series of stunning ads for the Ford Model T.
For this new client, Williamson developed a light-hearted approach in his illustrations. They featured young men enjoying life in their Arrow shirts. Some of the ads take on a cartoonish quality. This proved very successful. He remained the primary artist for the brand through the early 1940s. Here's a sample of those ads.

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