The story of the work shirt begins in 1900 with Sears, which was then called Sears Roebuck & Co. The store sold a number of durable top layers called Working Shirts, a staple of the workwear category.

Long-sleeve button-down denim shirts are the standard. They layer, you can roll up the sleeves and they transition well from casual to workwear. But if you’re after that preppy look, a good ...