The Fun Shirt

Brooks Brothers' legendary "fun shirt" traces its roots back to the 1970s. Then Brooks Brothers VP Ash Wall (fifth-generation descendant of founder Henry Sands Brooks), spotted a pile of shirts during a factory visit. Each one was made from a cornucopia of fabric scraps—no less than 10 different colors, and all of them striped—by employees who were just learning how to sew. As the company explains it, Wall said of the garments, "Those are some fun shirts," and the name stuck. While traditionally made out of oxford cloth, this poplin version from the brand's slimmer-fitting, youth-oriented Red Fleece line is made from a summer-friendly pinpoint fabric, ideal for Memorial Day weekend weather. Hidden straps at the sleeves allow you to roll it up with ease, and double chest pockets give it an even more casual feel—not that you'd be wearing this to work. It's a re-imagined prep staple that wouldn't look out of place all along the Eastern Seaboard and beyond. And at half-off, maybe you can afford to splurge on some beach-front housing for the weekend.

$79.50 / $39.75, at Brooks Brothers