While thinking about crop tops may conjure up images of tiny tanks and low-rise jeans, Oprah put her own spin on the trend by layering a cropped turtleneck sweater over a white button-down shirt.

In that film, the funnyman, now aged 76, plays a political consultant who famously rocks a chunky white fisherman knit sweater. The iconic item is now the hottest cold-weather garment, with ...