From workdays to weekend plans and even last-minute errands, my schedule requires winter dresses that can do all three without any extra effort. After trying countless styles as a shopping writer, I’ve become particular about exactly what actually earns my closet space. If a style isn’t comfortable and doesn’t come with pockets, it simply won’t make the cut. This roundup includes the 17 winter picks I reach for most, including cozy sweater styles, tunic knit midis and easy wrap silhouettes. Each one is easy to throw on with boots or sneakers, layers well under coats and looks put-together with...

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