In the summer, picking out a new dress is simple: You grab the most lightweight one you can find, and then you put it on. But when the temps go down and the number of layers required to even think about opening your front door go up, picking out a dress can become, well, tricky. You have to choose one that’ll look good with a pair of tights (or fishnets, if you dare), or something knit that’ll lay nicely over a pair of jeans. Or, if you’re looking for something that can double as both workwear and party-appropriate, you’ll have to do some serious hunting.
But restocking your wardrobe doesn’t have to be stressful. We found 25 cute winter dresses—including a mock-neck knit iteration, a work-ready floral crepe dress, and a red velvet number that’s perfect for every event from now till March—to add to your closet now. Oh, and if you’re really not sure how to wear them in the winter, check out these styling tricks that’ll double your cold-weather wardrobe STAT.