6 Winter Dresses for Every Cold Weather Occasion Vogue Discover 15 Winter dresses with boots and big sweater with tights ideas black dress and tights with brown boots, fall dresses sweaters & cardigans, gucci soho crossbody bag and more pairing a cozy sweater dress with black boots is a classic combo for winter fashion. , when selecting a sweater dress, make sure it's flattering and not frumpy. a belt can cinch in the waist just Winter Boots You Can Actually Wear With a Dress WSJ