You can enjoy the comfort of wearing an oversized dress without anything tying it close to your body or opt for a belt to give it some shape. Leggings or tights underneath will provide extra warmth and coverage. If you go that route, you can go extra-casual with a pair of sneakers (try Converse) or dress it up a bit with boots. If it's too warm for leggings and boots, slip your feet into a pair of casual flat sandals and enjoy one of the most relaxed outfits you've ever experienced. One more option: Treat the oversized dress like a shirt and wear it with jeans (especially if your dress is a button-up style).