When layering in the winter months I start off with a thin t/shirt or thin long sleeve piece first, then add a dress and I often wear baggy pants under too or I'll add another loose fitting thin dress on top, as above. I like to mix textures , add a scarf or if you want to make it more casual add a denim jacket or leggings. You will probably have plenty already in your wardrobe that will match already. I also like to wear my converse boots or sneakers too. Experiment, see what you like and feel comfortable in it. You can do it.
add some denim
