Can we wear skirts while still keeping the body warm? Yes, absolutely. There are some ideas of how to wear skirt in winter that will still make you warm and fashionable as well. Scroll through to see how these street style stars winter-proof their skirts, plus our picks for getting the look. The easiest way to wear a skater skirt and stay warm is too add cozy tights, a cardigan, a sweater, and a hat.