If you're hunting for a casual but also seriously stylish look, try teaming a red and navy dress shirt with a skater skirt. Add a dose of sultry class to this outfit by rocking black leather ankle boots. In winter, when warmth is prized, it can be easy to surrender to a less-than-stylish getup. This getup, however, is a good illustration that you totally can stay snug and remain equally stylish during winter.