For an off-duty ensemble, consider pairing a black shearling jacket with black leather skinny jeans — these pieces work beautifully together. Take an otherwise standard ensemble down a classier path by slipping into a pair of black leather ankle boots. During the colder months, when comfort is key, it can be easy to settle for a less-than-stylish look in the name of functionality. But this look is a striking illustration that you can actually stay comfortable and remain equally stylish in the colder months.