For a laid-back and cool ensemble, dress in a v-neck t-shirt and charcoal jeans — these pieces go wonderfully together. Black leather ankle boots will instantly lift up even your most comfortable clothes. In the colder months, when practicality is top priority, it can be easy to settle for a less-than-stylish ensemble. This ensemble, however, is a bright example that you can actually stay toasty and remain equally incredibly stylish in the colder months.