This casual combo of a light blue denim jacket and black jeans is ideal if you need to feel confident in your look. Stick to a more elegant route on the shoe front by wearing a pair of burgundy leather casual boots. During the colder months, when comfort is the priority, it can be easy to settle for a less-than-stylish look in the name of functionality. However, this look is a vivid example that you can actually stay cozy and remain stylish at the same time in the colder months. Wondering how to dress as you make it through your 20s? This pairing is the perfect answer.