Consider pairing a white and red and navy dress shirt with blue jeans to put together an incredibly stylish and modern-looking laid-back ensemble. Ankle boots are a safe footwear style that's full of character. During the colder months, when practicality is critical, it can be easy to settle for a less-than-stylish outfit in the name of functionality. But this outfit is a clear example that you can actually stay comfortable and remain incredibly chic at the same time in the colder months.