Channel your inner British gentleman and try pairing a white and blue dress shirt with tobacco gingham dress pants. Double monks are a goofproof footwear style here that's full of character. During the winter season, when functionality is critical, it can be easy to surrender to a less-than-stylish outfit in the name of practicality. This outfit, however, is a practical illustration that you can actually stay comfy and remain equally stylish in the winter season. This ensemble proves that in your late 20s your outfit options are looking great.