Consider wearing a charcoal overcoat and charcoal dress pants - this look is bound to make an entrance. For something more on the daring side to round off your getup, add chelsea boots to this look. Piecing together a pulled together combo can be a bit of a juggling act on its own. Add subzero temps into the equation, and the whole thing becomes even more difficult. No worries, this here is your winter outfit inspiration. So if you're looking for style tips on how to dress in your late 20s, this combo is a perfect example.