For a casually classy look, go for a blue blazer and a white and navy vertical striped dress shirt — these two items play beautifully together. And if you wish to effortlessly dress down this look with a pair of shoes, add tan suede desert boots to the equation. As this getup is a clear example winter doesn't have to mean dressing like a marshmallow. Those who wonder how to rock edgy casual dressing as you move through your 20s, you have your answer.