This elegant combination of a charcoal suit and a black overcoat is a favored choice among the sartorially superior chaps. Black leather casual boots will add a laid-back touch to an otherwise dressy outfit. Figuring out a pulled together getup can be challenging on its own. Add below-freezing temps into the equation, and the whole thing becomes even more difficult. No worries, this here is your winter inspo. As you're progressing through your late 20s, you want to start dressing with more polish. If that's the case, getups like this are a fail-safe option.