Consider wearing a navy and green blazer and a white and blue vertical striped dress shirt if you're going for a proper, seriously stylish ensemble. To add a mellow vibe to your look, introduce a pair of brown suede casual boots to your outfit. During the colder months, when comfort is above all, it can be easy to settle for a less-than-stylish outfit. But this outfit is a striking example that you can actually stay cozy and remain stylish during the colder months. Surely a great choice if we're talking dressing ideas for over-30 guys.