Choosing a Casual Outfit For a laid-back vibe, pair pants with a lovely shirt. Wear jeans with a button-down shirt for men or a silky blouse or tank top for ladies for a night out. Tuck your top into your pants for a more polished look, especially if you're wearing high-waisted jeans. Get inspiration from the following celebrities: Justin Bieber, Miley Cyrus, and James Franco. For a more formal occasion, choose a suit for men or a nice dress for women. If you want to look cool, then wear a white shirt under your suit jacket or dress shirt. Finish your outfit with some stylish shoes. Take advice from the following stars: Brad Pitt, Matt Damon, and George Clooney. The choice is yours! As long as you are comfortable with what you are choosing, then that's all that matters.