November 15, 2013 Street Style What To Wear To Get A Second Date: 10 Hot Outfit Ideas You have a date. Step 1: Congratulate yourself on your active romantic life. Step 2: Panic about what to wear. If this process sounds familiar, we sympathize and are here to help. While date night dressing may seem complicated, we believe we’ve got it down to somewhat of a science. It’s all about striking the right balance.