December 18, 2013 Experts 11 Things You Should Never Wear On A Date--Are You Guilty? When it comes to dating, there are plenty of things to worry about (Who pays for dinner? How to word that text?), but your outfit shouldn’t be one of them. As such, we tapped style bloggers like Danielle Bernstein of We Wore What and Natalie Suarez of Natalie Off Duty to weigh in on fashion red flags.