Horror Stories: Outfits That Have Confused Your Boyfriends

So you know how sometimes you’re about to go out on a date and you’re feeling pretty damn great about your outfit selection, and then you meet up with the boy and it becomes immediately clear that the outfit you thought was artsy and cool is wildly confusing to him and he has absolutely no idea how to respond? Meh, who cares what they think, but in the interest of voyeurism, here’s what he’s thinking…

  • “Can someone, anyone, please explain to me why and girl anywhere wears those pregnancy shirts when she’s not, in fact, pregnant? You know, the ones that are fitted in the chest and then get all puffy and weird and horrible. I don’t get it.” -Leon
  • “In college, i went on an outing with a woman who wore a silky camisole number. But under it was over a complicated species of underwear that seemed to have been designed by the medieval Catholic church for the way it bound, squashed and distorted what, by rights, should have been displayed in their upright glory. I wanted to liberate what god had so lovingly crafted.” -Jim
  • “I went out to dinner with a girl who was was wearing what had recently and for whatever reason become chic: a light sweater with a droopy front collar. What’s funny about these sweaters is that often the people who buy them take themselves really seriously. So we were talking about foreign policy but I kept laughing because she looked like she was wearing a vagina and her head had sprouted from it.” -Cory
  • “I used to go out with this girl who sometimes wore a half of a shirt tied like an apron in the back. She insisted it wasn’t an apron, but I know what an apron looks like and this was it . After explaining my thoughts on the shirt I was forbidden from removing it, although it could have been done quite easily had I been allowed.” -Mike