There are pros and cons to wearing black- on the one hand, it’s eternally chic, on the other hand, wearing it daily invites accusations of “playing it safe.” However, what better time to test out this theory than the month of October? Thirty-one days of black wardrobe magic, unquestioned and on trend. And for playing it safe, there’s always fun accessories in orange, green or purple. To test out my theory, I compiled a nice little Pinterest look book of what I call October’s Best Dressed. I hope this inspires you to step out and step it up when it comes to the entire month of October, not just Halloween!