Bill Cunningham Costume Bill Cunningham

Thinking of the perfect Halloween costume, while still keeping things easy and fuss-free, can be a seemingly impossible task. Instead of racking your brain trying to come up with an idea that will ultimately fall flat, follow our shopping guide to make sure you stand out this year. We've rounded up five of our favorite fashion industry insiders to dress up as this Halloween. From an infamous photographer to the model of the moment, click through to find out how to get their looks using 4 items or less.