Clown Clothes or Cutting Edge?

WhoWhatWear Daily has started a new feature where they highlight every day women in risky, cutting-edge outfits and feature them on their email blasts. The blast they sent today made me sit up and ponder the meaning of fashion. While I hate when people are cookie-cutter and dress just like everyone else, I'm not sure if these outfits are so much "cutting-edge" as costumey, clown clothes. What is the line between being fashion-forward and being ridiculous? I am a believer that in the end, all that matters is that the clothes are pretty and aesthetically pleasing. I don't think these girls' outfits are either of those things.