Tool Academy contestant in heels?

I wouldn't say that I am a fashion trendsetter by any means... I'd consider myself to be more of a fashion risk-taker in my group of friends, but I am usually not on the cutting edge in the grand scheme of the rest of the world. However, there is this new style I've been wanting to try out and I'm a little nervous about it. It's one of those trends that looks cute on some people, but I'm afraid I'll be the one that looks like a tool (see far right picture below—Exhibit A—Heidi Montag). Ladies and gentlemen, I give you socks and heels:

socks+heels

I saw some cute/cheap mary janes on sale at Target the other day that made me think of the third picture...and of course, since Target wants to reinvest every penny that I make back into their store, they also just so happened to stock cute socks. I think I'm going to give it a go this week...I'll let you know how it goes.