Heels and Denim Shorts... Arty or Tarty?

I think every girl has fallen victim to the occasional skanky look. I've had my fair share of incidents with a bandage skirt or two.  Lately, I've been crushing on heels with denim shorts. When done right the look can be so effortlessly sexy, but I've seen it done wrong so many times. I think the best way to do it is with a loose tee plus or minus a blazer/leather jacket and thick heels/platforms. Victoria Beckham pulls it off well in the first look below. But when she pairs skin tight shorts with a tight vest, not even a Birkin can save her from looking cheap. 

It takes some balls to work the heels + tiny shorts look. My legs are definitely not ready to debut this look anytime soon, so that means more pilates for me.