In order to pull off a short or very short hairstyle, a woman has to be very confident. Long hair can be a security blanket that if removed causes terrible insecurities.
Check out these very avant gard short hairstyles and dare yourself to go get one.

Willow keeps her style classy at the Women's Sports Foundation Presents The Billies Inaugural event. This simple bob has been left soft, and styled to sweep at the neck. Long side swept bangs have been cut to add shape around the face. This style will suit square face shapes best.
How to Style:
Allow up to 2 hours styling time for hot roller setting, teasing, pinning and spraying. This long lasting style is great for all occasions.
Sharon Stone shows great confidence with this extra short choppy hairstyle. Sharon has styled her hair to be somewhat piecy and messy. This can be done by applying small amounts of wax or pomade to sections of hair using your fingertips.
Be careful not to apply too much pomade as this can make the hair appear greasy.