Remember that hair grows forever, it doesn't stop. If you go out on a limb, drastically change your hairstyle and end up hating it, it can always be changed to something else, another style or color. Talk to your stylist to see if they have any fun celebrity hairstyles for you. You never know, they may have a style that they have been dying to try on you, but never had the opportunity before. Most hairdressers won't try to push a new style on you (nor should they), but if you ask, they love to share their creative side.
Whether you like these women or their hair isn't as important as understanding where they are coming from. They aren't afraid to show off their fun. While these particular styles may not be right for you, we can all learn from them. Don't be afraid to ask your hairstylist to give you a do that is fun and funky. Something outside of the box. You never know when a crazy hairstyle may be just the one for you.