You are going through a transition period and its a common problem. Try to work with one stylist during this transition. Book a consultation time with your stylist and discuss your final decision on the type of style you want! I suggest you start looking for photos that are similar to the style you want to achieve and share your idea with her/him.
Your stylist will then start to trim and re-style your hair gradually every 6 weeks toward that style. This way you not only grow your hair healthy, but also grow it with style.
During this transition, you can use hair accessories and different type of products as your hair grows and your stylist should be happy to give you tips on how to style it.
So stop hiding yourself and start having fun and try different styles.