How to not feel shy while wearing your hair down?

I've never worn my hair down before i always tuck it up in a ponytail or when i really really want to feel glamourous i wear it half up half down. I just cant go out with it all down especially in school because i feel like im going to get a lot of attention since it is very long. I want to cut a few inches off of it and challenge myself to wear it down and finally feel good about myself. But can you guys help me? Idk maybe ill feel shy again and tuck it again in a ponytail?