We have never cut Sweet Pea's hair, and it has gotten longer than shoulder length, and is pretty wild with a cowlick in the back and some curls. She doesn't like to spend much time sitting still, so we have always had a hard time getting it pulled back nicely. Luckily, our daycare provider is amazing with hair and so Sweet Pea comes home in the afternoons with such pretty creations as these: Double french braids (pay attention to the hair only, please) Pigtails with zigzag part Ponytail with headband She LOVES having her hair made pretty by her daycare provider, and I have learned a few tricks about how to get the hair smooth, how to not pull, and how to get it to stay in. I still am nowhere near as skilled as I'd like to be someday, but I have gotten better! The tips I've gotten so far are: use a spray bottle to mist the hair as you brush it out; hold the hair above the point where you are combing or removing a hairtie; and use the tight rubber bands.