Hanayamata, Wakaba*Girl Recommendations
Both are about a group of school girls with different personalities who become close friends. Both mc are a bit shy but they're always encouraged by their friends so that they'll dare to blossom. Both mc are a bit clueless and whimsical. Also Wakaba and Tami both have never stopped anywhere on their way home from shcool and are both from a wealthy and strict family. Their friends want to show them a good time. Sure these shows have a lot of differences too but it gave me the same type of feeling while watching.