Gokinjo Monogatari (Neighborhood Story) came out in 1995. It follows the lives of a group of fashion students. A number of styles are represented, but I wanted to share some screencaps of one particular character, P-chan, who donned some adorable 90s Lolita outfits!
In the show, she is portrayed as loving dolls and childish things, constantly carrying around her teddy bear named Pucci Francois. She's a sweet, loveable girl and kind friend to the others. Her outfits often feature some kind of hat and frequently involves plaid in various colors. I like how cutesy-carefree she is and how poofy her pigtails are under her large-brimmed hats and headbows <3