I absolutely love the film Clueless as it represents all that I can remember about the 90s in addition to the Spice Girls. The costumes are so great, especially Cher's preppy style which was picked out by her computer. Checked skirt and matching jackets were a yes yes, complimented with a sleeveless jumper vest over a pressed shirt. The costume designer for the film, Mona May, actually constructed the style for the film based on her imagined reality of 90s high school life. She wanted to create a look that contrasted to the more grungy trend prevalent at the time. However the film became a style piece in itself and spurred many copycat trends.
Above is my interpretation of Cher's look in the tennis scene in the movie. I always thought it was so great that they all dressed in such inappropriate clothes for sport.
T-shirt - Jigsaw, Spaghetti Strap Dress - Topshop Slip, Cycling Shorts - AA,
Fishnets - Muji, Trainers - Converse