I used to wonder about that myself, and this was an issue I had with "Sabrina the Teenage Witch" as well; why nobody on the show wore actual fashions teenagers of that time really wore.
I was in high school during the early 2000s in the Midwest and the South, and believe me, nobody dressed like the characters on "Lizzie McGuire" or "Sabrina the Teenage Witch." Most of us wore T-shirts and bell-bottom jeans (the Millennium versions weren't as extreme as the actual 1970s bell-bottoms). The sluttier girls wore "belly shirts" with hip-hugger jeans that just barely clung to their hips.
Meanwhile, I see Lizzie and her friends wearing stuff, as you said, that was ridiculous, gaudy, and downright outrageous. It seemed the only time they came even close to wearing real jeans was with studs and bright embroidery all over them! And forget about ordinary shirts. They always wore stuff like studded jeans vests, brightly colored layers of tops, things like that. Sabrina was even worse. She'd run around in haute couture dresses or stuff young, 20-something interns in offices would wear to impress the boss. Either that, or they were outfits no teen could afford.
I do have several explanations behind that, but the biggest one is, the costume designers for these shows live in L.A, and don't have a CLUE what real teenagers actually wear to high school, unless it's a local one in the L.A. area. My aunt lives near there, and she says they wear all sorts of expensive, up-to-date looks (just to show how spoiled and rich they are), which is not in any way representative of how real teenagers in most parts of the US dress, even today.
The second explanation is, Lizzie and her friends (and coincidentally, the Stevens siblings) all live in Sacramento, so it's possibly understandable about their choice of crazy, colorful, outrageous clothing. Now if there are any natives of that city that can confirm this, I won't argue. But I get the feeling most teens in Sacramento don't wear gaudy, outrageous fashions to their schools either.
The third explanation is, this is all done on purpose. It's rare to see anybody wear ordinary, everyday fashions that real people out in America wear. The people who make these shows assume that just because the students live lives that are interesting, they should wear interesting stuff too. So they deliberately have them dress in up-to-date fashions that no ordinary teen could afford, much less want to wear to school for fear of being laughed at.
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