Why does late 2000s fashion look more outdated than early 2000s?

I tend to notice that if I watch a tv show or something set in like 2000-2004 (ish) the fashion doesn’t look that dated and many things stayed the same to now. Maybe a few pieces of outdated fashion here and there but it really doesn’t stand out.

But if I watch something set in maybe 2005 or 2006-2009, I can notice a lot of fashion that looks outdated. Like not like you landed on an alien planet, but you can tell it’s been a while since people dressed like that or had those haircuts. Anyone notice this??