With Water For Elephants coming out, and the fact that I watch Cruel Intentions pretty much any time I find it airing on cable, I decided it might be fun to do a look back at Reese Witherspoon’s fashion through the ages. Whenever anyone asks me who I think is one of Hollywood’s best-dressed celebs, I name-check Reese, because I’ve always found she has an endless supply of really cute cocktail and day dresses that are a lot more relateable to me than red-carpet gowns. This slideshow MIGHT have me re-thinking that… but, not entirely, because she nails it more consistently than she doesn’t. However, there are certainly some doesn’t’s in here, beginning with a lot of what she wore when she was coming to fame, and then some stuff in the middle I had completely forgotten existed.

Do you think Reese has forgotten any of them? Or do you think she woke up recently and rolled over and poked Jim Toth in the back and said, “Dude, this one time? I looked like a refugee from the Singles auditions. WHAT WAS WRONG WITH ME?” At which point he was probably all, “I could get Singles II greenlit for you,” and across town someone at Us Weekly sat up straight as an arrow in bed and began casting it with Jennifer Aniston, Jessica Simpson, Jessica Biel, Renee Zellweger, and, like, Ashley Greene.