1. 1998: EMMYS
Oh, my. The hair, the bag, that dude standing behind her (OK, that's not her fault). Here, Katie Holmes and her Dawson's Creek co-star, James Van der Beek, attend the Emmy Awards and/or senior prom.
Grade: A. (For Effort and '90s nostalgia)
2. 1999: GO Premiere
Really? In 1999, we would have pretty much died to go to a movie premiere. We would have begged our mom to buy us a new dress at Wet Seal and bragged to all of our friends. We wouldn't have worn this.
Grade: D. (Pharmaceutical account coordinator's first day in the workforce.)
3. 2002: TRL!
Katie seems to be saying, "Is this OK? This is OK, right? I thought so." Yes, this is OK, but just OK. We remember that denim wash, Holmes. You're right on trend, but we take issue with that pant length.
Grade: B. (Not terrible, but do your hair. You're on TRL!)
4. 2003: WB (RIP) Upfronts
Oh, dear. Katie went from tough chick to Easter chick with this horrifying dress. Worse, she totally doesn't mesh with her castmates (from L-R, James Van der Beek, Kerr Smith, Michelle Williams and Joshua Jackson).
Grade: F. (What were you thinking?!)
5. 2003: Pieces of April NYC Premiere
This is a little more adult, right? Much better. Also, she looked adorable with Chris Klein (we know, that's not the point).
Grade: B. (A step in the right direction.)
6. 2005: Fall Fashion Week, NYC
Here's Katie (with Claire Danes!) at what's probably her first fashion week experience. She wore this lovely satin sheet to the Calvin Klein show. Joey Potter got a great fashion orientation this year — she also went to the Vera Wang show and hung out with Carolina Herrera at the Fragrance Foundation's FiFi Awards.
Grade: C. (Shapeless sheet, but excellent color choice.)
7. 2005: MTV Movie Awards
There's no denying that when Katie started dating Tom Cruise, she started making smarter style choices (still, we attribute this more to her maturing and not, you know, Tom's influence). We dig the hair and the plunging neckline of the jumpsuit.
Grade: B+. (Fab outfit, not sure about the accessory.)
8. 2006: Mission Impossible III
Hmm. This appears to be a velvet sack with poorly sewn bow on it.
Grade: F. (Fit for a child at a family Christmas party. But not Suri, she's far too fabulous.)
9. 2006: In Paris With Posh
BAM! Can you believe this was the same year as the previous picture? This looks like an ad for something sexy. We love everything about this: the black tights, the high waist, the insane flare, the big sunglasses, the hair whipping in the wind. Good for Katie for pumping up the volume when in Paris with Victoria Beckham!
Grade A: (When in Paris with Posh...)
10. 2007: Hairspray Premiere
BAM! AGAIN! Katie finally shows us some bare thigh and strikes a pose at the Hairspray premiere.
Grade: A-. (Sorry, we like you better with long hair.)
11. 2009: Dizzy Feet Foundation Fundraiser
Katie skipped the Dizzy Feet event in 2012 — it was supposed to be her first red carpet appearance since splitting from Tom Cruise. We don't know what she would have worn, but we loved her look in 2009!
Grade: A. (Sleek and fabulous.)
12. 2011: Solo at the Emmys
A sign of things to come (in terms of Katie's solo appearance, we're not reading into her color choice)? Katie presented at the Emmys in 2011, and took everyone's breath away while doing so.
Grade: A. (Relaxed and happy!)
13. 2012: David Letterman appearance
We're in love with this outfit!
Grade: A. (We love those red pants almost as much as we love you.)