Hit: Madonna, 1991
Sure beats the cone bra!
Hit: 1996, Gwyneth Paltrow
Gwynnie does minimalism right, still today, and has some nice arm candy.
Hit: Helena Bonham Carter, 1998
Compared to nowadays, Mrs. Burton sure looks spiffy.
Miss: Kate Winslet, 1998
GASP! Are those MATCHING SHOES?
Hit: Anna Paquin, 1998
Minus that sweater, a timeless look she'll be proud of for years.
Miss: Angelina Jolie, 2000
Hey Angie, Morticia Addams called. She wants her gown back.
Miss: Kate Hudson, 2001
Kate, that perm. Red. Carpet. Foul.
Miss: Winona Ryder, 2001
Where do I begin? That hair. That face. Is that actually a hole in the tulle on her dress?
Hit: Penelope Cruz, 2001
This gal knows how to wow everyone.
Miss: Bjork, 2001
Can someone else wear an animal on their dress so we can replace Bjork on the perennial worst dressed lists?
Miss: Angelina Jolie, 2001
I know she was only a presenter this year, but that's not an excuse to dress down. It's the OSCARS!
Hit: Julia Roberts, 2001
Elegant, great hair, fits well. Winner on and off the red carpet.
Miss: Faith Hill And Cameron Diaz, 2002
Double whammy bad. The shower curtain meets the Easter egg.
Hit: Reese Witherspoon, 2002
Our favorite blonde looks fresh and chic.
Hit: Catherine-Zeta Jones, 2003
I'll cut her a break for the milkmaid hairstyle since she certainly showed off that bump in a beautiful way.
Miss: Jennifer Lopez, 2003
This beauty looks radiant, but is that an extra-large doily cloth?
Hit: Renee Zellweger, 2004
Renee's pale skin is only accentuated in this bone white dress.
Miss: Diane Keaton, 2004
I know you're Diane Keaton, you can do whatever you want. But "something's gota give" on this look.
Miss: Uma Thurman, 2004
Forget Bill. Kill this "dress!"
Hit: Hilary Swank, 2005
Talk about swanky!
Hit: Beyonce and Jay-Z, 2005
This couple has it all.
Miss: Lauren Hutton, 2006
You're one of the world's first supermodels. There's just no excuse here. And is that crotch pack the fanny pack's uglier cousin?
Hit: Charlize Theron, 2006
Even that giant shoulder can't sway from naming this a hit.
Hit: Kierka Knightley, 2006
Blondes do have more fun, and Kiera is proof.
Miss: Jennifer Hudson, 2007
"And I am tellin' you I'm not goin'" to ever wear this jacket again!
Hit: Nicole Kidman, 2007
Nicole has had some amazing looks, but this one is definitely on top.
Miss: Anne Hathaway, 2007
If my memory suits me correctly, there was a matching bow on the back of this gown. Anne, you've been warned, don't do it again.
Hit: Amy Adams: 2008
Green for red-heads may be predictable, but Amy looks so beautiful here, I don't even mind.
Hit: Heidi Klum, 2008
Here's a supermodel who knows how to dress. No blending in with this red carpet.
Miss: Naomi Watts, 2009
This looks like it belongs as the cover of the movie, "Splash."
Hit: Sarah Jessica Parker, 2009
That's Princess SJP, to you.
Miss: Charlize Theron, 2010
Hit: Demi Moore, 2010
Demi looks half her age here and twice as elegant on a 1-10 scale.
Hit: Diane Kruger, 2010
This dress is so perfect, I'll cut Diane a break for blending in with it.
Hit: Natalie Portman, 2011
Natalie was glowing and not only because of her big win.
Hit: Jennifer Lawrence, 2011
This red carpet rookie's simple look put her on everyone's style radar.
Miss: Florence Welch, 2011
It wasn't as bad as her green goblin dress at the 2013 Grammys, but, well, this isn't good.
Miss: Angelina Jolie, 2012
She looked fine, but no one likes a girl trying too hard to get attention.
Hit: Meryl Streep, 2012
Age-appropriate, yet still oozing sex appeal.
Miss: Glenn Close, 2012
I know she's 65-years-old, but take a note from Meryl Streep (see above). This is matronly.
Hit: Jessica Chastain, 2012
No "help" needed here!
Hit: Gwyneth Paltrow, 2012
Last but not least...This is my favorite look of all time. Glamorous, elegant, simple, timeless. Just as a starlet should for the Oscars.