WEST HOLLYWOOD, CA - AUGUST 20: Actress Ashlee Simpson-Wentz and actress Katie Cassidy arrive at InStyle Magazine's 8th annual Summer Soiree held at the London Hotel on August 20, 2009 in West Hollywood, California. (Photo by Alberto E. Rodriguez/Getty Images)
This was when they were both in the rebooted Melrose Place, and I actually remember both of these looks. I still don't know what Ashlee is thinking, although I think this could be saved with different styling. Honestly, Katie looks great.
Mindy Kaling
WEST HOLLYWOOD, CA - AUGUST 20: Actress Mindy Kaling arrives at InStyle Magazine's 8th annual Summer Soiree held at the London Hotel on August 20, 2009 in West Hollywood, California. (Photo by Alberto E. Rodriguez/Getty Images)
Does Mindy need some jewelry with this?
Jessica Chastain
WEST HOLLYWOOD, CA - AUGUST 20: Actress Jessica Chastain arrives at InStyle Magazine's 8th annual Summer Soiree held at the London Hotel on August 20, 2009 in West Hollywood, California. (Photo by Alberto E. Rodriguez/Getty Images)
Well, well, well, look who it is! A pre-fame Jessica Chastain. (She'd done some stuff but nothing that flashy; The Help was in 2011). This is good?
Eliza Dushku
WEST HOLLYWOOD, CA - AUGUST 20: Actress Eliza Dushku arrives at InStyle Magazine's 8th annual Summer Soiree held at the London Hotel on August 20, 2009 in West Hollywood, California. (Photo by Alberto E. Rodriguez/Getty Images)
NOTHING says 2009 like a bandage dress and a pair of RockStuds! (I do love this clutch.)
Taye Diggs and Idina Menzel
WEST HOLLYWOOD, CA - AUGUST 20: Actor Taye Diggs and singer Idina Menzel arrive at InStyle Magazine's 8th annual Summer Soiree held at the London Hotel on August 20, 2009 in West Hollywood, California. (Photo by Alberto E. Rodriguez/Getty Images)
Idina is wearing a nightgown because it's AUGUST and she is literally two weeks away from having a baby! WEAR WHATEVER YOU WANT, LADY.
Dania Ramirez
WEST HOLLYWOOD, CA - AUGUST 20: Actress Dania Ramirez arrives at InStyle Magazine's 8th annual Summer Soiree held at the London Hotel on August 20, 2009 in West Hollywood, California. (Photo by Alberto E. Rodriguez/Getty Images)
This is successful and has aged quite well.
Maggie Grace
WEST HOLLYWOOD, CA - AUGUST 20: Actress Maggie Grace arrives at InStyle Magazine's 8th annual Summer Soiree held at the London Hotel on August 20, 2009 in West Hollywood, California. (Photo by Alberto E. Rodriguez/Getty Images)
This belt has never worked, not in 2009 and not now. We've got a lot of folks here with pale faces and tan legs -- a challenge not totally solved by the passage of time, truly.
Nia Long
WEST HOLLYWOOD, CA - AUGUST 20: Actress Nia Long arrives at InStyle Magazine's 8th annual Summer Soiree held at the London Hotel on August 20, 2009 in West Hollywood, California. (Photo by Alberto E. Rodriguez/Getty Images)
She is a babe. Remember how we all were walking around wearing shoes that looked designed to conceal home-arrest ankle monitors?
Jennifer Morrison
WEST HOLLYWOOD, CA - AUGUST 20: Actress Jennifer Morrison arrives at InStyle Magazine's 8th annual Summer Soiree held at the London Hotel on August 20, 2009 in West Hollywood, California. (Photo by Alberto E. Rodriguez/Getty Images)
Speaking of shoes, these are a snooze. However...this dress appeals to me.
Jenna Dewan
WEST HOLLYWOOD, CA - AUGUST 20: Actress Jenna Dewan arrives at InStyle Magazine's 8th annual Summer Soiree held at the London Hotel on August 20, 2009 in West Hollywood, California. (Photo by Alberto E. Rodriguez/Getty Images)
This whole THING is a snooze -- well, not the color.
Yvonne Strahovski
WEST HOLLYWOOD, CA - AUGUST 20: Actress Yvonne Strahovski arrives at InStyle Magazine's 8th annual Summer Soiree held at the London Hotel on August 20, 2009 in West Hollywood, California. (Photo by Alberto E. Rodriguez/Getty Images)
But this is interesting and also aged well.
Julie Benz
WEST HOLLYWOOD, CA - AUGUST 20: Actress Julie Benz arrives at InStyle Magazine's 8th annual Summer Soiree held at the London Hotel on August 20, 2009 in West Hollywood, California. (Photo by Alberto E. Rodriguez/Getty Images)
Nobody loved Cage Heels more than those of us limping through 2009.
Busy Philipps
WEST HOLLYWOOD, CA - AUGUST 20: Actress Busy Philipps arrives at InStyle Magazine's 8th annual Summer Soiree held at the London Hotel on August 20, 2009 in West Hollywood, California. (Photo by Alberto E. Rodriguez/Getty Images)
This reminds me of why I hated jumpsuits so much at this period in time. It just...feels.... underwhelming on her. This whole thing is so underbaked!
Radha Mitchell
WEST HOLLYWOOD, CA - AUGUST 20: Actress Radha Mitchell arrives at InStyle Magazine's 8th annual Summer Soiree held at the London Hotel on August 20, 2009 in West Hollywood, California. (Photo by Alberto E. Rodriguez/Getty Images)
I think I had the Forever21 dress that knocked off this pattern.
Gabrielle Union
WEST HOLLYWOOD, CA - AUGUST 20: Actress Gabrielle Union arrives at InStyle Magazine's 8th annual Summer Soiree held at the London Hotel on August 20, 2009 in West Hollywood, California. (Photo by Alberto E. Rodriguez/Getty Images)
She looks cute as can be, even with her tiny ankle warming shoes. No notes!
Linda Cardellini
WEST HOLLYWOOD, CA - AUGUST 20: Actress Linda Cardellini arrives at InStyle Magazine's 8th annual Summer Soiree held at the London Hotel on August 20, 2009 in West Hollywood, California. (Photo by Alberto E. Rodriguez/Getty Images)
2009 really WAS peak Cute Little Dress.
Krysten Ritter
WEST HOLLYWOOD, CA - AUGUST 20: Actress Krysten Ritter arrives at InStyle Magazine's 8th annual Summer Soiree held at the London Hotel on August 20, 2009 in West Hollywood, California. (Photo by Alberto E. Rodriguez/Getty Images)
This is, overall, well done.
Jessica Stroup and Shenae Grimes
WEST HOLLYWOOD, CA - AUGUST 20: Actress Jessica Stroup and actress Shenae Grimes arrive at InStyle Magazine's 8th annual Summer Soiree held at the London Hotel on August 20, 2009 in West Hollywood, California. (Photo by Alberto E. Rodriguez/Getty Images)
2009 was ALSO Peak New 90210.
Sanaa Lathan
WEST HOLLYWOOD, CA - AUGUST 20: Actress Sanaa Lathan arrives at InStyle Magazine's 8th annual Summer Soiree held at the London Hotel on August 20, 2009 in West Hollywood, California. (Photo by Alberto E. Rodriguez/Getty Images)
This is fine! 2009 was ALSO Peak Clothes You'd Maybe Seen at a Work Cocktail event.
Miranda Cosgrove
WEST HOLLYWOOD, CA - AUGUST 20: Actress Miranda Cosgrove arrives at InStyle Magazine's 8th annual Summer Soiree held at the London Hotel on August 20, 2009 in West Hollywood, California. (Photo by Alberto E. Rodriguez/Getty Images)
A missed opportunity for lavender shoes!
Lily Collins
WEST HOLLYWOOD, CA - AUGUST 20: Actress Lily Collins arrives at InStyle Magazine's 8th annual Summer Soiree held at the London Hotel on August 20, 2009 in West Hollywood, California. (Photo by Alberto E. Rodriguez/Getty Images)
Hey, look! It's Emily in Paris!
Kat Deeley
WEST HOLLYWOOD, CA - AUGUST 20: TV host Kat Deeley arrives at InStyle Magazine's 8th annual Summer Soiree held at the London Hotel on August 20, 2009 in West Hollywood, California. (Photo by Alberto E. Rodriguez/Getty Images)
This is a very boring choice of bag for a dress that could have carried ANY other color, she should obviously go back in time and FIX THAT.
Camille Guaty
WEST HOLLYWOOD, CA - AUGUST 20: Actress Camille Guaty arrives at InStyle Magazine's 8th annual Summer Soiree held at the London Hotel on August 20, 2009 in West Hollywood, California. (Photo by Alberto E. Rodriguez/Getty Images)
This may need a steam, but it's cute!
Garcelle Beauvais
WEST HOLLYWOOD, CA - AUGUST 20: Actress Garcelle Beauvais-Nilon arrives at InStyle Magazine's 8th annual Summer Soiree held at the London Hotel on August 20, 2009 in West Hollywood, California. (Photo by Alberto E. Rodriguez/Getty Images)
She's less than a year away from finding out that her spouse was cheating on her and BLOWING UP their email address books with the news.
Ron Livingston and Rosemarie DeWitt
WEST HOLLYWOOD, CA - AUGUST 20: Actor Ron Livingston and actress Rosemarie DeWitt arrives at InStyle Magazine's 8th annual Summer Soiree held at the London Hotel on August 20, 2009 in West Hollywood, California. (Photo by Alberto E. Rodriguez/Getty Images)
Still married!
Sofia Vergara
WEST HOLLYWOOD, CA - AUGUST 20: Actress Sofia Vergara arrives at InStyle Magazine's 8th annual Summer Soiree held at the London Hotel on August 20, 2009 in West Hollywood, California. (Photo by Alberto E. Rodriguez/Getty Images)
Close your eyes and imagine Sofia Vergara. This is NOT what you see. Modern Family was set to premiere in less than a month.
Rebecca Mader
WEST HOLLYWOOD, CA - AUGUST 20: Rebecca Mader arrives at InStyle Magazine's 8th annual Summer Soiree held at the London Hotel on August 20, 2009 in West Hollywood, California. (Photo by Alberto E. Rodriguez/Getty Images)
She looks great in this; the color is perf on her.
Sonya Walger
WEST HOLLYWOOD, CA - AUGUST 20: Actress Sonya Walger arrives at InStyle Magazine's 8th annual Summer Soiree held at the London Hotel on August 20, 2009 in West Hollywood, California. (Photo by Alberto E. Rodriguez/Getty Images)
Sonya Walger looks like she's auditioning for the role of a major magazine editor.
Jess Weixler
WEST HOLLYWOOD, CA - AUGUST 20: Actress Jess Weixler arrives at InStyle Magazine's 8th annual Summer Soiree held at the London Hotel on August 20, 2009 in West Hollywood, California. (Photo by Alberto E. Rodriguez/Getty Images)
I've got BIG QUESTIONS about the shoes but embrace that print.
Lindsay Price
WEST HOLLYWOOD, CA - AUGUST 20: Actress Lindsay Price arrives at InStyle Magazine's 8th annual Summer Soiree held at the London Hotel on August 20, 2009 in West Hollywood, California. (Photo by Alberto E. Rodriguez/Getty Images)
She can ABSOLUTELY look back at this with total confidence. It's fab on her.
Jordana Brewster
WEST HOLLYWOOD, CA - AUGUST 20: Actress Jordana Brewster arrives at InStyle Magazine's 8th annual Summer Soiree held at the London Hotel on August 20, 2009 in West Hollywood, California. (Photo by Alberto E. Rodriguez/Getty Images)
SHINY!
Kellan Lutz
WEST HOLLYWOOD, CA - AUGUST 20: Actor Kellan Lutz arrives at InStyle Magazine's 8th annual Summer Soiree held at the London Hotel on August 20, 2009 in West Hollywood, California. (Photo by Alberto E. Rodriguez/Getty Images)
