"Girl, Interrupted" Premiere, 1999

Angelina Jolie, Brittany Murphy and Winona Ryder

This photo is very sweet and touching to me. Who knows how any of these people really got along at the time, but it's a lovely shot. (Winona looks like she cannot believe Angelina just said whatever she said.)

Angelina Jolie

VERY on-brand for Angie -- always, but especially in 1999.

Winona Ryder

Remember what I said about leather? 71% of women under 45 owned an approximation of this look in 1999. Including me.

Clea Duvall and Brittany Murphy

On the other hand, both of these looks feel relatively timeless. There was also an uptick in a sort of 1950s Ladylike Vibe in the late 90s that aged very well -- the accessories are what dates both of these. Brittany Murphy for sure regretted those shoes at some point in this evening because that style was VERY uncomfortable. It asked so much of your toe!

Lenny Kravitz

Mandatory Credit: Photo by Bei/Shutterstock (4371885v) 'Girl, Interrupted' Premiere 'Girl, Interrupted' Premiere 30Kravitz.jpg 12/8/99-Hollywood, CA The World Premiere of Columbia Pictures' "Girl, Interrupted" Lenny Kravitz Photo®Eric Charbonneau/Berliner Studio

I honestly think Lenny Kravitz might BE a vampire? So ageless, so beautiful, so often wearing sunglasses.

Matthew Lillard and Heather Helm

They are still married! I wonder if they both still own these leather jackets....

Kate Hudson

Mandatory Credit: Photo by Bei/Shutterstock (4371885i) 'Girl, Interrupted' Premiere 'Girl, Interrupted' Premiere 15Hudson.jpg 12/8/99-Hollywood, CA The World Premiere of Columbia Pictures' "Girl, Interrupted" Kate Hudson Photo®Eric Charbonneau/Berliner Studio

Real talk: I LOVE this velvet top and wish I currently owned it.

Wilmer Valderama

Mandatory Credit: Photo by Bei/Shutterstock (4371885m) 'Girl, Interrupted' Premiere 'Girl, Interrupted' Premiere 19Vanderama.jpg 12/8/99-Hollywood, CA The World Premiere of Columbia Pictures' "Girl, Interrupted" Wilmer Valderama Photo®Eric Charbonneau/Berliner Studio

Meanwhile, Wilmer Valderama is delighted to be out and about in his overcoat!

Elisabeth Moss

Mandatory Credit: Photo by Bei/Shutterstock (4371885r) 'Girl, Interrupted' Premiere 'Girl, Interrupted' Premiere 23Moss.jpg 12/8/99-Hollywood, CA The World Premiere of Columbia Pictures' "Girl, Interrupted" Elisabeth Moss Photo®Eric Charbonneau/Berliner Studio

And Elisabeth Moss is a CHILD here! (She was only 17; this was also the year she started on The West Wing, so a busy career year for the future Peggy Olsen.)

Rebecca Gayhart and Kevin Williamson

This was right about when Rebecca Gayhart was starring in Williamson's failed show Wasteland, so this was some early PR work from them. (They weren't pretending to be dating or anything; Kevin Williamson has long been openly gay. They were just attending events together.) (She was just about to break up with Bret Ratner here, in fact.)

Kirsten Dunst

Youthful readers, just know this: This was ABSOLUTELY the cutest outfit of 1999 and I myself owned basically all these bits as well and WOULD WEAR THEM AGAIN.