Mandatory Credit: Photo by Alex Berliner/BEI/Shutterstock (1506830ap)
Charlize Theron and Bill Paxton
'American Pie' Premiere
Neither of these folks are in this movie, and Charlize -- who looks like Peak Prada 1999 (a Prada that I, for what it's worth, was obsessed with) -- apparently cut her bangs with toenail clippers. Even in 1999, I was doubtful about these very short bangs.
Edward Furlong and Natasha Lyonne
Mandatory Credit: Photo by Peter Brooker/Shutterstock (308022c)
Edward Furlong with guest
' AMERICAN PIE' FILM PREMIERE LOS ANGELES AMERICA - 12 JUL 1999
A reminder: Edward Furlong is alive. Also: Natasha Lyonne was credited as "AND GUEST" here, which is absurd! She's IN this movie! Anyway, I would have loved and still might love her skirt.
Tara Reid
Mandatory Credit: Photo by Alex Berliner/BEI/Shutterstock (1506830ab)
Tara Reid
'American Pie' Premiere
Tara Reid is wearing a formal skirt (very 1999), a tank top, and....a tablecloth? I don't know.
Tangi Miller
Mandatory Credit: Photo by Alex Berliner/BEI/Shutterstock (1506830a)
Tangi Miller
'American Pie' Premiere
Tangi Miller was like, "yeah, it's just a movie. I'm going to be comfy."
Dyan Cannon
Mandatory Credit: Photo by Peter Brooker/Shutterstock (308022b)
1999 DYAN CANNON
' AMERICAN PIE' FILM PREMIERE LOS ANGELES AMERICA - 12 JUL 1999
I'd believe you if you told me Dyan painted those jeans herself.
Seann William Scott
Mandatory Credit: Photo by Alex Berliner/BEI/Shutterstock (1506830ag)
Seann William Scott
'American Pie' Premiere
Stifler looks pretty suave here.
Jennifer Coolidge
Mandatory Credit: Photo by Alex Berliner/BEI/Shutterstock (1506830v)
Jennifer Coolidge
'American Pie' Premiere
As does his mom. (Full disclosure, I think I had this dress.)
Jason Biggs and Shannon Elizabeth
Mandatory Credit: Photo by Alex Berliner/BEI/Shutterstock (1506830n)
Jason Biggs and Shannon Elizabeth
'American Pie' Premiere
Shannon Elizabeth's shoe choice has not aged well AND was not well-thought-out at the time! (Jason Biggs looks highly reasonable though.)
Nicholle Tom
Mandatory Credit: Photo by Alex Berliner/BEI/Shutterstock (1506830al)
Nicholle Tom
'American Pie' Premiere
Am I wrong to still love this dress? I might be emotionally still in 1999.
Kerr Smith and someone I can't ID
Mandatory Credit: Photo by Alex Berliner/BEI/Shutterstock (1506830au)
Kerr Smith
'American Pie' Premiere
The sunglasses-around-the-neck is every boy I ever dated in this time period.
Jessica Biel
Mandatory Credit: Photo by Alex Berliner/BEI/Shutterstock (1506830bj)
Jessica Biel
'American Pie' Premiere
July 7, 1999: Los Angeles, CA
Jessica Biel
"American Pie" Premiere
Photo by Alex Berliner ® Berliner Studio/BEImages
I cannot tell for sure, but there's a non-zero chance that she's wearing capri pants.
Traci Bingham
Mandatory Credit: Photo by Alex Berliner/BEI/Shutterstock (1506830aw)
Traci Bingham
'American Pie' Premiere
No lie, but Traci could probably pull those jeans out and wear them now. Which is tough when it comes to denim.
Ali Larter
Mandatory Credit: Photo by Alex Berliner/BEI/Shutterstock (1506830by)
Ali Larter
'American Pie' Premiere
July 7, 1999: Los Angeles, CA
Ali Larter
"American Pie" Premiere
Photo by Alex Berliner ® Berliner Studio/BEImages
I promise you that almost every woman you know who was an adult in 1999 had a pair of these shoes.
Chris Klein and Alyson Hannigan
Mandatory Credit: Photo by Alex Berliner/BEI/Shutterstock (1506830j)
Chris Klein and Alyson Hannigan
'American Pie' Premiere
Alyson Hannigan's handbag has come all the way around to being back in style again.
Soleil Moon Frye and Jason Goldberg
Mandatory Credit: Photo by Alex Berliner/BEI/Shutterstock (1506830s)
Soleil Moon Frye and Jason Goldberg
'American Pie' Premiere
These two were freshly married here and are in fact still married. (Also, proof that Stuart Weitzman did not invent those shoes.)
Ben Affleck
Mandatory Credit: Photo by Alex Berliner/BEI/Shutterstock (1506830y)
Ben Affleck
'American Pie' Premiere
And then Ben Affleck showed up...and also helped me figure out where this premiere was, namely, Universal CityWalk.