1990: Milli Vanilli
I am coming in HOT here with some Milli Vanilli. Sorry if that surprised you. I blame it on the rain. They both look like they really don't want anyone to ask them any questions, which makes sense NOW.
1990: NKOTB
I can't stress enough how many of us youngsters in 1989 and 1990 were in love with these four. Well, mostly Joey, for me. I look at them now, and they are just such a stunning time capsule. Jordan is basically David Silver before there was a David Silver, and Joey is rocking a Boy George Lite vibe, and Donnie is like, "I'm only 21 but I look like I'm secretly 30."
1990: Bobby Brown
I downloaded this photo a while ago and then his son died. Man, his life has been soaked in tragedy. So... his jacket is awesome and I hope he's okay.
1991: Vanilla Ice
Obviously.
1992: Celine Dion
Ballerina Celine! So innocent.
1999: Will Smith
We didn't have a ton from the 90s for some reason, so suddenly it's 1999. Will Smith won for "Big Willie Style" and is about to stab himself in the armpits.
1999:
Oh Young Britney, I have SO MUCH TO TELL YOU. And you're not gonna like some of it.
2000: Xtina
Xtina was the queen of turning dickeys into shirts.
2000: Brit Brit
This is like the opposite of a bib shirt.
2000: Lou Bega
Do you have Mambo No. 5 in your head now? ... How about now? ... HOW ABOUT NOW???? SORRY NOT SORRY.
Pink
Nope. No envy.
2001; Pink
Gather 'round, Fug Nation. Are these overalls that are missing straps? How are they staying up? What... hath Pink wrought?
2001: Jessica Simpson
SPEAKING OF PINK.
2001: Tiffani Thiessen
I did NOT remember that she had a blond phase.
2001: Cher
ANOTHER unexpected blond phase. They're everywhere. But this outfit looks like Pink designed it.
2001: Britney and Justin
THIS IS WHAT YOU CAME FOR, THOUGH. Surely. This is the most iconically fugly visual feast. Katy Perry paid homage to it at the VMAs, and y'all, I thought that was like two years ago, MAYBE three, but it was 2014. WHAT.
2002: Britney and Justin
True love is when you share the same dye job.
2002: Kid Rock and Pam Anderson
Meanwhile Pammy is wearing a loincloth.
2003: Hilary Duff
WHY do people quit on dresses and think, "I'll just send her a pair of slacks to round this out"? It's not a good plan.
2003: Shania
"Just cinch it," someone said, and Shania took it terribly literally.
Shania
She was right to change, as costumey as this is.
2003: Xtina
Sweetie, when the bib shirts fall apart in the wash, you're supposed to throw them OUT.
2003: Mya
She looks like a brightly painted turtle. I'm a little concerned that the purple circle RIGHT over her pelvis is translucent?
2003: J.Simp
I believe these are what someone in the 70s would have called "snazzy."
2003: Jessica Alba
That's a good outfit. Surprisingly normal.
2003: Pink
THERE we go with the crazy. I knew things couldn't stay staid for long.
2003: Kimberly Stewart
Wow, remember when she was a semi-socialite (she's Rod's daughter)? And did you remember she ended up having a baby with Benicio Del Toro?
2003: Britney
"Weeeeeelll, I asked if it would be sweater weather and my assistant heard 'nether feathers,' and that was that."
2003: Kid Rock and Pammy
ANOTHER de facto loincloth.
2004: Nicolette Sheridan
She is doing a great Britney impersonation here.
2005: Katherine Heigl
Katherine's styling really has always done her dirty. She constantly looks like she's dressing for the day she's like a glam fifty-something.