Gwen Stefani
This is perfect on Gwen. I love this era of Gwen. I wish the current Gwen would dig this up and wear it again.
Lindsay Lohan
I truly, truly had to double check my eyesight that this was Lindsay, and not her mother Dina.
Jessica Simpson and Nick Lachey
These two were two months away from the separation that would become their divorce. Jessica stood glued to him the entire time and I wonder if she hated the front of her outfit.
Sincerely, this is the ONLY photo I could find of her facing forward. She looks SO begrudging. And as if she really lost track of her layers. And kind of like a waitress at a theme restaurant about sexy pirates.
Not sure why she was so much more forthcoming with the BACK of this, unless she ripped it walking away from the limo and no one told her.
Rihanna
Rihanna would wear this today, and she'd do it at 9 months pregnant.
Fergie
I'm sure I disliked this at the time, but now I find it fairly charming. IS it charming? Or have I just seen too many things in the last 20 years?
Destiny's Child
The Children of Destiny look like they're modeling the latest in Prom gowns from bebe.
Kirsten Dunst and Orlando Bloom
These two presented together, and were promoting Elizabethtown. Her dress looks a little wonky from this angle, which is a bummer...
... because it's SO GOOD from this angle. Slouchy and chic and sparkly and perfect. The foot shoes are creepy -- who knew those were happening so far back in time? -- but otherwise, I'm in, and I hope she still owns this.
Kelly Clarkson
Kelly won for "Since U Been Gone," CORRECTLY. She looks cute but I've always loved her most as a brunette.
Kristin Cavallari
Imagine going back in time and telling her she'd be marrying Jay Cutler. "The Vanderbilt quarterback?" she'd say. "That guy's NEVER gonna make it."
Jamie Foxx
He and Kanye were nominated this year for "Golddigger," which is, sadly, a timeless banger. Kanye really destroyed his legacy. His OWN, not Jamie's. Jamie is fine.
Jay-Z
Oh, I have a LOT of advice for this man if we were to time-travel. I would not give him any sartorial help; he doesn't need it here.
Alicia Keys
That's quite boring. But also inoffensive. And in 2005, that's basically the JACKPOT.
Jessica Alba
Another shockingly reasonable ensemble that somebody could bust out today.
Shakira
Why the pants, Shakira? What are they POSSIBLY adding except the optical illusion that your legs are pegs?
Nelly Furtado
More normalcy! I don't remember 2005 being this chill. I also love that she went ham on the accessories. It might be too much but that also probably means it's just enough.
Ashlee Simpson
Sanity prevailed here too. WHO KNEW.
Joss Stone
That is just so much denim.
Joss Stone
I can't even tell if those are truly low-rise or if the weight of them is just dragging them south.
Jordan Knight
The New Kids are always welcome on our Block.
Amerie
Wikipedia tells me she's releasing a new album soon. I welcome it! "Take Control" just came up on my shuffle and it holds up.
Jeremy Piven
Entourage had just started a year prior, so he was at Peak Douchecanoe here.
Eva Longoria
This looks like she's wearing scrubs made of satin (and heavily taped to her chest). Also, the tall hair made me giggle. It's like an Amy Winehouse tribute, except I'm not sure she'd have heard of Amy. yet.
Lizzie Grubman
Ah, Lizzie, the most misguided tan in town. (She's in the center.) In 2002, Lizzie, a PR person in NYC, famously hurt 16 people in The Hamptons when she intentionally backed into a crowd -- allegedly while yelling at them for being white trash -- and she ended up in jail for a month. Naturally, the world rewarded her with a TV show about her PR firm.
Hilary Duff
I mean, MAYBE she's standing up straight, and she's just tilting her head down. CHIN UP, HIL. Also your hair is confusing.
Jeff Gordon and Ingrid VandeBosch
I completely forgot this man ever existed (he was a racecar star). He and Ingrid are still married. They announced their engagement at a croquet event, as you do.
Jesse McCartney, Katie Cassidy
I had to check and make sure he's still alive, because I think I confused him with Aaron Carter. Please stay safe, Jesse, I'm not trying to hex you.
Eric Roberts
Such long, flowing locks.
Ciara
I see it NOW, but I'm not sure I would have recognized her? Not because I think she did anything to herself -- to me it's just maturity + different eyebrows.
Snoop Dogg
Mr. Dogg, naturally, arrived on -- not even really in -- a yellow convertible. He looks dapper. I wish he had not recently said all that dumb shit about being traumatized by two female characters in "Lightyear" having a baby together.