1995 - Gavin Rossdale

I totally, totally forgot that Gavin Rossdale's hair used to look like mine does when I cut it short.

1995 - Dave Pirner/Soul Asylum

I thought, "Wow, this dude dated a LOT of people in this era," and then realized I was thinking of Adam Duritz of the Counting Crows (HE dated two Friends, and allegedly also Monica Potter, Samantha Mathis, Mary-Louise Parker, Trishelle from The Real World Las Vegas, and... Emmy Rossum???). Dave Pirner, as best I can tell, was just with Winona Ryder for a while. Anyway, Soul Asylum was a big deal for a hot minute.

1997 - Backstreet Boys

The good news for Howie is that his pants are back in style. (That IS Howie in the brown?)

1998 - Britney

Look at this sweet innocent babychild in her Gap khakis.

1998 - Shania

I am reasonably confident Shania still owns this, and would still wear it.

1999 - J.Lo

J.Lo probably does not own any of this, but might miss that bra.

1999 - Nick Lachey

You know this photographer was like, "I HATE WHERE THEY MADE ME STAND."

2000 - Britney

Oh wow, the low-rise lace-up jeans AND the use of a duster as, essentially, a shirt... classic turn-of-the-century.

2000 - Mandy Moore

How far she has come, too.

2000 - Jessica Simpson

I am surprised it took this long for Santa to come down the chimney.

2001 - Missy Elliott

Were those made with a staple gun?

Mariah Carey

Look at that feathered hair. Mild Farrah Fawcett vibes.

Alicia Keys

It's a belt where a belt doesn't go, but maybe it IS actually helping make sure her pants don't sink.

Michelle Branch

I assume her stylist slapped this with a skull and crossbones as a way of telling her NOT to wear it.

O-Town, date unclear (but obviously after 2001)

OH KIDS. I love that this is the Jingle Ball STYLE JAM, also. There is not much style, and probably not a lot of sincere jamming either.

2002 - Destiny's Child

No one escapes the Jingle Balls. Not even the children of Destiny.

2002- Kylie Minogue

I swear, that top could pass for present-day Mugler or Mônot.

2004

The abs! The tights under her jeans! Gwen was just full sartorial madness for a good long while.

Jay Z, no year listed

I am unclear when this was. Informative Caption said it was "The Year 200." That's leaving out some key information, there, pal. I also didn't know Jay Z ever wore Cubs gear? Wasn't his Yankees hat offended?

2004 - Kelly Clarkson

It's such a trip to go back in time and see when they were having Kelly try having an edge. I mean, "Since U Been Gone" and "My Life Would Suck Without You" ARE fantastic songs, but still. She's such a maternal mensch now.

2004 - Vanessa Carlton

Well, look, she SAID she'd walk a thousand miles; it makes sense she'd do it in walking boots.

2004 - Lindsay Lohan

This is a very dated outfit that still truly could have been so much worse.

2004 - Ryan Cabrera

Remember the time he made it really far in Fug Madness JUST on the strength of his hair?

2004 - Hilary Duff

I forgot about her era of many necklaces. And the tight low-rise capris... oh, the errors we made.

2005 - Rihanna

It also just seems impossible that Rihanna was ever this wee child.

2005 - Natasha Bedingfield

The rest of her SHIRT is still unwritten, that's for sure.

2006 - Rihanna

I mean, I'd try on that coat NOW.

2006 - Pussycat Dolls

I forget who every single one of these people is except for Nicole Scherzinger. This is strangely comforting to me -- there is enough meaningless celebrity trivia in my head displacing the things that actually need to be there. This is one LESS piece of trivia in there.

2006 - Brooke Hogan

Yes, in the aughts, someone did try to give Hulk Hogan's daughter a pop career. It was a very weird time.

2007 - The Jonai

Okay, Joe's outfit is genuinely slick, especially for 2007, but LOOK at their junior coifs! We have GOT to go in for a closeup on Nick.

Nick Jonas

This is a 15-year old attempting some real HEY GIRL energy and not entirely succeeding.

2007 - Nat and Alex Wolff

AND THESE TWO. You might remember Nat from Admission and Paper Towns and The Fault In Our Stars, and Alex is in the new Jumanji movies. They were in The Naked Brothers Band on Nickelodeon, and I am the crypt keeper.

2008 - Lady Gaga

And here we have the dawn of Lady Gaga, who is dressed as Superman's Cave of Solace or whatever the hell it's called.

You can see her in there somewhere, behind the eyelashes that she clearly cut off a dish brush and glued to her face.

2008 - Katy Perry

Yes, she absolutely would be dressed as Carhop Santa. (Gaga must have been kicking herself, though.)

2009 - Leighton Meester

I FORGOT THEY TRIED TO MAKE HER A POP STAR.

2009 - Taylor Swift

"I'm STILL a pop star. PEACE OUT AMERICA."

Okay, But What About Jingle Balls of Yore?

I'm SO glad you asked.