1994: with Joey Lawrence
So, per Entertainment Tonight, these two DID INDEED date -- she wouldn't turn 16 for another four months, and he had *just* turned 18. Sometimes Memory Lane bears TREMENDOUS FRUIT. Look at them matching. They're like a Gap ad.
1995
A year later, still 16, she wore this to the Under Siege premiere and looks for all the world like she is auditioning to anchor the nightly news. That is some real Professional Helmet Hair.
1995
She is giving me serious Emily Ratajkowski vibes here -- facially, I mean, not fashion-wise. In terms of what she's wearing, she looks like so many of the girls I went to school with in Miami in ninth grade, who were dressing like tiny adults.
1996
Here, she's at Fashion Week, supposedly?!? I am crushed that I can't see the rest of the outfit. I assume it's overalls. What if it's overall-SHORTS, or a jumper of some kind?!? This whole outfit is when people stop being nice and start being influenced by The Real World.
1999
This is so frumpy. She was 20. I find it strangely endearing that she, too, finds this shit hard to do when it's her own self.
2000, with Brendan Fehr
In that same 2013 interview, she listed this as the worst thing she'd ever worn on a red carpet. Bless her heart, she remembered it exactly. I don't suppose one would soon forget.
2001
This is BETTER and she looks the correct age, but I also think Target sells that as a shower curtain.
2001
This was inexplicably labeled "Haley Joel Osment," which is a truly amazing mistake. And unlike the previous photo, this one -- in which Katherine is 22 -- features her dressed like a much older socialite.
2004
I believe those boots match the shade of her sweater? Which of course is showing bra, because 2004.
2004
Here, Katherine is at the ABC Upfront for Grey's, which was picked up in 2004 to premiere in early 2005. But did you know she also shot another pilot? Romy and Michele: In The Beginning was about Romy and Michele deciding to move to LA after high school when they saw Pretty Woman, and... DECIDING TO BECOME PROSTITUTES but then chicken out on their first attempt. WHAT. It did not get picked up, so to speak. Also this mismatched outfit really brings back memories.
2005
We're now done with the first Grey's season, it was popular, and she's got a suit she could wear right now. Some pieces are timeless, Katherine.
2005
THIS PIECE IS NOT. Seriously, that is... the teeniest micro bolero I have ever seen.
2005
She really loves a cropped cardi. And a cropped trouser. Neither are worth her devotion.
2005
She wore that to Tommy Hilfiger in 2005. It looks like her jacket is failing to cover the Eye of Sauron.
2005
I'm not sure if she's wearing this stole, or if it's trying to hold her back from entering this event in that skirt.
2005
This vintage-looking dress had potential, but I think it just isn't quite her color palette. She should have wrapped it up and left it on Zooey Deschanel's porch. Better shoes might have helped.
2006
This is not terrible?
2006
This dress did not need TWO dropped waists.
2006
First cropped cardigans, and now cropped TIED cardigans. I guess that tracks. One cannot help one's passions.
2006
This is all very... burnished. It's not the worst she's worn, but it doesn't seem fit correctly.
2007
I am fumbling for my sunglasses.
2007
I think we need a red lip and a necklace here, but at least she doesn't NAB.
2007
This is pretty on her. Everything is finally harmonizing here.
2007
That's not bad either, but is there an extra bow stuck to her hip?
2007
"NO. NOBODY GO INSIDE." (Interestingly, in 2008, she took a LOT of heat for complaining that her character in this movie and indeed a lot of women in it were portrayed as fun-sucking and joyless and shrewy, and that the dudes all got to be likable and fun-loving, and people pilloried her for it. here's the thing: Women ARE often portrayed as shrewy and fun-sucking in Apatow movies. She is allowed to be grateful for the doors it opened for her while also reflecting on what bummed out about it.
2007
This is the year she won her Emmy, and she's got good head-styling happening here, but the dress looks a little wrinkly and then just like a heavy curtain. It didn't survive the limo ride, really.
2008
Sure! One of her better looks.
2008
This has a real Jennifer Lawrence In The Red CK Tube Dress look to it, even though that actually hadn't happened yet.
Usa Academy Awards - Feb 2008
This is one of my favorite dresses on her, but dear LORD, did her makeup artist have the lights off?!?
2008
If the Real Housewives existed then (DID THEY? Time has no meaning but I don't think so?), this would look like an audition photo.
2008
Cute coat! I feel like Jessica had a coat like this. Am I hallucinating, Jessica?
2009
It's hard to stand in front of a photo of yourself in which you are wearing a better dress. This is VERY Discount Bridesmaid, although high marks for the necklace.
2009
I like this one better, probably just because it's green. This movie was a freaking mess. I stumbled upon it on cable the other day and it didn't go well.
2010
Here, she is trying boots that look like someone drew them onto her legs.
2010
This was a tough hair day. A tougher shoe day.
2010
I actually love this dress on her, and the shoes are also a kick. But WHAT IS HAPPENING ON HER HEAD. When the outfit isn't aging her, the hair is. It' just very... "Hello, I'm Stockard Channing, and I'm reading for this role in Up Close and Personal."
2010
This return to blond was particularly harsh. The dress is fine? It's ALSO a little bridesmaid-y, to be frank.
2011
This all seems acceptable!
2012
This seems lightly inspired by a slideshow of Kate Winslet.
2012
RED ALERT! SUNGLASSES THAT NEEDED TO BE LEFT AT HOME!
2012
This dress is VERY sexy and good, but I want a do-over on this hair and makeup also.
2013
This is what she was wearing at the J.Mendel show when we spoke. She looks very cute!
2014
She has gone back to her comfort space: cardigans.
2014
This is not bad on the surface, but it also looks like something you would send to, like, Meryl, or Dame Helen, and she was 35 and this was 2014 and things were FOR SURE out there with a bit more personality. It also doesn't fit great; the arms look uncomfortable.
2014
Sheers were an overcorrection.
2015
This is pretty good though! I say that as someone who doesn't always love the vomiting hem, but sheesh, this comes across here like fresh air.
2015
ACK. So pinchy.
2017 in Blumarine
This is another one that just doesn't fit superbly, and her hair and makeup isn't making any of it pop.
2017
Cute dress, cute shoes, but again kind of a dated-looking bob. She is giving me Megyn Kelly vibes.
2017 in Lanvin
This has a flourish or two too many, but I get the style she's trying, and I'm not mad at the concept. I MIGHT be mad at the shoes, but just for lack of imagination. One thing at a time, though.
2018
She wears a lot of white, and I don't think I would go in that direction myself? Also this skirt looks like it's on backwards. Maybe that's a good visual metaphor on which to end. Happy birthday, Katie! There are bigger things in life than getting the red carpet right, and may you revel in all of those today.