1999
Look at these baby children. Ashton had been on That 70s Show for a year, and January was just getting started. Mostly I look at this and think that I cannot believe people were all worked up over Ashton Kutcher. God, remember when all he wore were Ed Hardy trucker hats?!? Anyway.
1999
This photo is hilarious and I hope she has it in a frame in her house (unless she hates him now). Their giant goofy smiles! No one does that anymore.
2000
I almost didn't recognize her here. This was at the premiere of Reindeer Games, and for some reason everyone in this photo behind her looks like a total finance bro.
2001
This movie, Bandits, she's actually IN -- and indeed this dress is a crime. It's very early aughts boutique, though, for sure.
2003
Ultra low rise jeans strike again.
2003
She is in Anger Management, also, which came out right before Love, Actually (which is typically, I think, the first movie people associate with her). Based on the dress, I'm guessing she broke her ribs before the party and had to fashion a crude wrapping.
2003, with Seann William Scott and Alyson Hannigan
This conversation looks JUICY and both she AND Alyson Hannigan need to hang this photo in their homes. Unless they all hate each other now, etc. Alyson is SHOCKED AS HELL and January is clearly going, "MMM HMMM I KNOW RIGHT?" I've decided it's because Tara Reid is wearing something terrible.
2003, with Paris Hilton
Hmm. Do we think THESE two still speak? Do we think January even knew Paris was there? Do we think Paris could look any more baked and friend, and yes, I'm ONLY referring to the aesthetics in that description?
2003, with Josh Groban
I forgot they dated. One of the delights of the world is how funny Josh Groban has turned out to be, but I feel like I've also heard rumors he's not a super faithful boyfriend? Fug Nation, set me straight. Also, she really was in a pro-navel phase here, wasn't she?
2003
"You gave me $15 and a very small mall and dared me to get dressed. TA-DA!"
2003
That's the Love Actually premiere, and I'm pleased she got such a friendly coat for it.
2004
I had NO IDEA she is in "Dirty Dancing: Havana Nights," and also, this entire outfit is ADORABLE. It's the first one I've seen on her that feels styled from head-to-toe, but more in the way that she bought the whole thing off a store mannequin. It's so so adorable.
2004
Aw, baby's first Needs a Slight Hoik.
2005
She was in two episodes of Huff, and I assume that's why she attended the Globes. This might have been better without the dismal rose. It's a bit flat, but might have been sweet without that misguided flourish, though she could use it as an emergency hanky.
2005
You can banish her navel but YOU CANNOT BANISH HER ABS ALTOGETHER.
2005
We really sincerely did the worst things with pants in the aughts. THE WORST. (Please note, I did not do this with pants. I want to absolve myself of this particular sin.)
2005
It's interesting that at Cannes, typically a wild one, she went with something fairly understated and glam. But she's also still a relative rookie at this point so maybe that was the right play.
2005
The mismatch between dress and shoes here is substantial.
2005
And, enter the phase where belts turned up in situation where they were not wanted or needed.
2005
A ribbon belt AND formal shorts? it's a 2005 jackpot.
2006
GO HOME, belted tunics, YOU'RE DRUNK.
2007
January has worn some sincerely amusing casual looks over the years, and this is very high on my list of belly laughs. THAT HAT. I hope she recreates these on instagram for us all. The addition of the cap is nonsensical regardless, but it would have made slightly more sense without the black piece over her blouse. This is not what the concept of "layering" is supposed to mean.
2007
This was the debut of Mad Men, I believe. It's clearly a price-range upgrade, but still a little drab and it doesn't QUITE suit her.
Mad Men
Pause to remember how well cast and beautifully styled she was on this visual feast of a show.
2008
I believe this is Armani, and I'm into a lot of it. But not the top ruffle. It looks like when someone tries to tease tissue paper out the top of a gift bag.
2008
Oodles of buttons!
2008
The day Miss Havisham discovered blue jeans was the happiest of her life.
2008
Well. The dressmaker was correct that the existing neckline was too low, but I don't know if a black dickey was the solution.
2008
Yep. She tried it. She tried it all.
2008
Well. This takes "longline bra" to a new level.
2008
Now i understand her current penchant for adorable caftans and robes.
2009
Very pretty!
2009, in Versace, with Sigourney Weaver
I wish this didn't look so crinkly. But I am happy to see Sigourney make a cameo in this slideshow. The world always needs more Sigourney Weaver.
2009: in Andrew Gn
I'm always begging people to wear Andrew Gn, though this one was never at the top of my list. I kind of like it, but I think she needed to lean a bit harder into the Queen of the Nile vibe with stronger makeup and a cool updo.
2009
WOULD YOU LIKE TO FEEL OLD TODAY?
2009 in Versace
This might've needed a small necklace. It's very well done otherwise, though.
2009
When you see THIS bodice, it especially highlights how well done the previous one is.
2010: Lanvin
She is determined to put SOME kind of band or wrap or adornment on her head, isn't she?
2010: Versace
I love this whole dress EXCEPT for the weird pointy boob hats. Well, and it needed better shoes. Those clonky black ones are distracting.
2011 in Versace
Her head looks AMAZING in this. The bodice looks like she's been painted with a red V. She's like a high-fashion hula girl stuck to your dashboard.
2011 in Carolina Herrera
This is SO much lovelier.
2011 in McQueen
We're into the highest of high fashion now. I don't think the head styling QUITE works with this, but damn, the dress is cool.
2012
I love the art deco sleeves on this.
2012 in Wes Gordon
I can sort of see from this why Wes Gordon was chosen to take over Herrera eventually. I think it needs some tweaks to truly work, but I like the idea.
2012 in Zac Posen
There's a lot of interesting work here, but the left side just ends up looking like a math error more than a choice.
2012
I assume this collection was called Angry Butterfly.
2011
Oh no.
2012
This looks great being blown around AND probably also was awesome when it wasn't. I love the collar.
2012
This is a very good Versace indeed.
2012
This is pretty good, but also illustrates the challenge of having things fasten up the front. The line often comes out wonky.
2012
The kleenex on her hem is really messing with the vibe.
2013 in Prabal
And now she's dressed AS the box of Kleenex.
2013
She made a noble Fug Madness run thanks to this.
2013
This is very apt for the Punk Met Gala, and also very funny, seeing her standing in front of Kim Kardashian's epically awful Givenchy.
2013: in Givenchy
This dress is some of Riccardo Tisci's best work. I think that it's either someone else's dress, or that it needed more styling juice in order to truly sing, because it's not quite working. But the skirt is just so pretty.
2014
This is DEFINITELY Fug Nation approved.
2014 in Roksanda
This looks for all the world like it ripped around her shoulder, and not like it was meant to have a hole there. But in fact it is NOT a hole; it is the tail of her braid. Losing the braid would have helped so much.
2014 in Prabal Gurung
I love this dress and the whole look, but would have scraped back the bangs and hoiked it.
2014 in Hugo Boss
I WANT to like this, but her head-styling is really throwing me for a loop.
2014
ROCK N' ROLL. I'm into it.
2015 in Sandro
I can see where this is going, but think the bodysuit needed not to be black.
2015 in Roland Mouret
This jumpsuit is slick though. Yes, I just said that about a jumpsuit. I KNOW.
2015
Why does this dress look like it's opening its mouth?
Shiny and good!
2015
Gorg.
2015 in Burberry
This whole thing is GREAT except for the Glamour Don't bars she's wearing on her feet.
2015
Another win.
2015
And how good is THIS? Five in a row! Things are looking up!
2015 in Prabal
WOMP-WOOOOMP.
2015
This is so Gumby and so sassily wacky and while I don't LIKE IT, I do enjoy that she's coming across like she's in on how wacky it is.
2015 in Lela Rose
However, I will always scream at see-through pants. Your legs are not gift baskets! Leave the cellophane at home!
2015 in Disaya
The skirt says "ROYAL WRITING FLUID" so it's... ink, I guess? This whole thing is kind of fun though until the pirate treasure she's wearing on her feet.
2016 in Altuzarra
This didn't need to have it both ways. Pick one length or the other, Joseph.
2016 in Schiaparelli
Oy, none of this works. Her great face gets completely lost.
2016
She historically does love fringe.
2016 in Disaya
If she'd worn this TODAY I would have assumed she'd quilted it herself during a Covid funk.
2016
Today's special is fresh squeezed boob.
2017
Well. I guess if you're going to do the socks and sandals like a kid at church, you might as well go full barrette too.
2018 in Coach
Lordy. STOP IT, COACH.
2018 in Moschino
If you're at a Moschino show with a person in a lion costume who looks like a depressed cereal mascot, then what the hell, ditch the pants.
2019
She looks like a disco paratrooper, and I can't tell if she has ANY idea that her underboob came as her plus-one.
2019
Big Villain Energy.
2020, in Alessandra Rich
And this is the last time we saw her on a red carpet. It's a very charming, slightly retro Ladies Who Lunch vibe. I assume once the world starts turning again, she's going to come out with fug guns blazing and go full Noted Kook, though. Or maybe I just hope that.