1985

We begin with arguably the most relatable photo in the bunch: A 13-year old Gwyneth at an event with her mom, in a doily collar and Jessica McClintock-esque dress, smiling while her mom appears to be bumping into something.

1994

And then we leap straight to 1994, very early in her career (bit parts only, I think?), where she's hanging with Leo. The woman in the background appears to be wishing that texting and/or cameraphones had been invented at this point.

1994

She's at the Oscars here, hanging with James Ivory, as you do. (She's in his Jefferson in Paris, which came out in 1995; they may have been filming, or about to film.) She should be about 22, if my math is right, which is certainly old enough to take your bedsheet to a tailor and have something better done with it.

1995

She definitely had a thing for simple satin back then.

1995 with Brad

Even in coat form. (Seeing her with a cigarette is so jarring to me. I mean, for all I know she's smoked forever, but the Gwyneths I remember the best are the macrobiotic one and the GOOP one, and neither of them seem very nicotine-adjacent.)

1995 Costume Institute Gala

She also cherished a tank dress, I guess. And wraps.

1995, with Brad

This is SLIIIIGHTLY more elaborate. But the real star of the show are Brad's oval sunglasses, which he truly loves.

1995

I can't tell if she is displeased that he won't take off his shades, or that they are going to see Waterworld.

1996

"He won't stop wearing them AND his suit doesn't seem to fit. I despair. I despair so hard that the waist of my dress is at underwire-level."

1996

GP also does love a very bare top -- people (I am one of them) questioned the fit of her pink princess Oscars gown in 1999, but this neckline isn't that dissimilar. So it might not be a fitting error so much as a preference.

1996

I am never sure about the shirt crinkled under the blazer, but this is very cool, and in 1996 felt chic as hell. It probably still would.

1997

"I was not planning to come until ten minutes ago."

"Who's even nominated for these this year? MADONNA? Dang, I told her I saw Evita, I should get on that."

1997

They broke up shortly after this, I think, but it's the era in which Brad and Gwyneth most resembled each other.

1998

Later in 1997 she started dating Ben, which means she was his Globes date in 1998 when he and Matt Damon won for Good Will Hunting. Her grow-out is adorable, and Ben REALLY likes her ears, as you'll see.

1998

I like Gwyneth in suits. I wish she did it more often.

1998

The lighting in these photos is crackers. Here, you'd swear this frock is navy blue...

... but now it's either grey or brown? (This was Great Expectations, so yes, that's Ethan Hawke pretending to hide under her pashmina.)

"Ben's here and HE thinks my dress is red, so another round over here please and keep them coming!"

We covered the Armageddon premiere earlier in the pandemic, but of course I had to go there again. Those SLIDES.

1998

That lipstick is so perfect. She should wear THAT more often, too. I'd love to shorten the dress a bit, and... is it slightly sheer?

1998

I think we all had this outfit in 1998, and many of us wore it with those super thick Nine West Cloud 9 wedge slides.

1998

"I just want you to know that your ear and your freefloating belt are both perfect."

1998

And then KABOOM she's also got a random fur stole?!? This is at a Dior show; maybe Dior just went a little nuts on her.

1998

And now we have Shakespeare in Love's premiere, and I did not ever remember that she went sheer for it. It's very... ethereal? 

1999

I think this photo was misdated as a Globes pre-party from 1997 when it should be 1999 -- timeline-wise, that makes a lot more sense. Regardless, Ben is whispering sweet nothings again, or snacking, or whatever he does.

1999

There is something so surprising about her wearing, essentially, a twin set and rumpled skirt to what would turn out to be one of the biggest nights of her life.

"Ignore Matt Damon, you hear me? NOBODY will invent a way for the photos of this dress to live online forever, and so no one will remember how crinkly it was."

with Cameron Diaz

"Oh, CAMERON, what are YOU wearing? And where did I leave my shoes? THIS NIGHT, I'm telling you."

1999

This -- purely coincidentally, as it's just a coat over a dress -- has shades of the famous Tom Ford cape dress she will wear in 2012.

This forgettable dress may have been picked before she realized she was a frontrunner. Also, that's Kelly Preston and Tom Sizemore over there, right?

"Ben, just promise me that if the cast wins, you won't do anything crazy with the trophy."

And, scene.

1999

Honestly, this all felt sort of Fine For 1999 but the shoes are so bizarre.

1999 in Ralph Lauren

This still sits a little low on her, I think, but I go back and forth on it as a whole and today I'm feeling kindly disposed.

"It's okay, Gwyneth. Who cares if pople don't love the dress. Because we will be TOGETHER FOREVER."

1999

She's had those wraps, twisted around her hands, in so MANY of these shots and they have to have been annoying to carry everywhere. (This also would have been slicker without the midriff. I would say it's so 1999, but it's BACK, and she could recycle this easily.)

1999

This is really good. I hope she kept some of these.

1999

Wear it again, Gwyneth! Someday there will be another charity thingamy in The Hamptons.

2000

Maybe leave this one in the past.

2000

This is a still from Bounce, but the pants on Ben demanded to be seen.

2000

I see what she's going for here, and the top is funky at least. I think she did her blush in a dark room, though.

2000

And pink pants! It's an experiment that did not flop as badly as I feared -- pointy beige boots were all the rage then -- but, spoiler, we have some rocky times ahead with trousers.

2000

Crimping irons DO need to stay in the 80s where they belong.

2000 in Calvin Klein

This seems SO casual by today's Oscars standards.

2000

This looks like she bought one-third of a gown at auction.

2001

"Ha ha ha, I know, the cotton-candy machine just EXPLODED before I could run!"

2001

This is very Your Sexy Cello Teacher.

2001

I am not sure WHAT the deal is with this dress, which is apt, as the premiere is for Shallow Hal and I do not know what the deal was with that movie either.

2001

Gwyneth's brief tango with amnesia meant she forgot both about proportions AND about what belts do.

2002 in McQueen

I just love this photo. Her face says, "I know what the captions are going to be. Trust me. I know." I feel like... if the dress ITSELF had been even remotely attractive, the sheer aspect of it would have been easier to forget.

2002 Venice Film Festival

This was quite a rebound.

2002 in Stella (I think)

I wonder how many of her bad pants Stella made.

2003

In which Gwyneth learns she is not impervious to the perils of satin.

2003

I don't THINK this was a costume party?

2004

One cannot plan what one's body is going to do while pregnant, but it seems like this dress was always going to be a dangerous boob proposition.

2004

Okay, THIS outfit. First, it's not great, but she'd had Apple two months before this so I'm sure she just wanted to be comfortable. Second, it's infamous because it showed off all the bruises on her back from when she did cupping.

2004

Oh, why not, I might as well show you. She knew everyone could see them, so see them we shall.

2004

I don't have a dress credit on this. Is it Vivienne Westwood, I wonder? It looks like either a haphazard one, or a very hasty copy of one.

2004

Ohhhhh dear. Wide-leg business capris.

2005 in Stella (I think)

I hope she was not still lactating at this point, because OUCH.

2005 in Stella

I can't tell if these are the same pants from two slides ago, or not, but... close enough to count as making the same mistake twice.

2005

And there are more!

2005

And more AGAIN, though these are on the overlong side. This whole outfit is really a stunning mess. NONE of it works, and none of it works together.

2005

This is a much better take.

2006

This feels very Jane Austen.

2007 in Zac Posen

Those cap sleeves are pretty, but I don't think that bodice is Zac's best work. I do at least REMEMBER this dress, though.

2008

Somehow I had forgotten this one. HOW IS THAT POSSIBLE. It's very Blake Lively to me.

2008

This is quite cool, though.

2008 in Gucci

This is a wine bag.

2008

GOOP, you look like an unmade bed.

2008

I will be haunted by this Rorschach blot.

2008

That's rather a lot.

2008

I just feel like this entire dress was designed by someone who doesn't know hw to sew.

2008

I never knew a jumpsuit would be such a welcome sight.

2008

ANOTHER Rorschach. I see a giant heart over her crotch.

2010

Did someone give Apple the hot glue gun again?!?

2010

We just revisited this, and it's.... you know, still fine. We'll forget it again.

2010

Ah, formal shorts. What times we had.

2010

This dress was such an optical illusion -- I remember thinking that her skin there was part of the backdrop, and that tricked me again today.

2010

"Ribs: A tribute."

2010

"Betty Draper: A Tribute."

2010

"Flesh Neckties: A Tribute."

2011

"Please don't make me wave any higher than this. It won't go well."

2011

I THINK this is Michael Kors? It's pretty darn good.

2011 in Calvin Klein

This is MOSTLY good, but I don't fully get the hip thingamy. Is it a brooch, do we think? Although wouldn't that dig in?

2011

Well, she wore a casual long-line turtleneck with a skirt way back in 1999, so maybe this is her reaching her long-held goal of turning it into couture.

2012 in Kors

This ink blot is ANGRY EYES, right?

2012 in Tom Ford

For me, I think, this is the best thing she's worn, but I wish so much she'd gone with the red lip that she's pulled off so well other times.

2012 in Prada

It's an apron, friend. An apron.

2013

It's an armpit cravat, friend. An armpit cravat.

2013 in Valentino

Was this the year where she complained afterward about how boring the Met is? Her approach TO the Met is boring, so maybe the twain there is never meant to meet.

2013

I think this is separates, and MAYBE should have been a jumpsuit?

2013

For a fashion awards show, this seems awfully like one of those Summersalt bathing suits worn under a random skit. I know Summersalt didn't exist back then, but boy, they are all over my Instagram now.

2013

Here is a palate cleanser.

2013

She looks like she's a cheerleader for First Communions.

2013 in Antonio Berardi

I was so on board with the top of this dress...

... but then it all collapsed into nonsense.

2013

This works.

2013

And so does this.

2014 in Prada

THAT is stunning. That is in her top three.

2014 in Roland Mouret

I'm confused by a lot of this. The shoes are so aggressive with it, and the top is just... I feel like I'm staring at the top of her Spanx, but I'm NOT; it's just another part of the dress, I believe.

2014

"I don't know. The lady at the store said everyone is wearing them."

2014

"Oh, good," I thought. "More suits, please, Gwyneth."

2014

AND THEN. Also, I pulled these photos and then STILL got tricked and forgot the random cutout was there.

2015 in Michael Kors

This fitting went awry, I think.

2015

Her head looks GREAT here. The dress feels a tad dated. 

2015 in Gucci

I find this quite kicky.

2015

That's a bit Nightie.

2015

She wore that to give a speech on the Hill, and it's so bizarrely boxy and slouchy to me for that.

2015 in Cushnie et Ochs

That bodice has more twists than Lombard Street.

2015

This is an odd one. From the front it just looks like maybe it's too big...

But then from the side, you can see PART of it is fitted to her and the rest is blousy on purpose. I'm not sure it worked, exactly, but the color is neat.

2015

And then, my favorite photo of 2015. This jumpsuit is so hideous and she looks SO THRILLED.

2015 in Valentino

It's a nice enough tent... but an expensive, expensive tent.

2015

There has definitely been worse.

2015: Ralph & Russo

I really did not like this at the time, but with the benefit of gentler hindsight, I find it charming? It's a little silly, but she carries it. Also, I know she gets way wackier.

2015

At the time, I wrote that this felt sort of blandly like a template she followed, and in compiling this slideshow I realized it's VERY VERY much like the thing she wore in 2013 that I called "First Communion Cheerleader." It is not the same, but it's SO close. Weirdly so. Maybe she gave the other one away and regretted it.

2016 in Stella

I appreciate that she matched her boots to the free potholders.

2016 in Emilia Wickstead

We didn't think it could get worse than the ruffled jumpsuit, but it sincerely may have with this.

2016 in Gucci

This is dramatically fun, though.

2016 in Gucci

And I am surprised to find myself digging this.

2016 in Prada

I hope someone brought some strong tape to lend her.

2016

Cheesecake on the lanai, anyone?

2016

Chanel is truly not her aesthetic.

2017 in Kors

She's like a silver version of the backdrop.

2017

That's... a lot of lace, Gwyneth. It's twee. It's a tweever dream.

2017 in Calvin Klein

Again... the theme was Rei Kawakubo, and you don't HAVE to do it, obviously, but... we know NOW that Gwyneth is capable of going over the top and I wish she would have at the Met, which CRIES OUT for wild interpretation.

2017

Now THAT is a great suit, with NO secret peekaboo holes.

2018

Did they steal that fabric from Lanz of Salzburg?

2018

This is amusingly disco.

2018 in Dior

I don't know if I ever saw this without the cape on over it, but the cape itself is so pretty that I'm not sure I mind? What's under it also looks like it was nice, from here, so... let's decide it's not secretly made of hair.

2018 in Alex Perry

I do not know what the twin butler's pulls offer, exactly. Other than perhaps twin butlers.

2018

At the time, I wrote, "You can't hem it WHILE you're wearing it," and I stand by that.

2019

........... I just.... comfort, but.... it's.............

2019 in G Label

This is a GOOP-made situation that feels a bit knocked off from her closet... which is, I think, kind of the point of that line?

2019 in G Label

This reminds me of a chic-er, better-executed version of the satin bag she wore waaaaaay at the top of this adventure in 1994.

2019

Lovely.

2019 in vintage Valentino

NUTTY AS A TUB OF JIF.

2019

And then this is so staid. Her pendulum swings FAST.

2019

This dress looks like it was inspired by belly-button piercings.

2019

This was sort of a casual, nothing outfit -- it's perfectly fine and does the job for a party at your friend's jewelry store, all is well and good. But then she wore the skirt again...

2019

And it did NOT GO AS WELL. The swater really needed to fit.

2019 in Chloe

The theme of this Met Gala was NOT "Lullabye and Good Night," so I don't get this.

2020 in Fendi

If she is capable of THIS, can she not go wild at a Met Gala?!?

2020 in Ralph & Russo

Or this! She looks like she's there to honor Liberace.

2020

This is the last time we saw her before Covid swept us all away. Given that it's attempting to be sheer and feathered and floral all at once, I can only imagine what else she had up her increasingly kooky sleeves for 2020. I have my issues with Gwyneth, but that doesn't mean I wasn't rooting for some REAL fashion tomfoolery from her. Maybe someday.

It's a Brief Fashion History of GOOP

Minus the "brief" part.