1998: with Dule Hill
These two dated on The West Wing. I don't know if they ever dated in real life, but they are CERTAINLY very good friends. She apparently wrote in her book that Dule thought she was making a mistake marrying her first husband, so when he did the reading, he did a very pointed one and punctuated it with a lot of sighs.
2000, with Lindsay Sloane
Look at these two Aughtsy children. Gabrielle's outfit has stood the test of time better, but it's amusing that they accidentally semi-twinned their outfits.
2000
That shirt could ALSO have another tango, if she still has it, although the pants might be better left on the hanger.
2001
This was absolutely 2001 office attire.
2001
This is another one she hopefully kept.
2001
This top ALSO unfortunately would not make anyone bat an eyelash today. I am glad she has chosen to banish it, though.
2001
That's very fun.
2002
And that's, you know, fine!
2003
Wow, remember Rock & Republic? They used to do whole fashion shows. One year, we went and the entire Gossip Girl cast was in attendance, including Rufus Humphrey, and it just... felt so right.
2003
Strange Invisible Perfume is quite a title (I feel like if perfume is strange, you are doing it wrong?) The company still exists, on Abbott Kinney in Venice, and makes "real botanical fragrances with layers of aromatic nuance, wildcrafted essences, and mysterious technique." SOLD.
2003
I feel like... bodysuit OR sarong, no?
2003
I remember SO MANY outfits from this time that had the tight skirt and blousy top. MEMORIES.
2003
That's very pretty, and well-accessorized with those earrings.
2004
I am unclear on why the two halves of this dress are different-ish. An ode to fraternal twins?
2004
I believe Yoanna House wore a version of this in red/orange the night her ANTM win aired. Which was ALSO in 2004.
2004
We just saw her in this color in our BET Awards flashback, in 2002 -- a pic I meant to pull again, but forgot until just now, and then... might as well link it. Anyway, that deep hot pink is phenomenal on her.
2004
This is theoretically all well and fine, but I feel like it's sagging around her pelvis.
2005
The multiple flashbacks to our going-out clothes from this era are truly a nostalgic ride.
2005
YEP.
2005
This dress was just never going to work, anywhere. I don't even think it tried that hard.
2005
Better! But those criss-cross necklines always wig me out a little.
2005
I also applaud the days of GIANT purses on the red carpet. It's practical! We have STUFF! We need to carry it!
2005
This is again well-accessorized to make it feel a bit more special than would be on its own merits.
2005
It was obviously Vein Appreciation Day.
2005
Did this need a necklace? Maybe -- I know, get ready -- instead of the bracelets?
2005
From her giant green purse to that teeeeeeny little capsule. You could fit like 20 of those inside the other.
2005
But THAT purse RULES. In fact, I love this entire outfit.
2006
And this one, except for the shoes. The orange and turquoise, with the gold clutch, are superb.
2006
Sorry, Gabrielle. It just looks too pinchy.
2006
I do NOT remember this era of knee-length tight short. Perhaps I blotted it out? Because there's these...
2006
... and THESE. Which are really harshing the buzz of everything else she's doing.
2006
Gorgeous.
2006
Also VERY cute.
2006
Three in a row!
2007
FOUR.
2007
Well, all streaks have to come to an end, and this one did so with what looks like a very long piece of gaffer tape.
2007
This DEFINITELY needs a statement necklace.
2007
I thought this was a romper for a second, and I feel like Imaginary Romper Syndrome is a death knell for any outfit.
2008
She's at the Kentucky Derby here, working a great hat.
2008
That neckpiece is part of the dress, right? Regardless, it's perfect.
2008
As is this entire thing.
2008
AND this. We're on another hot streak.
2008
Four in a row AGAIN. That has to be a record.
2009
Is it punting if I give this a quarter point for not being TERRIBLE and mostly just needing a hoik?
2009 in Tracey Reese
I can live with this!
2010
And I full-on love this. All of it.
2010
This MIGHT be by Rachel Roy? I'm not sure. The color is good but it's a bit twisty in parts, a technique I prefer in mysteries.
2011
I would have gone with a different shoe, I think, but I can't be mad at this frock.
2011
Another super cute one.
2011
And THIS color is ALSO a win, but the dress again has a bit too much stuff floating around that it might not need.
2011
I like to think that woman is texting the Jessica to her Heather across the venue, all, "I'm sitting next to Gabrielle Union and WOW is she gorgeous and WOW is that a bad jumpsuit CAN YOU SEE THIS?"
2011
Perfect.
2011
That must be Missoni, right? It's a little loosey-goosey up top but looks comfy for summer.
2011
An ode to a Coldstream Guard hat.
2012
She is feeling this, and rightly.
2012
Too many triangles.
2012
But this is GREAT! The shoes with it! The pattern! The sunglasses! Yes.
2012
I sense another hot streak.
2013
Yep. (The texture on this, or the appearance thereof, is awesome.)
2013 in Marc Bouwer
So cool, and I think JUST about as short as it could go.
2013 in Miu Miu
She seems unconvinced. She is right.
2013 in Miu Miu
I mostly like this, but don't think it actually NEEDS to be transparent in any of those places.
2014 in Jerome C
This is stunning enough that the sheers get a pass.
2014
Great dress, and be still, my heart, about that bag.
2014 in Prada
The good news is, every time she sneaks a passed app, she can check her teeth in her skirt.
2014 in D&G
This is.... unmemorable but fine.
2014
Thigh-high boots are rarely the answer, I find.
2014
It is the lipstick of my dreams, atop a dress that might be an accidental ode to laddered panty-hose.
2015
2015 in Zac Posen
And a PLUMMY version. That's excellent, albeit surprisingly simple from Zac for Fashion's Biggest Night. I said at the time that Dwyane Wade looks like a dignitary from a very small but powerfully wealthy principality, and I stand by it.
2015
Straight sunshine.
2015 in Gauri & Nainika
This is like the more successful reboot of the whit gown she wore in the 2012 section.
2015
Is that just a backwards cardigan?
2015 in Halston
That is slinky and great.
2015 in Sophia Ka
And here, another cute day dress.
2015 in Prabal
AND AGAIN.
2016 in Lela Rose
Oh wow. I like this basic idea but my eyes are REALLY struggling with the one boob that looks like it's in the middle of trying to clone itself.
2016 in Prada
Well, the drama factor is high, but so is the choking risk.
2016 with Melissa Harris-Perry
That pattern is perfect, though.
2016 in Sophie Theallet
Why even MAKE a skirt at that point.
2016 in Hugo Boss
Pretty, but droopy.
2016
I never clicked with the trend of slacks that had built-in table linens.
2016
I want to tweak this a bit so that it sits a WEE lower. The drama of it is good, though.
2016
Those shoes make people's feet look like they're holding classified information that's been redacted.
2016
This is making me think too much about bras and such.
2016
Romany Malco seems tickled by the thought of a shoulderless jacket.
2016
SHRIEK. Oh my goodness. This is what you'd get if you tried to get an alien to design a football uniform by playing a game of telephone.
2016
It's a halter AND a turtleneck. It's two necks in one.
2016 in Naeem Khan
Naeem has done a lot of prettier work, but she looks good in it, at least -- she's helping him out.
2016
There is no way that fabric is breathable. Or even possibly fabric.
2016 in Rodarte
"Miss Havisham? No, dear. It's Miss Ravish 'Em."
2016
Oh, but I adore this.
2016 in Marc Jacobs
I enjoy the two patterns on this, but I wish it were a WEE less of a sky-high slit.
2017
This would have been great if the designer had quit before he/she glued on the cargo pockets.
2017
Heart eyes.
2017, with Garcelle Beauvais
Overlong Nipple Zippers is my next hit album.
2017
It's an unremarkable jumpsuit, but that last black jumpsuit she wore was remarkable for the wrong reasons, so: a victory.
2017 in Gabriela Hearst
The bottom of that coat is super.
2017
This is very theatrical. It has a real Beyonce vibe to it.
2017 in Balmain
The best things here are her hair, and his shoelaces.
2017 in Lanvin
There is perhaps a REASON we don't see much Lanvin anymore.
2017 in Valentino
Ooooh. Yes.
2017 in Ports 1961
She is so merry, but that is a blanket-cum-outfit, right?
2017 in Rodarte
Whereas here, she's giving Model Face, but in an ensemble I would be more excited about.
2017 in Valentino I think?
This was at a Valentino party to which everyone else wore Valentino, so this PROBABLY also is? She looks a bit like an avant-garde camp counselor.
2017 in Berluti
Her head looks amazing. I don't like the outfit, but the whole effect is of a '70s glamour that is definitely transportive.
2017 in Dion Lee
Wait... why does it button if...
2017 in Gaultier
And a Fug Madness run was born!
2017 in Stella
High-waisted velvet pants are a bold gamble, but am I crazy to think this paid off?
2018 in Gabriela Hearst
This doesn't really fit, but hey, she won!
2018
This is from her New York & Company line, and while the coat is perfectly fine, obviously I am very into the striped dress.
2018 in Stella
That is a very surprising shirt dress, but she looks adorable.
2018
I'm sure in 2018 we all thought, "Business sweatpants? Why?" And now that we are all at home and more of us are doing business while in sweatpants...
2018 in Prabal Gurung
This did not really bespeak the Catholic Imagination, per se, but she did at least look gorgeous in it.
2018
Super cheery.
2018
I like so much of this, except for the bit where it looks like it's falling off on top.
2018 in Stella
This fabric from Stella got a LOT of play. I believe this was the only version we saw that had knee windows.
2018 in Valentino
Love.
2018 in Marc Jacobs
It is really too bad the CW's Dynasty -- which, yes, is still on -- cannot afford to bring her in as Dominique Devereaux, because she could fill Diahann Carroll's pumps with GUSTO.
I MEAN.
2019 in Pyer Moss
Pyer Moss was inspired to make this (2018) collection when he researched the same book that inspired the movie Green Book, which won the Oscar a month or so after this photo was taken. < href="https://www.elle.com/uk/fashion/a23049074/the-pyer-moss-show-was-held-in-weeksville-one-of-americas-first-free-black-communities/">What he was doing here -- where he took that inspiration, and where he held the show -- is incredibly powerful and still apt.
2019 in Valentino
Boxy, but fine.
2019
So pretty.
2019 in Dundas
Something about the design plus the way she's standing makes it look like her arms are growing out of her abdomen.
in Miu Miu
I am SURE you assumed this was Coachella. IT WAS NOT. (It was Miu Miu's resort show, which I guess... wanted to be Coachella.)
2019
Her experience on AGT sounded like a nightmare, and I appreciate how much she threw herself into it anyway, because she is a freaking professional. This is adorable.
And this, sculptural Kleenex, handy in case a contestant makes you misty.
2019
There is something poking sideways out of her bust that I do not think... is actually her bust.
There was one week where everyone brought baby pictures, and she carried one of hers, but had this dress made of Dwyane's. It's so funny and good.
2019 in The Blonds
Vampy!
She is the person who skydives into the stadium for the Marching Band finale and THEN grabs an instrument to play an encore.
That's good!
This shirt feels like an homage to a sea creature.
2019 in Marco de Vincenzo
"It needs more... details," the designer said, "but I'm out of thread. Where's my glitter glue?"
2019
I appreciate the leopard shoe with this.
2019
None of these things go together, but... it's chipper?
with Jessica Alba
They look great -- both of those skirts are big wins.
Again, both excellent.
That's ... less thrilling? Gabrielle matched her shes to her bra straps, which is impressive.
I would like this a lot better if I could parse it.
2019 in Christopher John Rogers
I wish for gold shoes. And MAYBE slightly longer pants? But that's so fun. And again, that great pink she wears so well.
2019 in Ralph Lauren
VERY well played.
2019 in Miu Miu
I can't tell if this was for an early morning show, or leaving a late-night show. I hope the latter? Mostly, I just really feel the wine cardigan.
2020 in Acne Studios
PANTS WHERE.
2020 in Ralph & Russo
At the time Jessica said she wants them to wear these for a lavish vow renewal. I agree.
I like this, but the pattern is also JUST busy enough that my eyes are blurring before I get a great sense of its shape.
in Giambattista Valli
And here's the last photo we have. Her dress is an ode to tissue-paper flowers, but you cannot argue with that face.