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1999: Jennifer Aniston

Mandatory Credit: Photo by Berliner Studio/Shutterstock (790373c) Jennifer Aniston 5th Annual Screen Actors Guild Awards, Los Angeles, America - 07 Mar 1999

Okay, we're not getting RIGHT to the chase, because I decided to go in chronological order. This was obviously in vogue at the time because about two months earlier Keri Russell wore a similar theme to the Golden Globes, though Jen took it to an extra extreme, REALLY picking one that looks like she made the top out of a cloth napkin. Lisa Kudrow back there looks like she's worried the restaurant they snatched it from will show up and ask for it back.

Lisa Kudrow

Mandatory Credit: Photo by Bei/Shutterstock (790373bf) Lisa Kudrow 5th Annual Screen Actors Guild Awards, Los Angeles, America - 07 Mar 1999 March 7, 1999 - Los Angeles, CA. Lisa Kudrow . 1999 5th annual Screen Actors Guild Awards at the Shrine Auditorium. Photo®Berliner Studio/BEImages

She looks very simple and cute, though. I like the bob on her.

Mandatory Credit: Photo by Bei/Shutterstock (790373er) Cast of 'Friends' 5th Annual Screen Actors Guild Awards, Los Angeles, America - 07 Mar 1999 March 7, 1999 - Los Angeles, CA. David Schwimmer, Lisa Kudrow, Jennifer Aniston, Courteney Cox Arquette, Matt Le Blanc & Matthew Perry. 1999 5th annual Screen Actors Guild Awards at the Shrine Auditorium. Photo®Berliner Studio/BEImages

They negotiate in harmony, they dress in harmony.

2000: Kudrow, David Schwimmer, Aniston

Mandatory Credit: Photo by Araldo Di Crollalanza/Shutterstock (318278g) Lisa Kudrow, David Schwimmer and Jennifer Aniston SCREEN ACTORS GUILD AWARDS, LOS ANGELES, AMERICA - 2000

This is Jennifer's Office Space-era hair, right? The anti-Rachel. They all look fine, but boy, if there is one consistency in Jennifer Aniston's life, it's adherence to a minimalist look.

2000: Courteney Cox

Mandatory Credit: Photo by Araldo Di Crollalanza/Shutterstock (318278d) COURTENEY COX SCREEN ACTORS GUILD AWARDS, LOS ANGELES, AMERICA - 2000

You know, for as dated and AGES AGO as 2000 feels in some slideshows, there are a few outfits that really could still work today. Like Lisa's 1999 black dress, or this one, or the one on the next slide...

2003: Lisa Kudrow

Mandatory Credit: Photo by Alex Berliner/BEI/Shutterstock (408925aj) Lisa Kudrow The 9th Annual Screen Actors Guild Awards at the Shrine Auditorium, Los Angeles, America - 09 Mar 2003

I love this on her, and what a great color. For all Friends's flaws, one of them being how flat-out mean Phoebe veered at times, I thought she handled that part with really expert comic timing. I always feel like she's the unsung castmate -- even though she won two SAGs and an Emmy for the part. I think it's because she was the least titillating in terms of personal gossip, so it may have felt like no one was talking about her in a global sense, even though she did collect those awards.

Matt LeBlanc

Mandatory Credit: Photo by Matt Baron/BEI/Shutterstock (408922ag) Matt LeBlanc THE 9TH ANNUAL SCREEN ACTORS GUILD AWARDS AT THE SHRINE AUDITORIUM, LOS ANGELES, AMERICA - 09 MAR 2003

But sincerely, what are these. Did he get his pupils dilated right before the ceremony, and pull over at a gas station to grab whatever sunnies were still on the rack?

Matthew Perry

Mandatory Credit: Photo by Matt Baron/BEI/Shutterstock (408922ap) Matthew Perry THE 9TH ANNUAL SCREEN ACTORS GUILD AWARDS AT THE SHRINE AUDITORIUM, LOS ANGELES, AMERICA - 09 MAR 2003

"Could there BE more regrettable sunglasses than Matt's?" Well actually, Chandler... possibly.

Schwimmer

Mandatory Credit: Photo by Kim D Johnson/AP/Shutterstock (6428870b) ALAPONT SCHWIMMER Actor David Schwimmer, of the television comedy "Friends," arrives with Carla Alapont at the 9th annual Screen Actors Guild awards in Los Angeles SCREEN ACTORS AWARDS, LOS ANGELES, USA

A cream/white tie with this suit is a bold move, but I think the wrong one.

Courteney and Jen

Mandatory Credit: Photo by Peter Brooker/Shutterstock (408921dj) COURTENEY COX AND JENNIFER ANISTON 9TH ANNUAL SCREEN ACTORS GUILD AWARDS, LOS ANGELES, AMERICA - 09 MAR 2003

Courteney's whole ensemble is so underwhelming, and Jen just looks like her dress is on backwards. I was working on a whole "I'll be there for boob" parody of the Friends theme as sung by her dress strings, but it fizzled. I think that's for the best.

Lisa Kudrow

Mandatory Credit: Photo by Jim Smeal/BEI/Shutterstock (444841x) Lisa Kudrow THE SCREEN ACTORS GUILD AWARDS, LOS ANGELES, AMERICA - 22 FEB 2004

Sure! It beats underboob.

2015

Mandatory Credit: Photo by Broadimage/Shutterstock (4381624el) Jennifer Aniston, Justin Theroux 21st Screen Actors Guild Awards, Arrivals, Los Angeles, America - 25 Jan 2015 21st Screen Actors Guild Awards

And then we skip all the way ahead to 2015, which seems wrong but that's what turned up in the search. I guess Jen took a ten-year break from the SAGs. She was nominated this year for Cake, and the frock was one of her few departures from monochromatic neutrals. I'm halfway here for it, but I suspect she may not have known it was translucent, as I myself didn't notice that I can see her underwear until I looked at this for the third or fourth time. Surprise Sheers are the worst kind. At least with the overt ones, you know the wearer is fully on board.

Joey, We Need to Talk About Your Shades
They don't make anything hotter.

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