The Evolution of Gwyneth Paltrow’s Sometimes-Chic Style
Photo: Getty Images
Gwyneth Paltrow is having a big month: Iron Man 3 hits theaters this weekend; her second cookbook, It’s All Good, was just released; in spite of that optimistic title, Star’s readers recently voted her “most-hated,” ahead of lady-puncher Chris Brown; and then, a mere eight days later, People named her Most Beautiful. So, it’s official: Gwyneth does everything. This is a woman who wears the nickname GOOP with a measure of actual dignity, and sported a cape to the Oscars with regal panache. But what is her track record really? We dug through old red-carpet photos and found that, in terms of fashion, Gwyneth has historically gotten it so very wrong a lot more often than she’s gotten it right. Click through the slideshow to see her style missteps through the years. Do they humanize her, or just irritate you further? Either way, let’s be honest: If it will give us her abs, we’re totally buying that cookbook.
When: March 1994
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Why: Gwyneth’s first trip to the Oscars.
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What: Well. This is an inauspicious beginning. Photo: Ron Galella, Ltd./1994 Ron G...
When: March 1994
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Why: Gwyneth’s first trip to the Oscars.
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What: Well. This is an inauspicious beginning. Photo: Ron Galella, Ltd./1994 Ron Galella, Ltd.
When: July 1995 - March 1997
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Why: Various Movie Premieres of the Brad Pitt Years.
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What: If the couple that got matching highlights together ...
When: July 1995 - March 1997
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Why: Various Movie Premieres of the Brad Pitt Years.
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What: If the couple that got matching highlights together stayed together, these two would be married right now. Alas, that wasn’t written in the stars. But that doesn’t mean we can’t make a horrified face at that insane satin bathrobe Gwyneth is wearing as a coat — accessorized with a cigarette, no less. Photo: Ron Galella
When: Early 1996
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Why: The Golden Globes and the Oscars, as half of the Golden Couple.
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What: Gwyneth looks relatively normal, actually, thoug...
When: Early 1996
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Why: The Golden Globes and the Oscars, as half of the Golden Couple.
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What: Gwyneth looks relatively normal, actually, though this is the first sighting of the strappy, slightly saggy V-neck silhouette that she’d famously wear a few years later to accept her own Oscar. We are more distracted by the fact that Brad Pitt looks exactly the same at both events. Photo: Ron Galella/WireImage
Kevin Mazur/WireImage
When: December 1995 and July 1996
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Why: The Met Gala and the premiere of Emma, respectively.
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What: Someone is serving some Calvin Klein/Carol...
When: December 1995 and July 1996
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Why: The Met Gala and the premiere of Emma, respectively.
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What: Someone is serving some Calvin Klein/Carolyn Bessette Kennedy tank-dress realness with a side of quarter-life ennui. Photo: Kevin Mazur/WireImage
When: December 1995, September 1996
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Why: The Twelve Monkeys premiere, and the VMAs.
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What: Nowadays, if you pop out in one velvet suit, much ...
When: December 1995, September 1996
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Why: The Twelve Monkeys premiere, and the VMAs.
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What: Nowadays, if you pop out in one velvet suit, much less two, someone is going to make a joke about a fire sale at Prince’s house. But in the mid-nineties, these Gucci suits were the bomb — and the beginning of Gwyneth’s long affinity for Tom Ford. Photo: Ron Galella
When: January 1997
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Why: The Golden Globes.
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What: Based on that unfathomable hair, we are concerned someone told her it was the Golden Glutes...
When: January 1997
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Why: The Golden Globes.
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What: Based on that unfathomable hair, we are concerned someone told her it was the Golden Glutes, prompting her to arrive after doing a thematic workout of 200 squats and hamstring curls. Photo: argaret Norton/NBC/NBCU Photo Bank via Getty Images
When: April 1998
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Why: The Sliding Doors premiere.
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What: This just feels like one of those outfits that couldn’t have happened at any other p...
When: April 1998
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Why: The Sliding Doors premiere.
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What: This just feels like one of those outfits that couldn’t have happened at any other point in time. Photo: Scan Room/2008 Getty Images
When: June 1998
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Why: The premiere of A Perfect Murder.
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What: Like the previous look, this is very much Of Its Time, but with prophetic eleme...
When: June 1998
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Why: The premiere of A Perfect Murder.
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What: Like the previous look, this is very much Of Its Time, but with prophetic elements: what appear to be random translucent parts throughout (maybe from the flashbulbs), and then a somehow-again-trendy sheer insert at the bottom to display those hideous sandals.The shoes of the late nineties/early aughts — like the leisure suit before them — are warts on history. Our grandchildren are going to have notes. Photo: Ron Galella
Ltd./WireImage
When: December 1998 and January 1999
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Why: Myriad premieres of Shakespeare in Love.
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What: You can basically trace Gwyneth’s thought process o...
When: December 1998 and January 1999
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Why: Myriad premieres of Shakespeare in Love.
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What: You can basically trace Gwyneth’s thought process on the Shakespeare in Love premiere junket through these three looks, and this is how it goes: too many nipples, not enough nipples, just enough nipples. She’s like the Three Bears of Boobs. Not for nothing, the white gown and coat foretell her white Tom Ford gown at the 2012 Oscars, but mercifully she 86ed the choker for round two. Photo: Diane Freed/Getty Images)
Barry King/WireImage
Antony Jones/UK Press via Getty Images
When: March 1999
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Why: Gywnnie won Best Actress for Shakespeare in Love at both the Oscars and the SAG Awards. She also apparently attended the Ac...
When: March 1999
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Why: Gywnnie won Best Actress for Shakespeare in Love at both the Oscars and the SAG Awards. She also apparently attended the Academy Awards nominees luncheon looking like a college student late for her sociology final.
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What: The pink Ralph Lauren dress has gotten a lot of flack over the years for not fitting particularly well, but it’s definitely an iconic look — possibly for being somewhat divisive. As for that SAGs dress, given that it looks a bit like an Elizabethan nightgown, she at least gets points for adherence to theme, but demerits for being Anne Hathaway’s precursor in the “nipple or darts?” debate. Photo: Ron Galella
Ltd./WireImage
Kevin Mazur/WireImage
When: January and February 2000
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Why: The Golden Globes, and the Talented Mr. Ripley premiere.
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What: Certainly there are times for the surpri...
When: January and February 2000
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Why: The Golden Globes, and the Talented Mr. Ripley premiere.
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What: Certainly there are times for the surprise deployment of a formal pant. The Golden Globes is not one of those times — or at least, not if the pants you’re choosing belong to an ensemble fresh off the clearance rack at Express. As for the Ripley outfit, we’re sorry Gwyneth went to such trouble to match her shoes to her shiny trousers. But the scaly shirt and orange makeup alarm us just as much. Was she afraid no one would look at her, with Matt Damon and Jude Law in the house? Photo: Kevin Mazur/WireImage
Mark Cuthbert/UK Press via Getty Images
When: March & July 2000
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Why: The SAGs, and the premiere of Butterfly.
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What: The outfits aren’t great — this is Attempted Pearly Thin-Str...
When: March & July 2000
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Why: The SAGs, and the premiere of Butterfly.
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What: The outfits aren’t great — this is Attempted Pearly Thin-Strapped V-Neck, Part II — but it’s the styling that’s truly egregious. Orthopedic flip-flops with a ball gown? And crimped hair? Can we blame it on the millennium scrambling her mind-software? Photo: Ron Galella
Ltd./WireImage
Evan Agostini/ImageDirect
When: September 2000 and January 2002
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Why: The Toronto Film Festival; a Dior event.
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What: We had to group these together, because they’re hi...
When: September 2000 and January 2002
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Why: The Toronto Film Festival; a Dior event.
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What: We had to group these together, because they’re hideous and niptastic on their own, but together it’s like you’re getting punched in the face by brass knuckles that spell out the word TACKY. Where is the GOOP newsletter about her secret past as the tightrope walker in a soft-core circus? Photo: J. Vespa/WireImage
BertrandRindoff Petroff/Getty Images
When: November, 2001
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Why: The premiere of Shallow Hal.
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What: Gwyneth recently noted that she doesn’t remember much about Shallow Hal. ...
When: November, 2001
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Why: The premiere of Shallow Hal.
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What: Gwyneth recently noted that she doesn’t remember much about Shallow Hal. We hope that includes this. Photo: Ron Galella
Ltd./WireImage
When: March 2002
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Why: The Academy Awards.
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What: Gwyneth — who has been making a lot of trips down the memory lane of her wardrobe lately — a...
When: March 2002
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Why: The Academy Awards.
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What: Gwyneth — who has been making a lot of trips down the memory lane of her wardrobe lately — also recently said that, in hindsight, she wishes she had worn a bra with this Alexander McQueen. We can’t say we disagree. Photo: Frank Micelotta/Getty Images
When: July/August 2004
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Why: The Anchorman premiere and the VMAs.
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What: Summer movie season tends toward the casual, but there’s never been a...
When: July/August 2004
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Why: The Anchorman premiere and the VMAs.
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What: Summer movie season tends toward the casual, but there’s never been a legitimate excuse to shrink all your vests to boob-mashing widths and bust out capris that technically might be just very long shorts. And, obviously, we couldn’t let the Summer of 2004 pass without mention of The Cupping Incident. Presumably Gwyneth was so fixated on us being aware of her ancient healing hobbies that she made sure the outfit wouldn’t distract us from the bruises. Photo: Kevin Mazur/WireImage
Jim Spellman/WireImage
When: February 2005-February 2007
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Why: Two Oscars and a Golden Globes.
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What: The dusty rose frock from the 2007 Academy Awards is love...
When: February 2005-February 2007
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Why: Two Oscars and a Golden Globes.
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What: The dusty rose frock from the 2007 Academy Awards is lovely, and the lighter pink one would be acceptable if it fit — which it certainly does not. As for the white Jane Austen getup, we have bowed to our kinder instincts for once and given Gwyneth a pass for going Full Milkmaid while pregnant. Fetuses love calcium. Photo: Carlo Allegri/Getty Images
Kevin Winter/Getty Images
Frazer Harrison/Getty Images/2007 Getty Images
When: April 2008
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Why: The press tour for the first Iron Man, which was basically a long trip to Leg City.
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What: We LOVE the sassy bob, and ...
When: April 2008
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Why: The press tour for the first Iron Man, which was basically a long trip to Leg City.
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What: We LOVE the sassy bob, and that tuxedo jacket is adorable. But that’s about it. One dress is shrink-wrapped, one looks like a bleak doily that got censored at her pelvis, and the last is glaring back at us sullenly. We prefer to live by the mantra, “Don’t wear a mouth where your crotch is.” Photo: Chris Jackson/Getty Images
Sean Gallup/Getty Images
Stephen Lovekin/Getty Images
When: May and November 2008
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Why: The premieres of Two Lovers, a movie we never would have remembered, ever, were it not for this slideshow...
When: May and November 2008
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Why: The premieres of Two Lovers, a movie we never would have remembered, ever, were it not for this slideshow.
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What: That navy blue sack is depressing and wrinkled, but it’s a veritable celebration of sartorial delights compared to the black and white ensemble, which appears to be specifically designed to showcase Gwyneth’s panties. Photo: Francois Durand/2008 Getty Images
When: February 2009
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Why: The Grammys.
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What: Everything was going so well ... until Gwyneth decided that the best way to accessorize he...
When: February 2009
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Why: The Grammys.
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What: Everything was going so well ... until Gwyneth decided that the best way to accessorize her sparkly dress was with robotic limbs, like C3P0 with hypothermia. Photo: Kevin Mazur/2009 Kevin Mazur
When: November 2010
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Why: Country Strong’s Nashville premiere and the CMAs.
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What: We’ve now entered the era of Gwyneth-as-musician, and she’s...
When: November 2010
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Why: Country Strong’s Nashville premiere and the CMAs.
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What: We’ve now entered the era of Gwyneth-as-musician, and she’s re-embraced everything peekaboo, as if that were price of admission. The black dress — a high-fashion ode to having one’s chest cracked — takes absurd pains to show off her belly button. The triangular cutout on the other is boxy and unflattering; from the side, it almost looks like she’s got sweat-stains on her illusion netting, which is only okay if you’re sitting in the Kiss and Cry with your coach, waiting to find out if a botched toe-loop has ruined your life.
When: November 2010
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Why: A Country Strong premiere.
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What: Repeat after us, Gwyneth: “My body is not a shoe, so it should not have laces.” Ph...
When: November 2010
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Why: A Country Strong premiere.
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What: Repeat after us, Gwyneth: “My body is not a shoe, so it should not have laces.” Photo: Larry Busacca/2012 Getty Images
When: February, May, and September 2011
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Why: The Oscars, Met Ball, and Emmys.
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What: Gwyneth, she of the finely tuned physique, often does be...
When: February, May, and September 2011
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Why: The Oscars, Met Ball, and Emmys.
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What: Gwyneth, she of the finely tuned physique, often does better when she keeps it simple but sleek, without any gimmicks like laces or belly shirts. Ergo, that Emmy dress does her no favors. Later, at the Met Ball, it was hard to look away. Photo: Larry Busacca/2012 Getty Images
When: February 2012
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Why: The Academy Awards.
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What: It takes a lot of self-confidence to work a cape at the Oscars quite like this (by ...
When: February 2012
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Why: The Academy Awards.
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What: It takes a lot of self-confidence to work a cape at the Oscars quite like this (by which we mean flawlessly). It will be one of her most memorable outfits, for all the right reasons. Photo: Kevork Djansezian/2012 Getty Images
When: May 2012
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Why: The Met Ball.
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What: Speaking of self-confidence, here’s your lesson in not being too cocky. On the red carpet, Gwyneth s...
When: May 2012
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Why: The Met Ball.
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What: Speaking of self-confidence, here’s your lesson in not being too cocky. On the red carpet, Gwyneth said she hadn’t tried on this dress until moments before leaving the house, and it shows: She’s oozing boob, the length is terrible, and the pockets look like spangly novelty potholders. We could swear she’s trying to apologize with her eyes. Do you think Miuccia Prada apologized with a case of wine? Photo: Larry Busacca/2012 Getty Images
When: April 2012
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Why: The Iron Man 3 premiere
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What: Now that “side-butt” is a thing (sigh) trust Gwyneth to trot out the most directional, m...
When: April 2012
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Why: The Iron Man 3 premiere
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What: Now that “side-butt” is a thing (sigh) trust Gwyneth to trot out the most directional, most editorial side-butt in history. You can’t ever accuse her of doing things half-assed — pun totally intended — and this look is certainly attention-grabbing, if also somewhat insane. And, ultimately, that’s the thing. Some may vote her most-hated, and others might dub her most beautiful, but no one will ever call her most boring. And that’s something. Photo: Jason Merritt/2013 Getty Images
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