Robert Downey Jr.: 30 Years of Red-Carpet Looks
Emily Beck
Published Apr 04, 2026
Iron Man 3 opened this weekend to both box-office and critical success. But had you told anyone fifteen years ago that Robert Downey Jr. would be the face of that franchise, plus an Avenger, it would have sounded like a long shot. Downey’s infamous drug abuse derailed his career for a while — a long while, long enough for People magazine to have two different stories about him called “Hitting Bottom.” But he’s made quite the comeback! Now that he’s Sherlock Holmes, Iron Man, and a hell of a late-night guest, it seemed like the perfect time to go all the way back to the beginning and trace Robert Downey Jr.’s pop evolution, from the early bad-boy era to the modern-day Mr. Charming.
RDJ still wears jazzy jackets and statement glasses, but this is one of the few photos of him with his original teeth.
Photo: Barry King/? Corbis. A...RDJ still wears jazzy jackets and statement glasses, but this is one of the few photos of him with his original teeth.
Photo: Barry King/? Corbis. All Rights Reserved.With Harvey Keitel. Think of RDJ's cigarettes in this slideshow like the silent cat in illustrated children's books. Is he on this page? There he is!
...With Harvey Keitel. Think of RDJ's cigarettes in this slideshow like the silent cat in illustrated children's books. Is he on this page? There he is!
Photo: Ron Galella, Ltd.Anthony Michael Hall, Robert Rusler, and Robert Downey Jr. co-starred in Weird Science. But the real weird science is the variety of complexions on di...
Anthony Michael Hall, Robert Rusler, and Robert Downey Jr. co-starred in Weird Science. But the real weird science is the variety of complexions on display in this one photo.
Photo: Ron GalellaThere are so many eighties things going on here, but the most eighties thing of all is Sarah Jessica Parker's ankle bracelet.
Photo: Ron Galella, Ltd...There are so many eighties things going on here, but the most eighties thing of all is Sarah Jessica Parker's ankle bracelet.
Photo: Ron Galella, Ltd./1987 Ron Galella, Ltd.That's the same jacket on SJP, right?
Photo: Ron Galella, Ltd./1987 Ron Galella, Ltd.At the fifth annual VMAs with Suzanne Vega.
Photo: Ron Galella, Ltd./1988 Ron Galella, Ltd.With Slash, also at the VMAs.
Photo: Barry KingLook closely: That's a Dukakis/Bentsen pin.
Photo: Ron Galella, Ltd./1988 Ron Galella, Ltd.Oy, that beard is brutal. (With 1969 director Ernest Thompson.)
Photo: Jeff KravitzWith Justine Bateman and Leif Garrett, and the same jacket from the previous slide.
Photo: Ron GalellaWith Christian Slater, and a cigarette. And still with that sorry-looking facial hair.
Photo: Ron GalellaYou could swap Bruce Willis, Demi Moore, and Downey's eyebrows, and not even be able to tell.
Photo: Ron Galella/1989 Ron GalellaSJP and RDJ at the Oscars. Aw.
Photo: Barry KingMan, they dated for a long time.
Photo: Ron Galella, Ltd.They probably started measuring time in jackets and blazers. "Today is our ninth jacket anniversary."
Photo: Jim Smeal"Many happy returns of the blazers."
Photo: Jean-Paul AussenardWhite stockings!
Photo: Tom WargackiThe bigger the jacket, the closer to God. Right, Sheryl Crow?
Photo: Jeff KravitzWith his father, Robert Downey Sr. And shorts.
Photo: Time & Life Pictures/Time & Life PicturesThat's his sister Allison Downey, who apparently shared his affection for massive coats.
Photo: Ron GalellaRemember when tinted glasses were a thing?
Photo: Jeff KravitzDon't call it a comeback. Actually, do: It was a comeback, thanks to Ally McBeal.
Photo: Gregg DeGuireAt the SAG awards, with Rob Lowe and the ugliest pair of white shoes in the known universe.
Photo: Ron Galella, Ltd./2001 Ron Galella, Ltd.Singing with Sting, blisfully unaware that his cumberbund (or is that just a belt?) is trying to make an escape.
Photo: LUCY NICHOLSONDowney was presenting Elton John with an award, but they both went home winners.
Photo: Frank MicelottaMaybe Downey got his enthusiasm for tinted lenses from Elton John!
Photo: J. Vespa/Call (212) 686-8900 or e-mail to license WireI...Maybe Downey got his enthusiasm for tinted lenses from Elton John!
Photo: J. Vespa/Call (212) 686-8900 or e-mail to license WireImage images.Now they both have super-thin eyebrows. And you could still switch them.
Photo: Michael Caulfield ArchiveWe're with you, Malcolm McDowell. That hat is a nightmare.
Photo: George PimentelMore tinted glasses.
Photo: Gregory PaceYou can't quite see, but trust us: These glasses are tinted, too.
Photo: J. MerrittStop it! No more tinted lenses!
Photo: Carlo Allegri/2003 Getty ImagesWith Woody Harrelson, Obba Babatunde, and a merciful lack of eyewear.
Photo: Vince Bucci/2004 Getty ImagesDid you know that he released an album in 2004 called The Futurist? Well, he did.
Photo: Kevin Winter/2004 Getty ImagesAnd now we segue into red-carpet-goofball phase. Put up your dukes, etc., along with Shane Black, Michelle Monaghan, and Val Kilmer, promoting Kiss Ki...
And now we segue into red-carpet-goofball phase. Put up your dukes, etc., along with Shane Black, Michelle Monaghan, and Val Kilmer, promoting Kiss Kiss Bang Bang.
Photo: Evan Agostini/2005 Getty ImagesNever doubt RDJ's commitment to sneakers. He wore lavender kicks to his own wedding.
Photo: WireImage HouseMore promotional goofballing with Kilmer.
Photo: Kevin Winter/2005 Getty ImagesFear not, men who struggle to grow facial hair even into their twenties. Whatever patchiness seemed to plague Downey in the eighties and early ninetie...
Fear not, men who struggle to grow facial hair even into their twenties. Whatever patchiness seemed to plague Downey in the eighties and early nineties seems to have resolved itself by 2006. There is hope.
Photo: KMazurThough Keanu Reeves is more than happy to remind everyone sometimes patchiness will always be there.
Photo: VenturelliThe awfulness of the hair doesn't distract from the awfulness of the sunglasses. For someone with a reputation for being handsome and dapper, the man ...
The awfulness of the hair doesn't distract from the awfulness of the sunglasses. For someone with a reputation for being handsome and dapper, the man has had a few red-carpet missteps. (His wife Susan looks nice, though.)
Photo: Scott Wintrow/2007 Getty ImagesThis is better, though it's hard not to look like a dumpy troll hobo next to Gwyneth Paltrow.
Photo: Elisabetta Villa/2008 Getty ImagesOr like a sensible, well-dressed adult next to Jack Black.
Photo: Jeffrey Mayer/2008 Jeffrey MayerRDJ is giving Ben Stiller a run for his money as best-dressed at the Tropic Thunder premiere, but that mustache is a slight negative.
Photo: Kevin Wi...RDJ is giving Ben Stiller a run for his money as best-dressed at the Tropic Thunder premiere, but that mustache is a slight negative.
Photo: Kevin Winter/2008 Getty ImagesDon't be fooled by Jack Black wearing the same lightning jacket twice! This is a different occasion. One where Downey has decided to scrap the 'stache...
Don't be fooled by Jack Black wearing the same lightning jacket twice! This is a different occasion. One where Downey has decided to scrap the 'stache.
Photo: Dave M. Benett/2008 Dave M. BenettThat is a shiny, shiny jacket. But it's better than what Guy Ritchie is wearing.
Photo: Dave Hogan/2008 Getty ImagesDapper effect in full force. If only he'd striaghten Jonah Hill's tie.
Photo: Eric Charbonneau/VF/2009 Getty Images/VFEverything's a little quirky and weird in this outfit, but it works. Except for those G-D tinted glasses, making a reappearance.
Photo: Jason Merritt...Everything's a little quirky and weird in this outfit, but it works. Except for those G-D tinted glasses, making a reappearance.
Photo: Jason Merritt/2010 Getty ImagesGreat, now you've summoned the patchy-beard demon, too.
Photo: Jeff Vespa/2010 Jeff VespaCan't those just be sunglasses? Regular sunglasses?
Photo: Gregg DeGuire/2010 Gregg DeGuireHow come the dog doesn't get to wear a hat, too?
Photo: Gareth Cattermole/2010 Getty Images... Kiss?
Photo: Jeff Vespa/VF11... Kiss?
Photo: Elisabetta A. Villa/2011 Elisabetta A. Villa... Kiss?
Photo: Dave M. Benett/2012 Dave M. Benett... Kiss? (But also, take those glasses off.)
Photo: Epsilon/2013 EpsilonFinally, a kiss. But these molester-style glasses with a slight yellow tint have got to go.
Photo: Alberto E. Rodriguez/2013 WireImageAw. Iron Man hand-warmers.
Photo: David M. Benett/2013 David M. Benett