Oscar Flashback Fuggery: What The Stars Wore Ten Years Ago


When you begin to despair of the fashions of today, sometimes it’s fun to hop in the DeLorean and see what ills were perpetrated in the past, to remind you that it wasn’t so dreamy then, either. Wait, that’s depressing: “It’s always been bad!” There was, as with today, plenty of good as well. In fact, in digging around for this, I remembered that the 2006 Academy Awards brought SO MUCH stuff: It was the rebirth of pockets in gowns; it featured couples who are no longer together (RIP Heath Ledger); and it was the height of Bai Ling and Paris Hilton. It might ALSO have been the birth of the Sheers, courtesy of Stephanie Seymour. Bless you, 2006. #neverforget

[Photos: Getty, Fame/Flynet]

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Comments (163):

  1.  attica
    +18

    Rachel Weisz is such a lovely, ethereal thing. And yet, I still want her to sidle over to Michelle Williams and borrow her lipstick.

    • Joo
      +1

      Also, she did not age

      • jeansheridan
        0

        Possibly the power of being married to Bond. James Bond. Daniel Craig doesn’t really do it for me, but he clearly does something for her.

        I love how she somehow has a better career in her forties than in her twenties. She went from British arm candy to serious actress during a decade when most actresses fade away (looking at you Aniston, Roberts, Ryan, and Julia Roberts).

    • Kirsten
      0

      She’s not a thing!

  2. AJ
    +94

    That Michelle Williams look is THE yellow dress. Iconic. But oh that picture makes me sad.

    • welshforjohn
      +7

      Does anyone else think her lipstick was a little TOO red though? I think it was just a bit too strong. I would’ve gone for a lighter red or maybe even pink. Her lips are reminding me of the Joker’s in this pic (I know. Sorry, y’all).

      • Teri
        +35

        I think the red lip is perfect! The whole look is so elegant, and the red lipstick to me makes it fun too.

        • welshforjohn
          +2

          I love the gown, jewelry and hair. The lip being too red is just a quibble I have. I think it’s clashing with the yellow a bit because it’s too dark. I just would’ve preferred it in a lighter shade of red, that’s all.

          • GP
            +5

            I think that color dress needs the red lip to bring some life to the face. She would look dead without it. I do love a red lip though…

            • greatwhitenorthchick
              +10

              I, too, loved the red lip. Gorgeous. The only other yellow dress that comes close, imho, is Nicole Kidman’s Asian-inspired yellow frock, from an Oscar ceremony back when she was still married to Cruise.

        •  Stavra
          +3

          I agree. That exact red lip is what made the whole look so perfect. Definitely not pink, that would be awful!

      • Lily
        +5

        NO WAY, not a pink lip with that dress!

        With a dress that shade of yellow, you need a red lip to really make the most of it. Michelle knew that, and look at her. She’d be perfection if she showed up in that dress to the Oscars, even now.

    • Lily
      +1

      I know what you mean, AJ, that picture makes me sad too :(

  3. Nora
    +20

    Man, remember when you could go through an entire slideshow of big-name people at the Oscars and only have ONE slice of pizza?

    Also, I’d somehow forgotten Bai Ling existed (I know – this means exile from Fug Nation, doesn’t it?). Huh.

    • Sally
      +8

      I was thinking that the other day – remember how often Bai Ling and Paris Hilton showed up on the site, along with Brittany Spears? We hardly ever see them now which bodes well for us re:Kardashians. But that brings up the question of who will be our nails-on-a-blackboard person in 10 years?

      • Nora
        +10

        Speaking of former GFY frequent fliers, whatever became of the Peldons?

        • Krissie
          +5

          Oh my God, the Peldons. I loved the Peldons. Especially Courtney. Remember when she was engaged to Crispin Glover for about ten seconds? My favourite caption on this site was “Our pointless queen: Courtney Peldon.”

          I really think both Peldons have given up acting. There’s no other excuse for the fact we haven’t seen a picture of either since about 2008. I’ve never even seen them at, like, Z list events in “Us Weekly” with people like Audrina Patridge and Omarosa.

          • Jessica
            +1

            One of them is a casting director now. I think they’re both working behind the scenes.

            •  Nora
              +2

              Who could have imagined the Peldons of yesteryear being content to work (!) behind the scenes (!!!)? Maybe there’s hope for some of the Jenndashians after all.

  4.  mirna
    +2

    L

    •  mirna
      +11

      (oops, pressed enter by accident)

      La Kruger…that face! My god. S

  5. welshforjohn
    +31

    I actually REALLY like Reese’s gown. It looks like something Grace Kelly or Audrey Hepburn would wear. It’s sophisticated and classically pretty, and one of the best gowns she’s ever worn, I’d venture to guess.

    I see that Jennifer Aniston only wore black back then too. Some things never change.

    • filmcricket
      +6

      We’re getting to the point where I remember some of these dresses from the Wayback Machine, and I remember how disappointed GFY was in Aniston’s dress back then, too. It was her first Oscars since the split, and she had the opportunity to come out both barrels blazing and looking super-fine, and instead: THUD. A boring black dress, the same hair she’s had for 20 years, and a necklace that could have been spectacular had it not been fighting with the neckline of the gown. Such a wasted opportunity.

    • Roz
      +2

      Agreed! I think it’s adorable and so pretty and I really can’t stand her.

    • Bucky
      +4

      i actually liked Aniston’s gown. Even though it was black, again, and she did the straight hair down, again, the styling was different. I liked that it wasn’t another damn fitted black strapless column or some such, it was slouchy and a little flappery and I LOVED that necklace. If only she would wear color.

    • Emily
      +17

      Reese’s dress looks classic because it is. It’s a 1955 Christian Dior.

  6.  kissmyang
    +3

    OH Bai Ling…she might be wearing a gift bag but she is clothed in said gift bag. I cannot see any part of her hip bone…amazing.
    xoxo

    • Art Eclectic
      +21

      Really. When you think about it, Bai Ling IS a gift bag. A gift bag of crazy that any of us will accept at any time.

      I miss that gift.

  7. Chelsea
    +37

    Michelle’s look is my all time favorite red carpet look. She was so beautiful and is glowing. And, yes, I do think the tragedy that would befall them helps keep it so iconic. It almost hurts to look at, even though I love it and loved that couple so very much. Oh, Heath. :(

  8.  Caitlin
    +51

    Man, that dress on JLo. Why can’t she just do that over and over??

    • lilywise
      +21

      JLo could totally embody the sexy glamour of Sophia Loren from that period. I’d love to see her go more sexy by way of beauty and elegance than sexy by way of sheer and try-hard.

  9. Lizzy
    +27

    Love JLo’s green dress!
    Sandy and Keanu – sigh!

  10.  BeautyMarks
    +11

    Who’d have picked Meryl as the runner-up to Michelle Williams? It’s those two, and maybe JLo, and then you can dismiss the rest.

    • welshforjohn
      +14

      I would’ve picked Reese, actually, because I love vintage Dior, but Meryl and JLo looked good too. Nothing is better than vintage Dior or Givenchy to me though.

      •  BeautyMarks
        0

        I like Reese’s dress, but don’t care for the color on her at all.

        • welshforjohn
          +13

          I can see that. It would look better on someone with tanner or darker skin, like Penelope Cruz.

          I also like Keira Knightley’s gown, minus the mermaid hem. I love the color though and I think it looks spectacular on her.

    • Lizzy
      +4

      Yes, Meryl’s dress is divine. Reese’s is, too. Ah, for the pre-pizza dress days….

  11. Gina
    +21

    Thank you, Fug Girls. I am getting closer to 60 than I’d like, and sometimes I think, ‘hey, just pick a signature, plain look like Steve Jobs did, and forget fashion.’ And sometimes it’s ‘hey, how cool would it be to become eccentric? Wear weird stuff and don’t care what people think!’ Then you sent me Lauren Hutton and I’m all, ‘girl, get yourself into the bathroom and put on some makeup and a pretty dress!’

    • CassandraMortmain
      +13

      Yeah, what’s on her feet? Although I completely feel you on the rest of your comment. I’m your age and full on eccentric looks way easier with every passing year.

    • Deborah
      +3

      Hahaha, I feel you (nearing 60 myself). But having grown into fashion sense with La Hutton as my spirit animal, I can give her all the passes on dressing wacky now because, damn, that woman was sizzling hot all her life. There are a few iconic images of her I will always have in my mind: the jersy halter dress, the tuxedo, any number of white suits, the oversized white shirt. Love her, always.

    • greatwhitenorthchick
      +4

      LOL. Close to 60 over here, too. There’s eccentric and then there’s the I-got-dressed-in-the-dark fashion sense. Hutton has no excuse!

      Me, I love Mirren’s fashion sense. Can’t quite pull that off, though. A female version of the Jobs uniform works for me!

  12.  Ellen
    +34

    Now I understand why everyone raves about Kruger-she looked gorgeous here. And that body language in the link to the DMIK-painful. It literally looks like she’s hanging onto him and he’s having no part of it at all.

    • Emster
      +7

      Thing is, I think they’re turning a corner. Have you ever successfully turned a corner holding someone’s hand? You always either drift apart or crash into each other in an embarrassing way.

      Or maybe I’m being naive.

      •  Allison
        +47

        Ha, when I read your first sentence I thought you meant turning a corner metaphorically, like re: their relationship/potential breakup. Then your second sentence I was like, hmmm I think hand holding would aid in repairing a wounded relationship…

        Then I figured out you meant literal hand holding. DOH.

      •  Amy the 2nd
        +5

        I dunno – that looks like a man that doesn’t want to be held onto….

  13.  Sennalina
    +11

    This is excellent! As well as the main gowns I’m loving perusing all the people in the backgrounds – fugs and fabs all over.
    Also, the bodice of Amy Adams’ dress looks like a lobster wearing boxing gloves.

    • welshforjohn
      +13

      Yes, I hate Amy Adams’ dress. I think the bodice is horrible.

      • Shannon
        +8

        I remember Amy’s dress, and time has not improved my opinion. I thought it looked like a little baby corset was sewn on the front. It’s just about the dumbest thing I’ve ever seen.

    • Sally
      0

      I would have sworn Amy Adams was Debra Messing.

      • sarah
        0

        I think I’d actually really like Amy Adams’ dress if it fit–but boy is that fit terrible, especially in the bust area.

  14. filmcricket
    +31

    Wow, the mid-2000s was clearly Peak Spray Tan. JLo looks orange. The Krugs looks lobster-like. Charlize isn’t as Oompa Loompa-ish as she would be when she won for “Monster” but she’s definitely laid on the bronzer too. Thank goodness for Rachel Weisz, Anne Hathaway, Christina Hendricks, and other pale ladies who taught us it’s okay to be Ivory Snow, especially when the alternative is Tropicana.

  15. A.J.
    +25

    Diane Kruger is one of those celebrities that I can’t figure out why she’s a thing – like I can’t name a film project she’s been in. Who are you and why am I looking at you? See also, Camilla Belle.

    Seeing Bai Ling reminds me – my ex told me that he was at a thing recently and Bai Ling hit on him. I don’t know if I should be alarmed that Bai Ling and I had the same taste in guys?

    • welshforjohn
      +16

      She was in Inglorious Bastards. That’s all I can name.

      • Lauren
        +18

        Let’s not forget the cinematic masterpieces that were National Treasure, National Treasure 2 and Troy…

        • welshforjohn
          +5

          Lol I didn’t even remember that she was in National Treasure. I completely wiped that movie from my brain. I finally saw Monuments Men a few weeks ago and was really disappointed in it as somebody who went to school for art history and arts management (I thought it was REALLY hokey), and when it was over, I exclaimed, “This was like an art history version of National Treasure!”

          •  Allison
            +2

            I really enjoyed the book and literally couldn’t even finish the movie I was so bored.

            • welshforjohn
              +1

              I need to read the book. Watch the documentary The Rape of Europa for a much better and more informative film on the same subject matter. It’s a lot more interesting and riveting too, which you should never have to say when comparing a Hollywood movie to a documentary.

        • Amelia
          +3

          TROY!!!! Oh, man. I was also in college and studying Latin at the time, which only contributed to my sense of how epically bad it was (pun not intended…well…not at first). My friends and I even had a drinking game for the movie that my liver would likely not survive if I tried to play it again. I do remember that, bizarrely, some critics were making snide comments about how Diane Kruger was not attractive enough to play Helen??!! I mean….I don’t think that movie was ANY of the actors’ finest work, by a long shot. But any comments that she was somehow not beautiful enough to be Helen were as bizarre to me 10 years ago as they are to me now.

      • jeansheridan
        0

        And she was darn good in it. I think she’s done work in Germany too. She needs good material however. She can’t elevate crap like Cate Blanchet or Kate Winslett.

    • kay
      +5

      She starred in the bridge while it was on the air and she does quite a few foreign language films. Also national treasure, which is a guilty pleasure. I saw her in the French film about marie antionette, she was alright. She’s also big in the fashion world which is why she gets paid to turn up to places

      Now Camilla belle I can’t help you with. I think she was in when a stranger calls

      • Shannon
        +4

        Thanks for your original musings, A.J. as this is a topic that has puzzled me for a long time. If not for GFY, I’m sure I wouldn’t have ever heard of her. A few months ago, I think it was when we were discussing a pair of pink pants and the potential sheerness thereof, I finally had to look up her IMDB page and see what in the heck she’s been up to in her life besides wearing regrettable clothing. (I’m not at all sold on The Krug and her status as Fashion Icon either.) I was surprised it was so sparse.

    • Roz
      0

      Not to mention Rita Ora, Kaley Cuoco, Bella Thorne. Still don’t really know what any of them do.

      • welshforjohn
        +11

        Kaley Cuoco is one of the main stars on the hugely successful (and funny, imo) sitcom The Big Bang Theory, so she has a legit career.

      •  Annie E
        +8

        Kaley Cuoco is a star of one of the highest if not the highest-rated sitcom on TV right now, so… now you know.

      • charmedjenny
        +7

        Kaley Cuoco will forever be the one who ruined Charmed. God, she was AWFUL on that show.

      •  niksmit
        +4

        Rita Ora is a good singer who has yet to record a great song or get a great marketing team behind her. I first learned of her here and was shocked to find her singing well while flipping channels on the TV a couple years back. I had just assumed she was into attention-grabbing fashions because she didn’t have attention-grabbing talent.

        • welshforjohn
          +4

          She and/or her team tried to make her Britain’s version of Rihanna. Problem is, her songs aren’t as good as Rihanna’s, her style comes off as a poor man’s version of Rihanna’s style and the world already has Rihanna, so why did they think we want another one?

    • Kiti
      +6

      Diane Kruger was AWFUL in “Troy”. One issue, among many, was that she was horribly miscast. That whole movie was such a travesty.

      I never before realized that I have such strong opinions about “Troy”.

      • Michelle
        +7

        As a classics major, “Troy” broke my brain. When Menelaos died, I threw my hands up in the theater and yelled “WE ARE DONE HERE.” My boyfriend at the time quieted me down but it was excruciating to sit through.

        • Woosterphile
          +4

          Hello new best friend! I have Thoughts on that damn movie! I believe my exact words at his death were “and who’s going to give Odysseus the post war recap now?!” (I didn’t want a sequel but that’s never stopped Hollywood before.) Menelaus dead, Paris alive, that damn jump Achilles kept doing. I’ll stop because I’m making myself mad all over again lol

          •  roser
            +4

            Hated every bit of it except for Sean Bean as Odysseus. Now, that is a man…

        • Kiti 
          +2

          I had a Classics emphasis in my masters degree. “Troy” was the worst.

      • Amelia
        +4

        I commented on how hilariously terrible I found this movie before seeing this thread (and was getting an undergrad degree in classics at the time this came out). But I think Diane Kruger was the least of that movie’s issues. Her whole role was really just to sit there and look pretty and vaguely distraught about everything going on around her. I’m not sure how much more any actress could have done with so little.

        Brad Pitt, however, just completely — and kind of hilariously, in retrospect — clearly did not give a crap. He hammed it up SO MUCH as Achilles, but the writing was just so bad I think it was probably the best way for him to go and emerge with his dignity/career intact. Then everyone forgot about it almost immediately when Mr. and Ms. Smith and the whole Jen v. Angelina drama all followed on the heel of his Achilles performance (again, pun not intended….AT FIRST).

        I might have been more irritated by the movie’s inaccuracies in college, but the movie was just SO universally panned as soon as it came out, for reasons that had nothing to do with either historical accuracy or literary faithfulness to the Iliad, that I have a hard time even getting that exercised about it now. I know people who studied classics were mad at how inaccurate it was. Plainly some still are, and I love that. But I could never get that worked up about it, because my sense at the time was that NO ONE was taking it seriously at all to begin with because it just wasn’t good as a movie — unlike, to give another example that was very much of the early ’00s, Americans who read The Da Vinci Code and thereafter became convinced that everything Dan Brown had to say about art and history and religion was 100 percent grounded in reality.

  16.  Noodle
    +25

    Thank you for reminding me that I am equally invested in Sandra and Keanu’s genuine BFF status as I am in Kate and Leo’s. Love them!

  17. GrandSophy
    +14

    I know its a black dress- but there is something very lovely about Jennifer Aniston in that particular black gown – its very romantic and not her usual body con aesthetic.

    • Art Eclectic
      +5

      Aniston had yet to develop the official Aniston Costume, from which she would rarely deviate.

    •  Sonia
      +6

      I agree – Jennifer Aniston’s dress has a vintage look to it, very pretty neckline and beautiful flowy skirt, that I just love. One of my favorites from that year.

      •  Allison
        +1

        Agreed, ten years on I look at it and see general Aniston-ness, but at the time I remember thinking she looked great – very elegant.

    •  suzannadanna
      0

      Maybe it’s my monitor, but to me that dress reads dark (very dark) green.

  18. Andrea
    +10

    Regarding those Daily Mail photos of Diane and Pacey: The red building behind them is 12th Street Ale House, where Diane was allegedly caught smooching Norman Reedus. Granted, the bar is right around the corner from their apartment, so it’s natural they would walk by it a lot, but that’s an unfortunate backdrop to these “We’re still a couple!” photos!

  19. crookedE
    +9

    Kind of funny how Stephanie Seymour’s dress looks like a nun’s habit in retrospect, after the eyeball assault of sheerness we have endured lo these last 10 years.

  20. Julie
    +4

    Heather, I KNOW you chose this year so we could all sigh over that yellow dress/red lipstick combo again :)

  21. Megs
    +2

    everything looks cheap and the shoes are horrible. that is all.

  22. Mouse
    +28

    “This Wang is not as triumphant for me as Michelle’s.”

    *snicker* I have the sense of humour of a 12 year old.

  23. kay
    +14

    So many parts of this post hurt me.
    A) I miss heath ledger
    B) I loved and still love Reese Witherspoon’s dress and
    C) I refuse to believe pacey and Diane Kruger are broken up until they announce it. Also, body language? Really? And from the daily mail as well? Come on. These are the kind of papers who show a star frowning and decide she’s depressed. Can’t tell anything from a photo

  24. Jennifer
    +2

    Can we do one where you go back further than 10 years? The older the better!

    • welshforjohn
      +3

      Yes, like lets go back 50 or 60 years to 1956 or 1966. I bet many of the gowns would be divine.

    • Jessica
      +3

      It’s difficult to expansively source photos for very old Oscars ceremonies because the red carpet as we know it didn’t really exist back in the day.

      • welshforjohn
        +1

        That’s true. They still got all dressed up and decked out for the Oscars though, right?

        • Jessica
          +3

          Oh, sure. It’s just a different set up. (Those snaps are also, not for nothing, often extremely expensive.)

    • Mrs. Helpful
      +1

      People.com has a slideshow up right now with some older Oscars pictures from a range of decades. They are all black and white.

      • greatwhitenorthchick
        +3

        I saw a b&w pic of Audrey Hepburn when she won for “Roman Holiday”, and, OMG, what is going ON with her eyebrows. Seriously, it was a little scary.

        • welshforjohn
          0

          They were very sculpted, and in a bit of a weird shape too, but I don’t mind the look all that much. I like thicker eyebrows though, as long as they’re not caterpillars or a unibrow. I think Lily Collins has amazing eyebrows.

        • Mrs. Helpful
          0

          yeah, those were some crazy thick squared-off eyebrows!

    • Steph D
      +2

      Yes, this was SO FUN!

  25. Art Eclectic
    +33

    Salma Hayek used to dress SO MUCH better when she was a bombshell instead of the president of the PTA.

  26. Betsy
    +8

    I remember this Oscars so clearly. That Michelle Williams look might be my favorite Oscars look ever. This was the only year that I actually watched all the best picture nominees and many of the other nominated films (thanks to a great independent theater where I lived that served wine and netflix) so I was so happy to have real opinions. And I was NOT happy Crash won. I think it was my least favorite of all 5 best picture nominees. Ah, memories. I was such a baby back then.

    • Emster
      +4

      I remember It’s Hard Out There for a Pimp winning Original Song so vividly. Over Dolly Parton (not that I was all that invested in that particular track). I would also like to start a discussion about Taraji’s frosted eye shadow.

      •  Allison
        +11

        My favorite thing about Three Six Mafia winning was that in the next couple of years they would pop up on random VH1 shows like I Love the 90s or whatever giving little comments, and all of them were just casually holding their Oscars. As someone who might do the same if awarded an Oscar, it always cracked me up.

        •  Steph
          +7

          This was the year John Stewart hosted, and I remember him ad-libbing right after their win with, “Three Six Mafia – 1. Martin Scorsese – 0.” It was hilarious.

    • notemily
      0

      I’m still angry about Crash. Three Six Mafia winning was great, though, especially since Ludacris got to introduce their performance, and Jon Stewart got to make a Ludacris joke.

  27. welshforjohn
    +16

    Can we talk about how bad that hair is on Charlize? It’s worse than the overwrought satin gown.

    • Shannon
      +6

      There are a few people with not great hair here. Can we also talk about Jessica Alba’s hair, and how I had to stare at her for a long time to make sure she wasn’t wearing a giant Edwardian bun? There’s a guy standing behind her with poofy hair in nearly the same shade. I was funny once I realized what was really going on, but for a second there…

    • Ms Poopy von Pants
      +7

      It’s TERRIBLE! She looks like Ivana Trump in the 80s here.

    • sarah
      +1

      The hair (and that dress) are so aging on Charlize that I actually think she looks significantly older in that picture than she looks now ten years later.

  28. kmo
    +14

    I remember distinctly loving Michelle Williams’ whole look at the time – gorgeous and unusual dress and color, perfect red lipstick, beautiful hair and unbelievable skin. This is definitely up there with one of the all time best Oscar looks. (And Meryl Streep looks fantastic as well!)

  29. Livvie93
    +15

    Michelle Williams yellow dress might be the best anyone has ever looked at the Oscars. That picture makes me sad, too.

    • Teri
      +7

      That is exactly what I was going to say. It is literally the best Oscars dress of all times. She somehow looks elegant, beautiful, fun, effortless and natural all at the same time. And it makes me sad, too!

  30. Lynne
    +5

    I kind of love that Lauren Hutton showed up to the VF party as though she were meeting friends for a bottle of wine at the Italian joint on the corner. I bet she was the most fun person at that party.

    • Shannon
      +12

      It looks like she’s meeting a shaman for a session of peyote in a teepee. Still, it’s a look I treasure.

  31.  currygirl
    +9

    Oh man, Michelle William’s dress and Keira plum dress with that amazing necklace are so so so good! I think they’re both in my all time favorite Oscars dresses. I liked Keira’s whole look because sometimes her makeup isn’t great, but she really got everything right for this award show.
    And jeez, can we somehow get JLo to dress like that again? That was so interesting (I remember some caftan/sari-ish dress she wore too that was amazing!). Jennifer Aniston has been boring for so long, poor thing.

  32.  Calla
    +2

    At first glance, I fully mistook Keira Knightley for Isla Fisher. Weird, right?

    Also, I hadn’t realized that Jada has looked that fit for that long. Well played, Mrs. Pinkett-Smith.

    • kairu
      +4

      Jada Pinkett Smith has ALWAYS had an amazing body. There was one Oscars – late 90s, maybe? – where she wore a metallic green Versace. It was originally a gown, but her stylist said that her body was so great they decided to CUT OUT THE MIDDLE and turn it into a crop top and a skirt.

  33. Kristabelle
    +13

    That beautiful blue dress on Salma! AH! Her boobs are where they are supposed to be and she looks so beautiful!

  34. Elizabeth
    0

    The explosion on Naomi Watts is Christian Lacroix.

    • Kate
      +23

      I always chuckle when I read or hear the name Lacroix. It reminds me of Ab Fab. “It’s Lacroix, sweetie. Lacroix.”

      •  KarenG958
        +10

        Me too! I cannot hear the name Lacroix without hearing Eddie saying it.

      • Kiti
        +7

        I’m so glad that I’m not the only one to associate Lacroix with Ab Fab.

  35. J.Mo.
    0

    I thought Felicity Huffman was Jane Fonda, and Heath Ledger looks a bit like James Franco in that picture. Michelle Williams is gorgeous and I agree, it’s likely the best she’s ever looked.

  36.  kat
    +17

    That’s a depressing flashback when it comes to romance and love.

    • Shannon
      +11

      RIGHT? This is like a divorce parade. I didn’t realize how many people had broken up? Nice to see William H. Macy and Felicity are still plugging along and though not pictured together, Will and Jada were nearly 10 years into their marriage at this point.

      • Shannon
        +6

        It’s sad that I just looked this up. Yes, this is what I’m doing with my Friday morning:
        -Nicole Kidman would marry Keith Urban in June of 2006 and they still seem to be coupling along.
        -Naomi Watts and Liev Schreiber were together, and still are.
        -Sienna Miller and Jude Law were still together, but that one went south.
        -Of course, La Streep was married and still is.

  37.  Iolanthe
    +11

    Did you say Charlize Theron’s dress was “hand-painted”? It’s black! What’s even the point of that?

  38. J.Mo.
    0

    Oh, and Stephanie Seymour – if you are going to wear a shear bottom then please tan yourself all the way up to your knickers. No one wants to see a bikini tan line through said sheer.

  39. Patrick
    +12

    I look forward to the 2007 flashback when Reese was on her Divorce Tour. Everything about her look that year was amazing. HAIR. DRESS. ATTITUDE.

  40. Kate
    0

    That Michelle Williams look is still one of my all-time favorites. I love these sorts of retrospectives. I remember thinking that a lot of these people looked great at the time, but now I see the photos and cringe.

  41.  Katie
    +4

    I’m still laughing about the “magic mailbox” Halloween costume.

    • jeansheridan
      0

      And how did he explain it since that movie wasn’t exactly a “hit”. Keanu and Sandy …physically they’re meant for each other. All that dark hair and good cheekbones. Sigh. Keanu never went blond for anything, did he? I hope not.

  42.  Prinzessin
    +33

    When Oscar photos show more than celebrities and clothes:

    I have the honour of knowing some people in the background. In fact, a very close friend was able to attend the Oscars annually and she often popped up in the background of these photos. Unfortunately, she passed away due to brain cancer a few years ago but these lovely images help keep her memory very much alive. Thank you for posting.

  43. Kirsten
    +1

    I don’t care about Reese Witherspoon’s dress, but I’d like to know more about the blue one behind her.

  44. Jenz
    +3

    Hilary Swank’s ‘peaks’ (ahem) nearly made an arrival in that dress. HOIK, Swank! HOIK!

    Love this recap!!

    •  DianeN
      +6

      “Hoik, Swank, hoik” sounds like something you’d hear on a Viking ship!

  45. Caroline
    +1

    Good lord Charlize Theron is top to toe extreme 80s. The dress! The hair!

    Love these flashbacks btw.

  46.  Sarah
    +2

    Michelle William’s yellow dress look is SO good. Best she’s ever looked for sure.

    Sienna Miller looks like she’s dressed for a ladies lunch or something much less formal than a red carpet.

    Is Terrance Howard carrying a purse? Weird.

  47. Emily
    +3

    I’m in the very tiny minority here, but I never liked the dress Michelle Williams wore. And with the red lipstick it just looked too ketchup and mustard.

    • filmcricket
      +1

      I actually agree on the lipstick; she needed to go with a bluer red, rather than an orange-y one, for that exact condiment-based reason. I like the dress, though.

      • welshforjohn
        0

        THIS! Thanks for explaining why I don’t like that shade of red with the dress! It’s too orange-y a red! You’re right that she needed to go with a bluer red.

  48. Kathy
    +5

    When you mentioned the 2006 Oscars, my first thought was “Ah yes, those were the days when I was mentally planning my wedding to Joaquin Phoenix, oblivious to any forthcoming mockumentary shenanigans.”

  49.  Carla in Kentucky
    +7

    I want Keira’s necklace.

  50. Stacey
    +16

    I must admit- Michelle Williams is one of my favorite Oscar dresses of all. When I got married a few months ago, I was asked what I want my wedding dress to look like…my response, “I want to look like Michelle Williams from the 2006 Oscars”. With a few minor changes…I got my wish and couldn’t have been happier.

  51. Kiti
    +3

    I have So Many Thoughts.
    Slide 1 – “North Country” is one of those terrible, self-important movies, full of people dirtying themselves up as Oscar bait. Charlize Theron isn’t that good, but she isn’t any worse than anyone else in it. I just imagine everyone on the set telling each other, “This is GRITTY and BLUE COLLAR. We’re addressing IMPORTANT ISSUES.” Anyway, even Charlize Theron cannot carry off this monstrous dress. And what is up with that hair?
    Slide 2 – The dress is fine (I don’t hate it, nor do I love it as much as everyone else apparently does), but her undone hair has always bothered me.
    Slide 3 – I actually love this dress, but think Reese needed much better styling and makeup to really pop. It could have been great, but it was a missed opportunity: nothing about this look says “Winning an Oscar tonight!”
    Slide 6 – I remember making the comment that this Oscars was the year of people wearing vegetable colors: Michelle Williams in squash, Jennifer Lopez in asparagus, Keira Knightley in eggplant. Jennifer Lopez looks great, happy, and alive. The silhouette is flattering. Jewelry, bag, and shoes are fantastic… I can’t believe this is the same person as the dead-eyed, flesh-flashing Jennifer Lopez of today.
    Slide 9 – This is… not good. I wanted so much better for Amy Adams.
    Slide 11 – Maggie Gyllenhaal is wearing a maxi-length beach cover-up from Anthropologie. Without a bathing suit underneath. However, I am loving 1994 Goth Lady right behind Maggie.
    Slide 13 – Do you remember when Sienna Miller kept using that neckline with different dresses? DO YOU? I can’t find it in the GFY archives, but I distinctly remember that she had that same crazy studded leather neckline/collar with a short dress worn during this same 2005/2006 time period.
    Slide 19 – I am 95% sure that I tried on this very dress in a Southern California Windsor store in spring of 2006!!
    Slide 21 – I actually think this looks awful, but Meryl Streep has showed up looking worse, and meh, she’s Meryl Streep. Whatever. I might like it better if it was just less depressing, because this color scheme here evokes both mold and mud. To unfug it up, make it midnight blue (the flowers could be lighter blue, or white, or varying shades of yellow), and add a necklace and bracelet(s)? Yes, improvement.
    Slide 23 – Sure, Terrence Howard looks fab, but who is that white-tuxedo-clad cutie behind him?!
    Slide 27 – I need a dress in that color. Not that particular dress, just that color.
    Slide 28 – Sartorial madness, but dang if that particular shade of blue isn’t great on HBC.
    Slide 31 – Money can’t buy good taste. Or: You don’t have to be poor to be white trash.
    Slide 32 – I love this, but it didn’t quite make it to a homerun. Bai is working it, and the dress is very “Poiret 1910s” (love it!). She just needs a better hairstyle and a deep red lip.
    Slide 33 – PIZZA. LEOPARD PIZZA. Stephanie Seymour commits high crimes against humanity and her own genetics. In other news, maybe I’ll get some pizza for tonight – it’s Friday, after all.
    Slide 34 – Lauren Hutton’s shoes almost match the Vanity Fair logo next to her feet. That’s all I got, folks.

  52.  Patty
    0

    I loved the idea of Reese’s dress, just not on her. It needed someone taller (which, as a petite woman, it pains me to admit) and more glamorous. I think I recall chatter at the time that Nicole was in the midst of planning her wedding and maybe her Oscar gown was one of the reject designs. Michelle Williams is perfection. I so wanted Heath to win for “Brokeback Mountain.”

  53. Aria
    +1

    Michelle Williams’ gown is one of my all-time favorites…just perfection. And I loved them as a couple…. I’m kinda with the others that say this slide makes them sad.

  54. Whippers
    0

    I’m pretty sure Heather loved Jessica Alba’s look back in 2006. Remember that very specifically.

  55. sophia
    +4

    I already love Heather and Jessica but the #Hamildis has taken that love to NEW HEIGHTS. I’m immediately incorporating into my insult arsenal.

    Also, I cannot WAIT for fug madness to start, it’s my favorite time of the year. bless you for performing this public service.

    • S in Seattle
      +1

      That line cracks me up every time I hear it (which was last about 40 minutes ago, as we are listening to the soundtrack on a car trip.)

  56. Cristina
    +1

    10 years later and Michelle Williams Oscars look is still one of my all times favorites. OMG! That dress, the color, her hair and make-up and damn that necklace, so fucking gorgeous. Perfection, perfection, perfection.

    My heart still aches every time that I see a photo of Heath Ledger. Man, you were gone to soon.

  57.  Cas
    +1

    Look at Noah Baumbach! Look at that try hard model-y face he’s making! Look at his hair, falling in his face just so! You know he’s probably very serious (and most likely humorless) in person, and yet all that pretentious gas evaporates when walking the red carpet. Even Noah Baumbach is not immune to the try hard. This is comforting!

  58. Krissie
    0

    These retrospectives are so fun! I love them! As for the actual dresses, I know it’s crazy but I kinda like Charlize’s dress, it’s a beautiful colour, and she is wearing gorgeous shoes. Reese looks like she’s going to a wedding in the 1950s. Jennifer Aniston has the most boring black dress and basic hair in the room, as usual. I can’t believe how boring she always looks when she has access to the most amazing fashion and hairstylists. Michelle Williams’ dress… I dunno. I think it’s overhyped. Great colour, but the dress itself is meh to me. Jessica Alba’s dress is great but I absolutely hate her hair, it looks like how an old lady would wear her hair to a party. Jen Lopez, I think that dress was the best she’s ever worn. Such an improvement over her usual trashy “Look at my boobs hanging out! Look at my ass hanging out!” dresses.

  59. jaime
    +1

    I have always hated Michelle Williams’ dress, actually. Love her, hated this dress. I know the rest of the planet feels differently. It’s just pure fug to me – weird color, strange bodice, meh.

  60. Kate on the Domestic
    0

    I think the 2006 Oscars may have been a high point for me. Both Michelle’s and Keira’s dress linger in my memory as top favorite Oscar looks.

  61. Kate
    0

    Umm… I wore that dress Salma Hayek is wearing in slide 18 to my school leavers’ ball!! It’s literally the exact same dress and I had no idea until that slide popped up

  62. MrsThurstonHowell3rd
    +2

    There is an Angel Sent Down from Heaven behind Terrence Howard, ready to bestow The Fug Girls with a pink rose in honor of their efforts to save us all from the Canto of Sins Against Sartori.

    This retrospective makes me realize that “for ten years we’ve NOT been on our own”.