Oscar Style Retrospective: My favorite gowns of the last ten years

I keep noticing various sites are running Oscar fashion retrospectives, so I thought we should try it too! And yes, it’s really slow today. The dresses I’ve chosen to profile aren’t my picks for “Best Oscar dresses ever!” Nor are they my choices for “Best Dresses of the last 20 years or so.” Our photo agencies have archives, sure, but there are limits, and those limits seem to be “The Year 2000.” So these are some of my favorite dresses of the past dozen years (or so). Retrospect is a powerful thing – some of these dresses didn’t blow me away when I actually saw them for the first time, but I admire the choices more and more over the years, as I see that some of them were prescient, ahead-of-the curve, harbingers of styles to come.

Some of my picks might seem like I’m trying to avoid “the obvious gowns” – which is true. I truly hate some of the “popular” gowns – like Sandra Bullock’s hideous Marchesa in 2010, or Michelle Williams’ mustard Vera Wang in 2006 (it was an unflattering color, and an unflattering cut). Which brings me to another point – I’m not opposed to doing a “Most Hideous dresses of the last dozen years” post, so we’ll see how this one turns out. Let’s begin!

Angelina Jolie in 2004 & 2009. Angelina in 2004 was maybe the best she’s ever looked. She’d just filmed Alexander, and she was strong from training for Mr. and Mrs. Smith. Her body looked gorgeous, and the white dress was just perfect on her. At the time, I hated the overdone necklace, but in retrospect… it worked. It totally worked. As for her black gown in 2009 – I liked the simplicity of it. It was tailored beautifully, and she kept her jewelry stunningly simple with those emeralds.

Angelina Jolie in Elie Saab, 2009

Angelina Jolie in Marc Bouwer, 2004.

This Renee Zellewger choice is not my first one – I loved that yellow vintage gown she wore, but this one is a good choice too. Renee was filming the second Bridget Jones movie, so she was carrying some extra weight, and it looked so, so good on her. Plus, this was the beginning of her long-time collaboration with Carolina Herrera, and that pairing is magic. I loved how classic she looks here – and she won too!

Renee Zellweger in Carolina Herrera, 2004

Nicole has so many strong Oscar moments, it’s hard to choose just a few. So I went for the more unconventional picks – her Gaultier in 2003, which is when she won for The Hours, and the Chanel in 2004. The Gaultier is great because Nicole used to love black so, so much, and it really was an unconventional choice for her, especially because she won. This is dark, goth Nicole that I miss. As for the Chanel – it was just exquisite. It was simply a gorgeous dress.

Nicole Kidman in Jean-Paul Gaultier, 2003

Nicole Kidman in Chanel, 2004

Like Kidman, Cate has so many great Oscar red carpet moments. These are just two of my favorites, although I really wish we had photos of her black Gaultier in 2000, which was so amazing. Here we have Cate’s Valentino – a fascinating combination of yellow and red, and Cate looking so glamorous and old-Hollywood. Also, her metallic Armani, which is even better years after the fact.

Cate Blanchett in Valentino, 2005

Cate Blanchett in Armani Prive, 2007

This is the one CB and I were debating – CB didn’t think Halle’s Elie Saab was anything great. I think it is – even more so in the history of Oscar fashion. I didn’t think much of it when I first saw it on the red carpet, and I couldn’t believe that she had chosen it. But then she got on stage when she won… and all of a sudden, I understood the dress. The dress looked PERFECT on the stage. Plus, I love that she wore a little-known designer (at the time) – Bradley Bayou.

Halle Berry in Elie Saab, 2002.

This is maybe my favorite thing that Kate Hudson has ever worn. I’m not a huge fan of hers, nor am I Hudson hater, but this fashion moment was timeless. I almost always hate blondes in these pale, beigey shades, but Kate had just the right amount of tan, the perfect makeup, the perfect hair and the perfect body for this gown. Instead of looking fussy, the beaded lace looks expensive and gorgeous.

Kate Hudson in Versace, 2003

I said I hated Michelle’s 2006 mustard gown that always makes everyone’s top ten. And here’s why – because she can pull off this kind of strong, glamorous, perfect look. This is how a movie star should look at the Oscars.

Michelle Williams in Chanel, 2011

Charlize is a red carpet all-star, and what she wears to the Oscars always manages to make headlines. I feel like Charlize, Nicole Kidman, and Penelope Cruz were in a style death-match for several years, each one trying to out-do each other for the “strongest” look. Charlize’s strength is that she can wear clothes that look like they came right off the runway – her looks is “editorial” as they say. Here’s Charlize bringing two HUGE style trends to the carpet. We’re still seeing variations on these gowns today.

Charlize Theron in Christian Dior, 2005

Charlize Theron in John Galliano for Christian Dior, 2006

Some people thought Penelope was copying Charlize’s look in 2007. But I don’t think so. I remember when I saw this for the first time, I wanted the gown to decide what it was – I wanted it to be all-fitted, or all-frou-frou. But in retrospect, Penelope looked amazing and everyone is still trying to copy her.

Penelope Cruz in Atelier Versace, 2007

This dress still holds up, and it will hold up for years to come. This is one of those moments, where a celebrity simply looked their absolute best. Nowadays we know Alba is miserable, but back then? She was the hottest thing, and she looked perfect on the red carpet.

Jessica Alba in Versace, 2006

Reese’s Nina Ricci is still a marvel of simplicity, smart design and minimalism. She was post-divorce, and she gave up the cotillion styles and this was the culmination. I’m still completely in love with this shade of purple too.

Reese Witherspoon in Nina Ricci by Olivier Theyskens, 2007

Here’s what I love about Oprah’s Oscar fashion: Oprah knows it’s a big deal. She gets a gown specially made. She goes on a diet. She wears huge diamonds. I also love that Oprah shows the world that you can be a “bigger” woman and still look gorgeous at the Oscars.

Oprah in Gianfranco Ferre, 2004.

Oprah in Vera Wang couture, 2005. Shown with Halle Berry in Atellier Versace.

Photo credit: WENN, Fame and PRPhotos.

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73 Responses to “Oscar Style Retrospective: My favorite gowns of the last ten years”

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  1. jamminatorr says:

    I want to be first on here to say this: if Rooney Mara actually wins that Oscar I will literally shit. Not in a good way. I can’t even believe that she was nominated.

  2. mln76 says:

    I love Angelina’s 2004 look (DUH) perfection.
    Nicoles 2003 dress is just beautiful. If only the woman would age naturally and had kept the freckles.
    Cate Blanchett is my be all end all favorite everything she’s just so great.

  3. Esmom says:

    Reese in the Nina Ricci is the best she’s ever looked. Oprah in the gray is beautiful, too.

  4. k says:

    I hate most of these dresses. To each her own.

  5. Dorothy#1 says:

    That Hallie Berry dress is my all time favorite dress!! I also really like Cate Blanchet’s yellow and maroon.

  6. DesertRose says:

    Angie in the white dress is insanity. I had forgotten all about that until I saw this pic. What a gorgeous women. Girl crush back in effect. lol

  7. Samigirl says:

    Kate Hudson’s Versace looks expensive because it WAS expensive. Actual 14K gold is in that gown! That and AJ’s black are my faves on this list. Both are incredibly lovely.

  8. Nev says:

    fun post…should do more like this for sure.

    nicole…great in black…the hours…fantastic.

    halle with oprah…amazingly beautiful.

  9. paola says:

    I really hated Halle Berry’s then and i hate it even more now! it looked like she had a towel wrapped around her hips and droopy breasts.. not my thing AT ALL

    • TG says:

      Agree. Everyone raved about Halle’s dress and I thought it looked cheap. It reminded me the appliqué clothes we used to make in 4-H growing up. Hideous. Now the pic of her with Oprah I love that dress.

      • paola says:

        i loved Angelina in total black with those stunning emeralds, her eyes popped out and she looked beautiful, but i hated the white dress on her, her breasts looked weird and the fabric looked so cheap and the hair was horrible. The best dress in my opinion were Kate Hudson’s and Reese’s. the nina ricci gown was stunning but her hair was messy and too simple but kate hudson wore the golden gown with attitude and plus she had that smile that is always a win for her. too cute she was!

    • Aqua says:

      Agree! didn’t see what the fuss was about then and I don’t see it now.

      • blouson says:

        I still hate HB’s burgandy cellophane hummingbird cr-ptastic dress. Gross! SO much better with Oprah.

        Cate Blanchett looked amazing in both of hers. And she could wear them today. I thought Jolie looked ugly in her white dress. I always thought she got a better stylist when she paired up with Brad. She grew her eyebrows back and started covering up more. It turned her from abit odd looking to beautiful. That and the skeletal frame. When she is not stick thin she looses her cheekbones and just looks moon faced. Not saying she should starve herself, just that regrettably she is one of those women who I think actulaly looks better half starved.

  10. original sandy says:

    love angelina’s taste, she is stunning, on the other hand, oprah? she looks great here, but, what happened to her today? nicole, penelope, charlize, halle,and cate b. looks really beautiful, they are beautiful women any way. angelina looks so much better since hooking up with brad.

  11. fd says:

    Love it, I think these are great choices!

  12. fancyamazon says:

    I have always loved the Chanel on Nicole in 2004. I also love the Ricci that Reese had in 2007.

  13. LAK says:

    I would have loved loved loved Penelope Cruz 2007, if only Elizabeth Hurley hadn’t worn the same dress [but with sleeves] for her wedding a few weeks before Penelope.

    Loved the Reece Witherspoon 2007

    I always love Cate at the Oscars but for me, her all time fav look is her first time at the oscars. 1998 in Black Galliano with multi coloured hummingbirds embroidered accross her back!

  14. toto says:

    i think Angelina has a problem… she has too attractive face that makes any dress she wears is no big deal or like a sack.

    she does over shadow her own style..
    i think one of the company she was modeling for said the same ..i guess they r right.

    • TG says:

      Interesting observation. . . but what a problem to have.

    • Jill says:

      Several film critics have said the same — that Jolie’s looks are so striking that when she plays a role, she overshadows the role. You don’t see the role she’s playing, you see her playing the role.

      That said, I love the white dress. I’m not altogether crazy about the black one, but OMG those emeralds!

      Cate Blanchett’s graphite colored dress was drop-dead gorgeous and she was wearing the hell out of it. I thought Michelle Williams’ dress was lovely but it needed some chandelier earrings, not those little studs.

      Halle Berry’s dress was a hot mess.

  15. Mafgee says:

    such boring taste you plain jane housewife.

  16. Agnes says:

    i loooove cate blanchett’s yellow gown. and have a huge soft spot for halle’s gown.

  17. alex says:

    Most of these are different versions of the same dress, but I see what ya like.

  18. Amanda G says:

    I guess we have completely different tastes because I think all of those dresses are ugly with the exception of Halle Berrys. The Oprah dresses you picked aren’t even her best. She always looks fab though and she should with the amount of money she has.

  19. Lem says:

    Hmm. Kate Hudson does look great, imo
    Meh. Worst dressed is much more fun. Let’s do that. We can relive Barbie Ballerina Bassinger!

  20. Lindsay says:

    Ooh, I love Cate Blanchett in anything. Lovely. Have to disagree about Michelle Williams though – I don’t think she ever looks good. :-/

  21. NM6804 says:

    - Blanchett, Kidman and Theron always bring it. I always look forward to their fashion choices.

    - Jolie looked out of this world, crazy gorgeous from 1999 – 2005. Her best years looks wise.

    That said, I don’t agree with many of the dresses but taste always differs. That’s what makes debating so much fun. Plus it’s hard to choose the best of the best when you got the Three in your list. You could do a separate post on them and still can’t cover their best choices!

  22. skuddles says:

    That weird, strappy crossover black number that Nicole is wearing simply confounds me, its horribleness cannot even be measured – worst dress ever!!

  23. Kate #2 says:

    I think Cate Blanchett’s embroidered hummingbird dress by Galliano in 1999 was really beautiful. Simple at the front, and that incredible mesh back. It flowed exquisitely when she moved, too, and it looked comfortable to wear as well. All round win.





  24. Jaxx says:

    Most Oscars gowns are forgettable to me but one I’ve never forgotten: Susan Sarandon won in 1996 for Dead Man Walking and she came in a big poofy copper confection that matched her adorably short copper curly do. When she walked onto the stage in that lighting she looked like a fairy godmother. She was so stunningly gorgeous I just gaped at her. I’ve looked back at the pictures and they don’t do justice to that moment in the right lighting when all that copper goodness just shimmered like a magical aura around her.

  25. Ashley says:

    PLEASE PLEASE PLEASE do the most hideous dresses!

  26. HoustonGrl says:

    Nicole’s JPG sleek black dress is one of my favorite dresses of all time. I think it embodies the essence of sexy and elegant – a tough combo to pull off. I’ve looked for something similar for years, but never found it (well, or maybe I just can’t find it in my price range).

    I LOVE Renee Zellwegger in that white dress and didn’t even remember her wearing that.

    Finally, Cate Blanchett in Valentino. Just wow. That dress is absolute perfection!

  27. Snowpea says:

    Errrr, how much HAS CHARLIZE CHANGED?

    That girl is virtually unrecognisable now!

  28. pandabear says:

    I love the wine colors of Halle’s dress but it seems a little bit slutty, eh?

  29. danielle says:

    Ooh, loved this post. Worst gowns now, please.

    • Jill says:

      A list of the worst dresses would be fun. My list off the top of my head:

      1) Bjork’s swan dress
      2) The purple horror on Zoe Saldana
      3) Cher wearing nothing but beads
      4) Paltrow’s Pepto Bismol pink prom dress
      5) That godawful purple/yellow thing Cate Blanchett wore last year that looked like a bad case of measles

  30. Aqua says:

    I love Angies Elie Saab dress simply because it fits her properly.Their is no gap between her chest and the dress that so many of todays dresses seem to have.

  31. Jackie says:

    good post!

    cate b in that yellow dress was stunning.

    nicole and chanel are a match made in heaven.

  32. foozy says:

    no no no!!! you missed out charlize’s dress at the oscars. the one that was light orangish in color. that was by farrrrrrr her most beautiful and glamorous look!!! she became more famous after that..

  33. blouson says:

    What about Kidman in that yellow/lime/chantreuse asian inspired sheath? THAT was the best Oscar dress ever…

  34. lucy2 says:

    I love both of Cate’s, and Kate Hudson’s.
    There have been a lot of gowns in the past ten years or so that I’ve liked a lot more, but I get that photo rights are limited. Anne Hathaway had a gorgeous one a few years ago.

  35. Gabrielle says:

    My favorite possibly ever was Reese’s black and white dress from last year. People said it was pageanty but I loved the 1960′s movie star Barbie look she achieved.

  36. Amy says:

    Whhaaa? I can’t believe I disagree with you on so many of these. I think the Nicole Kidman dresses are awful! Hated Halle’s dress then, and it hasn’t gotten more appealing with age. And Cate Blanchett has looked so much better than in these two gowns. Michelle Williams – no! Charlize Theron – seriously? Those are both laughably bad, and/or ill-fitting and/or dated looking.

    Of these, only Reese and Kate Hudson would make my list.

  37. Isa says:

    I love both of Cate’s dresses. The maroon and yellow, perfect.
    The grey dress looks like liquid metal! Amazing.
    I also love Kate’s dress. She pulls of small breasts so well, wish I could.
    Angelina’s white dress inspired my Junior prom dress. She looked so amazing there! Even after “bulking up” she still had thin arms.
    I can’t stand Michelle Williams.
    Jessica Alba’s dress was amazing and her body was perfect, but I hated the color of the dress. Was it supposed to be gold? Because it looks like a gross yellow.

  38. Paige says:

    has Jessica Alba had implants since then?

  39. Mara says:

    Cate Blanchet dresses are stunning she is so beautiful .

  40. Lisa B. says:

    My favorites
    Huge and picture heavy post!
    But hey, there’s no use without pics.

    - Gwyneth Paltrow
    2002, Alexander McQueen —> http://bit.ly/ynMERA
    2007, Zac Posen —> http://bit.ly/zmCxxc

    - Reese Witherspoon, 2002, Valentino — > http://bit.ly/xFTxlP

    - Halle Berry, 2002, Elie Saab —> http://bit.ly/AkRCpQ

    - Renee Zellweger, 2003, Carolina Herrera —> http://bit.ly/zf6kDr

    - Julianne Moore, YSL, 2003 —> http://bit.ly/wJmVc1

    - Charlize Theron, 2004, Gucci —> http://bit.ly/z6LJK3

    - Anne Hathaway, Marchesa, 2008 —> http://bit.ly/zl258c

    - Diane Kruger, Chanel, 2010 —> http://bit.ly/zCEubE

    - Rachel Weisz, 2007, Vera Wang —> http://bit.ly/zc5jCn

    There are many others, but I don’t want to get deleted by the spam filter, :(

  41. Annie says:

    Guess I have very different taste because I loathe all these dresses except the second Angelina Jolie one and the second Cate Blanchett one (Cate’s first dress would be nice too but I hate the color). Good grief what is that messy grey THING Kidman is wearing? Looks like she wrapped some old dishrags around herself. Kate Hudson’s, Jessica Alba’s, and Halle Berry’s all remind me too much of lingerie and Reese’s looks like seaweed.

  42. Jo 'Mama' Besser says:

    Yeah, worst.

    That thing with the bicycle shorts Demi Moore wore.

  43. Jin says:

    Charlize Theron’s best dress was the tangerine halter gown from 2000. That was one of the best Oscar looks ever.

  44. mek says:

    Does anyone else not get the fuss about Angelina Jolie’s black Elie Saab? People wear black strapless dresses all the time to the Oscars. Fashion commenters were raving about it as if it was the most incredible thing ever when she wore it. Annoying how people only started raving about Angelina’s fashion once she got with Brad Pitt. Before that, her fashion was judged as boring or weird.