Oscar Best Dressed: Sandra, Meryl, Penelope & that’s about it

82nd Annual Academy Awards - Arrivals

Just FYI, I’m going to do an epic Worst Dressed post later on, and it’s probably going to be crazy long just because of the Parade of Fug coming down the Oscar red carpet. It’s a little unbelievable how horrible the dresses were for the most part… but I digress. This post is for the best dressed, few and far between. So, let’s start with the newest queen/princess of Hollywood, Sandra Bullock (above). I loved this dress, mostly because Sandy was the one to wear it. It complimented her figure, it was a good (not great) color on her, and the detailing was especially pretty. It photographed well, which Sandy doesn’t always think about with her fashion. I think this was a big fashion win.

Now, I gasped when I saw Meryl. This is the kind of dress you wear when you’re the Grand Dame of Hollywood. She looked like a queen, she really did. Beautiful cut on the dress (designed by Project Runway alum Chris March, who also did her Golden Globes dress), and absolutely gorgeous styling – great hair, stellar makeup, and it was just the prettiest I’ve seen Meryl look in a long time.

82nd Annual Academy Awards Red Carpet Arrivals

Penelope Cruz got it right again! I have to admit, I hated her dress last year, when she won, it was much too princess-y. Penelope is at her best when she does glamour and goddess, which is what a blood-red strapless gown says to me. Love the neckline, great hair, great makeup, and the dress moved really, really well. One of my favorites.


I really liked Rachel McAdams’ dress, even though it was on the verge of pissing me off. It was too pale, and it looked dated to me, but even so, I ended up liking it because of the way Rachel pulled it off. I wish she would go darker overall, though. Darker hair, darked colors. But she looked nice.

82nd Annual Academy Awards - Arrivals

Kristen Stewart was a good example of a pale girl knowing well enough to go for a jewel tone that wouldn’t wash her out. I thought the dress itself was gorgeous, beautiful cut, the fit could have been a little better, but I suspect that had more to do with K-Stew’s bad posture. It could have made Kristen look too “old” but I liked how little she accessorized, and how simple her hair was. She’s becoming a little fashion maven, I’m so proud.

82nd Annual Academy Awards - Arrivals

I loved Cameron Diaz’s dress too, but did you notice how differently it photographed from the red carpet to the Oscar stage? I thought she had changed at first. On the red carpet it looked like a rich gold color, on stage it looked so much paler. But the dress had gorgeous detailing, and Camy was tan enough to pull it off without it washing her out.


I thought Best Director winner Kathryn Bigelow was one of the most elegant women there. And man, does she have a great figure or what? Seriously, this is one beautiful, classy woman. Great color, great fit, great styling. She looked prettier than most of the actresses there.

82nd Annual Academy Awards - Arrivals

I thought Queen Latifah looked gorgeous. But I adore whatever the Queen does. I especially liked the pale lilac color – it looked amazing with her skin tone.

82nd Annual Academy Awards - Arrivals

I hate to say it, but Demi Moore kind of pulled this off. Yes, in certain light the color washed her out, and yes, it was derivative of Penelope Cruz’s great Versace a few years ago, and yes, she needs to eat a cookie. But it worked.

82nd Annual Academy Awards Arrivals

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64 Responses to “Oscar Best Dressed: Sandra, Meryl, Penelope & that’s about it”

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  1. Ethel says:

    Was Jack Nicholson there? He’s always there in one of the front rows. I guess Robert Downey was taking his place sporting the cool shades.

  2. ruru says:

    Disagree with you on Demi Moore. The dress is nice, but I think she’s too skinny for her age.

    There weren’t many stand-out dresses this year! But strangely enough I can’t get over how amazing Sandra Bullock’s hair is.

  3. ruru says:

    Oh sorry, didn’t realise Kaiser had pointed out the fact that Demi was on the skinny side. I’m a bit buzzed.

  4. sickofit says:

    ah queen latifah she is so beautiful and that dress looks amazing. and of course meryl streep: gorgious. Did penelope cruz something to her face? her eyes look cat-ish…

  5. isabelle says:

    Cameron Diaz looks like a transvestite in that photo! Eek!

  6. mollyb says:

    I’m going to disagree on Penelope’s dress. It’s not that it wasn’t pretty–it was–it just feels like she’s worn a variation on that dress like a dozen times before. There was nothing new or interesting about it.

  7. mr. stinky fishface says:

    What about Deborah Ann Woll? She looked fantastic!!

  8. hmm says:

    Isn’t Cameron’s dress the same as one Taylor Swift had worn previously? The whole golden hair/golden dress thing…

  9. snowball says:

    I didn’t watch all of it, but there seemed to be three trends: sparkles, dresses with origami like folds and pleats all over and floaty chiffon ruffly things. Okay, four – this shorter in front, longer in back thing. Demi looked like a washed out can-can girl.

    Kate Winslet looked nice, if a little understated – what struck me was how much weight she seems to have lost.

  10. Linda says:

    Demi Moore – really?? – I hated the dress and her hair. Why was Demi even there – besides to present????

    Hated Kristen Stewart’s dress as well.

    Sorry – but I loved Sarah Jessica Parker’s entire look – it was vintage and a throw back – loved it! I also liked Carey Mulligan – but Lenny Kravitz’s daughter looked amazing – loved her dress and the color was amazing on her!

  11. Dorothy says:

    Meryl looked like a goddess! So beautiful !!!! Did not like Penelope, but I never do. I thought that Robert Downey’s wife looked great I loved her dress!! Also loved Queen she usually does her body justice!

  12. Jackson says:

    My top choices were Meryl and Queen Latifah. Meryl looked even better on video on the red carpet than the still pics. She looked ethereal. QL looked awesome – great color, great cut. Perfect.

    My second tier choices were Sandra and Penelope. Like Meryl, Sandra looked better on video than the still pics. Cameron Diaz did look good – better than I remember her looking in a long time. And Kathryn Bigelow – I’d wear that dress in a second.

  13. Chana says:

    Meryl, Queen Latifa: Gorge.

    Everyone else…eek.

    Penelope Cruz and Cameron Diaz have the unfortunate “boxy” figure. Drop waists and natural waists therefore make them look dumpy and square around the middle. The dresses were gorgeous but would have looked better had they either been on other, curvier women or they had worn better foundation garments.

    Speaking of foundation garments, poor Kathryn Bigelow. I was watching the Red Carpet and such on E! and when she popped up all I could see was her little tummy pooch and the fabric of that awful satin stretched across it. She glanced into the monitor and immediately placed her hand over her stomach and started sucking in. I understand that she’s a director and all but man alive, get yourself some Spanx or don’t wear such a clingy dress in a fabric that shows every single flaw.

    Sandra Bullock’s dress looked like it was designed by Liberace. Too much sparkle, too much sheen, too much gold/white/silver.

  14. bellaluna says:

    Queen Latifah looked beautiful, and I’m glad you mentioned Rachel McAdams, because I really thought she looked beautiful, too.

    Sandra’s dress is beautiful on her; Kristen Stewart looks like she either got a stylist or got a new one; Penelope’s dress is an absolutely gorgeous colour on her, but the style seems a little overwhelming on her. Demi, just no. Too thin, too much dress, too pale a colour on her.

  15. lucy2 says:

    I liked all of those, but was so-so on Demi’s. I also liked Kate Winslet’s, it was understated, but perfect for a presenter. Had it been for a nominee, I would have thought it too bland.
    LOVED Meryl’s, on anyone else it might not have worked but she looked awesome.

  16. Kolby says:

    I don’t think Kristen Stewart’s dress fits her properly. My favorite for the evening was Tina Fey. Her dress was beautifully cut and had just the right amount of sparkle.

  17. hmm says:

    I have to agree that Queen Latifah looked amazing. The dress fit wonderfully and the color was gorgeous against her skin. But, Demi, she was way too skinny and when she walked on the stage she seemed to be having a little bit of trouble handling the dress. Of course, I loved Sandra and I too feel like Pene always wears a variation of the same thing.

  18. fifi says:

    how could you have NOT included gabourey sidibe in this? she looked like a dream in her dress!!!

  19. JulieNewmar says:

    What the hell was going on with Sarah Jessica Parker’s hair? Flyaway and looked like it was coming unravelled. Was there no one around with a comb and some spray/gel?

  20. The Queen Bee says:

    Why are all the pictures you used for this post so bad? The one of Cameron is just plain awkward, Penelope looks startled, Kathryn’s arm is moving in hers… With so many good choices why these? Were they cheap?

  21. Jazz says:

    Liked Cameron Diaz’s dress, QL, Kate Winslet and Kathryn Bigelow. Hated Demi’s dress and JLo’s.

  22. Mouse says:

    Yeah, the only dresses I liked were Penelope’s, Sandra’s, Meryl’s, Gabourey’s, and Queen Latifah’s. Nothing and no one else really stood out. Except Diaz’s back fat on stage.

  23. boo says:

    Queen Latifah looked best to me. Her dress was gorgeous and fit her well.

  24. nikki says:

    Meryl, Bullock,Latifah and Stewart were the best-looking for me

  25. Other Laura says:

    Loved Cameron’s dress. and I absolutely loved the colour of Penelope’s dress.

    Kristen’s dress doesn’t seem fitted to her…does that make sense? And she looks dressed up from the neck down and everything else looks haphazardly thrown together.

  26. Cheyenne says:

    Yes to Bullock, McAdams, Diaz and Bigelow. Wasn’t too crazy about Latifah’s dress. And Streep is a great actress, but that dress looked like she was channelling her inner Mamie Eisenhower.

  27. Ruffian9 says:

    Looks like someone has been on a cleanse fast for a few weeks…eh Demi?

  28. kelbear says:

    Love Love Love Sandra and she hit it perfectly. She looked amazing!!! Like Meryl Streep also but didn’t like her hair as much.

    Rachel McAdams looked amazing! Love that dress so much, if I had a reason too, I would wear it!

  29. LOVE ANGELINA says:

    LOL I hated Cruz’s dress. To much fabric. I hate Rachel McAdams look as well.

    Loved loved Meryl’s look as well. So thrilled to hear Chris March from PR designed it, loved him on PR.

    Loved Cam’s look, it was gorgeous darling.

    Queen Latifah did look stunning, loved her look.

  30. michellllle says:

    The older woman did it best. Helen Mirren & Meryl were just beautiful.

    Queen never looked better, hair, make-up, dress in shape & color, all around gorgeous.

    Sandra was so pretty, loved the hair. Finally, Penelope was stunning but when isn’t she? McAdams & Monique also looked fab.

    Off the topic, but why did Demi present?

  31. Maritza says:

    Cameron Diaz and Rachel McAdams dresses are my favorites. Demi’s toothpick legs look awful in that dress.

  32. snapdragon says:

    my favorite of the night has to be queen latifah. she got it exactly right: pretty dress in a gorgeous color for her, beautiful makeup, classic hair, understated accessories and the dress fit like a glove. also, she is rocking the hourglass shape and she just looks really happy and relaxed.

  33. L says:

    All I could notice about Diaz, was how different her face looked. Even my husband who is blind to stuff like that was all ‘why aren’t her forehead and cheeks moving?’ Looked plastic.

    I loved penelope’s dress. Great shape and color. I think Rachel McAdams needs to dye her hair back to brown.

  34. Trillion says:

    Demi looks very hungry. I’ll go ahead and help myself to another waffle for her right now.

  35. Icecat says:

    It’s funny. Radar Online’s picks for best and worst are completely opposite of yours.. :)

  36. Rachel says:

    Vera Farmiga’s dress didn’t photograph well, but it looked really good on her when she walked the red carpet. It moved well. Conversely, Meryl’s dress did not look good live, but photographed beautifully. In fact, I was shocked by that picture because when I saw her last night, all I could think was “Meryl, who put you in a pillw case?!” I was also disappointed that it was so similar to the other dress that Chris designed for her.

  37. Green Is Good says:

    Helen Mirren as always looked so elegant, I was bowled over.

  38. ChristianH says:

    2 things: 1) Where’s Helen Mirren?

    2) Sandra Bullock looked like a mannequin.

  39. daniel says:

    Demi’s breasts were coming out.

  40. chicoulina says:

    My favorite was Demi’s.Maybe it’s because I’m European,who knows?I loved her shoes!When she walked on stage I gasped.
    I also gasped when I saw Queen Latifah.That’s her best look ever!!
    I didn’t like Sandra’s hair or lipstick.I think she looks best with natural makeup and her hair up.Not crazy about the dress.She could have done better.
    Meryl’s hair was beautiful,white looks good on her.The fabric looks kind of cheap.But Chris March did a good job.I like the fact that she’s wearing long sleeves.
    Kathryn Bigelow looked amazing!What a great figure!The woman is 58 years old!I was shocked!!
    Hilary Swank was a goddess!What a body!
    Anna Kendrick’s was okay,the shows were wrong.
    Mariska Hargitay was beautiful.
    I loved Nicole Richie’s dress!I want it!
    Cameron and Penelope were blah to me.I prefer Cameron with bright colors and Penelope with her hair down.She does not look good with her hair up.

  41. juiceinla says:

    Except for Demi’s hooker shoes (which lost the Oscar for “Most likely to earn a girl a $20 on Santa Monica Ave.” to Maria Belos Stripper shoes), I totally agree with you!

    Finally I like a Merle dress. swoon! “Beautiful cut on the dress (designed by Project Runway alum Chris March,”- yesh! Bravo!!!

  42. mollination says:

    I loved Demi’s too. It was one of the only ones I caught on stage (only caught the tail-end of the show).

    Also- DANG katheryn bigelow is beautiful. She looks a lot like Kim Raver to me..

    And lastly – a little unfair that you’re going to rag on Elisabetta Canlis’ wrinkly dress, but let Queen Latifah get a pass.

  43. chicoulina says:

    Mollination I totally agree with you.Everytime I see Katheryn Bigelow I think I’m looking at Kim Raver which I love!

  44. Kim says:

    I thought Sandra dress looked matronlly and was NOT flattering to her body type at all. Also her hair should have been up in this dress with all the beading at neckline and its pretty bold to wear adress that looks like an Oscar – can you say I know Im going to win? I like Sandras personality but that was NOT an Oscar deserving role at all. Penelope looked awful. Meryl looked great

  45. Stella says:

    Demi Moore- NOT AGE APPROPRIATE. She’s trying way too hard to look young, that dress would be much better suited on a 20 something.

    Sandra Bullock — Johnny Weir called and wants his ice skating costume back.

  46. Kim says:

    I agree Demi looked great and Queen Latifah looked best Ive ever seen her.

  47. Kim says:

    Cameron Diaz looked like a 50 yr old stepford wife. WAY to matronlly on her.

  48. Kim says:

    LOOVVVEEEE Demi’s shoes. They are gorgeous!

  49. Kim says:

    Is Clooneys girlfriend a man? Seriously she is very masculine looking in th e face and those hideous hooker arm band tattoos are so declasse. She looked terrible and miserable at the awards. She needs to learn to smile for the cameras or maybe she knows her 15 mins as his girlfriend are about up?

  50. Camille says:

    Spot on Kaiser! I agree with you on everything in this post, well said!

    I also really liked Elizabeth Banks dress, although I didn’t like the hair style on her.

    Did anyone notice how many actresses all had the same hair style? It must be the new ‘it’ hair style. Basically it was a bun, and the front of the hair was kind of loose (worst offenders of this look were J.Lo and SJP who had really bad flyaways).
    Sandy B and Cameron D were the only ones that seemed to have their hair different (just plain old down), but they stood out more because of it IMO.

  51. Eden says:

    Sandra Bullock looked amazing. Demi Moore looked awesome, but explain something to me. Demi is 47 and ROCKS a kicking body – absolutely beautiful!!! But, Suzy Amis (James Cameron’s wife) at 48 looks like the Crypt Keeper! Does she not own a mirror or know a great plastic surgeon???

  52. Jo 'Mama' Besser says:

    Demi’s dress is the impoverished man’s version of the Versace feather gown.

  53. noonoo says:

    Kathryn Bigelow looks incredible. Full stop.She wins. Everyone else go home.

  54. Cletus says:

    Demi needs her knees worked on again. I have seen better ones on an elephant.

  55. corine says:

    Ok, I may be in the minority, but I like Cameron’s dress. It looked very Marilyn Monroe to me. I like Sandra’s outfit, altho she looked too much like a shiny statue. Rachel McAdams’ dress was very pretty. And, Meryl Streep’s dress looked really good on her.

    Everyone else–I hated–sorry.

  56. Ale says:

    I wasn´t particularly fond of Bullock´s dress, never thought she could look Bland and she seems tired, sad and totally not in the mood, how unusual of her. She always looks so enthused and happy, and had looked radiant throughout all of the awards season. Maybe she tried to go with something too elegant because her oscar win was practically locked but she doesn´t look like the same Sandra America has fallen in love with. What happened?

  57. CB Rawks says:

    I think they asked Demi specifically so that she could do the In-memoriam to Patrick Swayze. (I wish they had focused on him more. But hey, how the hell did they forget Farrah Fawcett?! That was bad!)
    I liked Demi’s outfit but when she was on stage at the mic, her boobs were spilling over and looked crushed tightly in the dress, so it was not a very good fit.

  58. Yowsers says:

    Bigelow? Interesting proportions on her — most women have bigger hips and slimmer shoulders, but she’s the opposite and has shoulders like a line backer here.

    I kept thinking she was on the verge of going where Madonna went so many years ago — too much time in the gym!

  59. K McFarlane says:

    I thought Demi looked old. And she NEVER looks old. The color washed her out. Not her best look.

    Sandra looked fantastic, as did Penelope, as did Vera Famiga, as did Meryl, as did Kathryn. And Rachel McAdams looked a little washed out but still beautiful. Amazing dress.

  60. Aspen says:

    Queen Latifah is one of the most beautiful women EVER. She doesn’t seem to age, but she is maturing beautifully. I don’t think I’ve ever seen her at an event when she wasn’t just stunning. God, I hope I look that good when I’m her age.

  61. dinosaur says:

    I liked Meryl Streep’s, Penelope Cruz’s, Cameron Diaz’s, Kathryn Bigelow’s and Queen Latifah’s gowns. I particularly thought Penelope looked really pretty on that dress. Rachel McAdams had an interesting choice of a gown and I thought she looked very pretty in it too.

    I was not a fan of Sandra Bullock’s shiny get-up. Maybe it’s because I’m used to see her in far simpler, classic dresses but I thought she looked a bit like a disco ball on prom night. Her make-up was not the best either. Kristen Stewart looked so miserable throughout the ceremony that it was hard to appreciate what she was wearing; in retrospect, it’s alright, although it looks a bit baggy and awkward at the top. Demi Moore’s, however, I found horrid. It was a bad color choice and far too frilly.

  62. amar says:

    Chris March should dress Meryl Streep for everything she does from now on she looked great at the Globes and wonderful at the Oscars

  63. Ashley says:

    You know Demi and Cameron didn’t pick those out right? Rachel Zoe dressed Cameron and Demi. Seriously Rachel Zoe has the eye because her dresses constantly get picked for Best Dressed. If it was up up those two… well we’ve all seen what they looked like before the Zoe.

    Although Demi’s dress was made for someone younger. She also looks way too skeletal.

    *Edit didn’t notice she styled that ugly Saldana dress. Yikes. Her game was off on that one. Maybe she was overstrecthed this year? I guess we’ll see it on next seasons show.

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