74 comments

  1. daniqueconijn

    September 17, 2007 at 5:49 pm

    love the dress
    love the haircut
    but i think,
    there is one hair that is pointing out.
    who is calling 911?!

  2. jamesy

    September 17, 2007 at 5:50 pm

    The dress is amazing…her hair is just dreadful. Such a lovely face HIDDEN, Anna what is the point??

  3. Anonymous

    September 17, 2007 at 5:51 pm

    I don’t care what anyone says about her. She ALWAYS looks fabulous. I LOVE that dress.

  4. RUDY

    September 17, 2007 at 5:53 pm

    FIERCE ! ! !

  5. Jack Daniel

    September 17, 2007 at 5:59 pm

    Lose that coat!

    I like her hair and her dress.

    What a find, Scott!

  6. Anonymous

    September 17, 2007 at 6:12 pm

    Love the hair and the dress, shes cut it that way for years. But then again maybe it time for a change.

  7. 艾迪

    September 17, 2007 at 6:36 pm

    I love your blog
    so cool

  8. Anonymous

    September 17, 2007 at 6:43 pm

    Great shot. She looks wonderful, as usual, and has quite a presence. This is really what it is all about.

  9. Anonymous

    September 17, 2007 at 6:52 pm

    Wow. Totally chick. I’m afraid.

  10. Iheartfashion

    September 17, 2007 at 7:13 pm

    Oscar?
    Chic as usual!

  11. Candid Cool

    September 17, 2007 at 7:24 pm

    Anna looks great. She always looks great. All that money, access, and free Prada. I like that she has a signature look, like Lagerfeld they have a very iconic image
    -h

  12. Anonymous

    September 17, 2007 at 7:32 pm

    i think her hair is a bit dated, no matter how iconic.

  13. Anonymous

    September 17, 2007 at 7:37 pm

    I think Anna Wintour knows the business of fashion better than anyone else, but I have never seen her as a particularly fashionable woman.

    -W

  14. Mate0

    September 17, 2007 at 7:42 pm

    Congrats! You’ve found the rarest Pokemon card of them all!!!

  15. cannon_ball

    September 17, 2007 at 7:51 pm

    Her dress is Oscar de la Renta Resort 2008. She probably got the dress straight from the runway.

  16. Susan

    September 17, 2007 at 7:52 pm

    i get that it’s her signature hairstyle, but i’m sure there are more flattering cuts for her out there. otherwise she is always looking so well put together. great pictures sartorialist!!

  17. Anonymous

    September 17, 2007 at 7:53 pm

    Dare I say you even got a hint of [gasp]…
    A SMILE!

    Well done!

  18. paulo

    September 17, 2007 at 8:00 pm

    Anna beautiful as always. I wish I could see her shoes-that would be the cherry on the top. Great shot as always Scott.

    -Paulo

  19. landis

    September 17, 2007 at 8:11 pm

    ok, even with all anyone will ever say about her. . .the girl knows her way around a print.

  20. JO

    September 17, 2007 at 8:14 pm

    BEAUTIFUL DRESS… I love it! It would look fabulous with my new red shoes.

  21. mwade

    September 17, 2007 at 8:16 pm

    for those of you calling anna “outdated”- she is fashion, if she’s outdated everyone is outdated. there is a huge difference between outdated and iconic and timeless. anna fits the description of iconic and timeless to a tee…

  22. marie

    September 17, 2007 at 8:34 pm

    Anna Wintour actually looks happy in this photo! :)

    I love her style!

  23. Anonymous

    September 17, 2007 at 8:45 pm

    Dress is beautiful but something is missing…. perhaps Carine Roitfeld?

  24. Anonymous

    September 17, 2007 at 8:55 pm

    Nice print.

    I think she hides her face with her hair so as to insulate herself from the masses of people staring/taking her photo/plotting to rip off/besmirch her fur coat at the next opportunity. Poor woman, she’s a walking symbol of the fashion industry. It can’t be easy.

  25. Anonymous

    September 17, 2007 at 9:18 pm

    I am so jealous of the way that dress really accentuates her figure. Perfect! Such a gorgeous look.

  26. Anonymous

    September 17, 2007 at 9:19 pm

    she’s so slim, and looks so chic!!!!!!!!!

  27. iopine

    September 17, 2007 at 9:25 pm

    If only she’d update that tired hair.

    There, I said it.

    I’m catty.

  28. Anonymous

    September 17, 2007 at 9:28 pm

    Anna WINTOUR!!! Say no more. What can I say. I have a thing for smart, fashionable and powerful women.

    I’d love to melt her icy cap… see what I mean?

    Great shot Scott…

  29. Anonymous

    September 17, 2007 at 9:57 pm

    she is always so beautifully dressed. and i love her signature hair :)

  30. The Nerdy Fashionista

    September 17, 2007 at 10:02 pm

    Anonymous said…
    I think Anna Wintour knows the business of fashion better than anyone else, but I have never seen her as a particularly fashionable woman.

    I agree completely!

  31. Blaise

    September 17, 2007 at 10:04 pm

    I can’t believe Anna Wintour have had that hairstyle since she was 14.. I like the dress though, both the prints and the fit..

  32. Anonymous

    September 17, 2007 at 10:10 pm

    HAhaha….pokemon… :)

  33. Anonymous

    September 17, 2007 at 10:35 pm

    You’re a sly devil, Mr. Sart.

    – desertwind

  34. E. Ross

    September 17, 2007 at 10:54 pm

    F-A-B-U-L-O-U-S!!!

  35. Françoise

    September 17, 2007 at 11:45 pm

    Anna Wintour. I love her and hate her. She does not leave anyone indifferent, does she. :)

  36. Anonymous

    September 18, 2007 at 12:00 am

    A.Wintour´s hair style is personal.Why change it? But why is she always wearing sunglasses-inside and out? Is it a `modern´fan?

  37. Pistachio Of Liberty

    September 18, 2007 at 12:40 am

    I find her boring. The dress is okay. I mean, it’s beautiful but *yawn* tasteful as usual zzzzzzzz.

    I agree with Susan. I can’t believe there is not another haircut that would flatter her. Trademark, schmademark – I would go CRAZY if I didn’t try a new cut every few years, especially working in an industry whose middle name is novelty. [I don't know what it's last name is. Visabill?]

  38. curiouskaryn

    September 18, 2007 at 1:22 am

    wow. You must weave some kind of magic with that camera. I can’t imagine her majesty posing for anyone on the steps of Bryant Park. You’re a god for getting her to pause. Is this a guerilla ambush shot or is she a friend?

  39. Anonymous

    September 18, 2007 at 3:20 am

    All that’s missing is a pair of horns on her head.

  40. pig_93

    September 18, 2007 at 3:49 am

    She knows how to carry a print.

  41. Modediktator

    September 18, 2007 at 4:14 am

    Wow, her royal highness Anna!
    What a fabulous find!!

  42. LostInTranslaton

    September 18, 2007 at 4:15 am

    I would kill for a bad photo of her! Or have the photographers been already killed?

  43. Cut of cloth

    September 18, 2007 at 5:01 am

    Iconic as usual
    And what a
    Fabulously Tiny
    Waist
    Rock on ANNA

  44. KEYNOTER

    September 18, 2007 at 5:37 am

    Wow, what a dress and figure. Love the dark print dress and the light coloured mack over her shoulders. Very cool and breezy. The colouring of her clothes matches her hair and glasses perfectly. Both of which allow me to recognize instantly the lovely lady in your shot.

  45. Anonymous

    September 18, 2007 at 5:58 am

    She is simply the best!!!

  46. angela

    September 18, 2007 at 6:21 am

    The print on the dress looked like bats to me. I saw this and thought “Halloween.” Not necessarily a bad thing, I’m just sayin’

  47. raleigh

    September 18, 2007 at 8:16 am

    always perfect

  48. simplyolive

    September 18, 2007 at 8:51 am

    can someone please update her hair!?
    it’s a bit much for her fine features–it’s as if she’s hiding behind it.

    otherwise, her dress works…

  49. Anonymous

    September 18, 2007 at 9:26 am

    I agree with Jamesy. Isn’t it time for a new do, Anna?

    Dress is fab. The shows were all about Native prints – ikat etc. Anna, of course, is already there.

  50. Trendini

    September 18, 2007 at 9:26 am

    anna scares me

  51. Sadia Bruce

    September 18, 2007 at 9:32 am

    My grandmother and mother would have worn variations of this outfit– sans trench– to grocery shop in 1960s Cebu City. (See profile photo.)

    Love that print.

  52. sandman_gr

    September 18, 2007 at 11:19 am

    Perfect Wintour as usual! Your photo rocks!

  53. Anonymous

    September 18, 2007 at 12:04 pm

    I agree with several others here: the problem with the hair is that it overwhelms her. she looks like the stereotype of someone who’s gone into hiding, wearing a big wig. The glasses of course add to that effect.

    However, I like the dress on her: a small woman pulling off a rather large print.

  54. Anonymous

    September 18, 2007 at 1:10 pm

    Fabulous dress; great figure; love the glasses, but, but I thinks it is time to do something different with the hair. It is starting to look a bit dowdy.

  55. Rachel Galperin

    September 18, 2007 at 1:27 pm

    i’ve never seen the devil wears prada, but my momma always told me not to judge people before you’ve met them. Love Anna and love the dress. She always looks lovely. And i obviously love vogue!!

  56. Anonymous

    September 18, 2007 at 1:58 pm

    yeah buddy, that’s what i’m talking about, mature hotness.

  57. daniel

    September 18, 2007 at 2:01 pm

    She is absolutely gorgeous. What a knockout, wow, I just love her look, her hair, that dress, everything. She is divine.

  58. Asian Models Blogger

    September 18, 2007 at 3:11 pm

    The priced catch! She looks fabulous. I don’t know how she does it.

  59. jkrnyc

    September 18, 2007 at 3:19 pm

    Pistachio of Liberty: “working in an industry whose middle name is novelty. [I don't know what it's last name is. Visabill?]” ROTFL!

    I second all those who call for new Anna hair. This do is tired, signature or no.

  60. nycinside

    September 18, 2007 at 3:24 pm

    I’m surprised she’s not sporting a Federer.

  61. Pistachio Of Liberty

    September 18, 2007 at 4:33 pm

    That’s the thing – generic soccermom hair and dark glasses say, “No, please, don’t recognize me!” – while at the same time making dang sure she is instantly recognizable.

    And Pokemon, heh.

  62. simplyolive

    September 18, 2007 at 7:30 pm

    nycinside…

    you made me laugh!

  63. riz

    September 18, 2007 at 8:19 pm

    the dress solo would have made a more powerful statement – or replace the coate with an amazing cardigan??

  64. I. Sophistique

    September 18, 2007 at 9:59 pm

    Anna looks fabulous here. She does prints very well.
    And the cut of her hair is always impeccable

    Loving it.

  65. JSB

    September 18, 2007 at 11:43 pm

    Anna Wintour, we love you!
    (We as Me, myself and i.)

  66. KimLeeStar

    September 19, 2007 at 3:00 am

    drops dead!!! WHEW!!! amazing!!!

  67. Anonymous

    September 19, 2007 at 4:28 am

    I think to say she looks boring is very short-sighted. Anyone can wear over the top fashion clothes from Gareth Pugh. Anyone can wear Balenciaga straight off the runway even if it does not suit them. The trick is that Anna dresses for herself, for her style and never changes her look regardless of the fashions around her. She appropriates key pieces and makes them her own which makes her a truly stylish person. Also it must be noted that she is a 50 something year old woman who literally wears clothes straight off the catwalk (i.e. she fits a dress that was last worn by a 17 year old). She is everything you need in a fashion icon. True style is not about being dictated to it’s about listening and then doing what is right for you.

  68. Anonymous

    September 20, 2007 at 10:22 am

    She’s looking so much better since she’s gained a little weight–she looks healthy now, more relaxed, and less like a scary fashion robot.

  69. Anonymous

    September 20, 2007 at 12:34 pm

    anna who?

  70. Elaine

    September 20, 2007 at 2:10 pm

    That is a great pic. How did you get her standing so still and so willing? I am impressed. I love the lighting on her coat. Beautiful.

  71. Ando

    September 20, 2007 at 10:24 pm

    i dont care what people say about her. She always looks amazing.

  72. Anonymous

    September 22, 2007 at 5:31 pm

    I LOVE Anna Wintour!!!!!!!!!!!!!

  73. b.stylish

    September 24, 2007 at 2:24 pm

    Is she HER?? really Her??

  74. Anonymous

    October 6, 2007 at 12:12 am

    And at this very moment, I realize: I WORSHIP THAT WOMAN.

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