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This week Vogue‘s indomitable EIC Anna Wintour celebrated her 62nd birthday and more than a few fashion outlets took it upon themselves to dig through the archive of Wintour style and pull up her greatest hits and misses. I couldn’t help but get a laugh out of some of her ensembles (proof that the 80s wasn’t nice to anyone) and thought I would share some of my favorites.

Love her or loathe her, you can’t deny the impact that Anna Wintour has on the fashion industry. While I don’t necessarily agree with the opinion that she is the “final word” in fashion – it is true that her voice carries a lot of weight. I do admire what she does for young designers with the CFDA and while I still believe that U.S. Vogue is not nearly as progressive as it’s international counterparts, I nevertheless respect Wintour and her singular vision which is obviously paying off as her’s is one of the few U.S. based fashion glossies that doesn’t seem to be trimming pages or staff in the face of online competitors. What do you think of Vogue and Anna? What magazines and editors do you find most influential?

The Power of the Power Suit


Shiny in the 90s


Rainbow Brights


Casual Fridays


Fur Trimmed


Ruffles Are a Girl’s Best Friend


Making Moves



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    Jun 3, 2012, 04.04 PMby Maimeo882002

    hmm I don’t like her hair at all.

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    Nov 13, 2011, 07.15 PMby Daniel Parker

    I love her…. that’s all

  • Missing

    Nov 10, 2011, 12.22 AMby sewster55

    To add to this terrible dising… I can not stand her hair & I think it’s terrible when women don’t change their hair style over time… Because hey fashion editor, styles change! It’s not like this a great hair style for her either. It didn’t even look good when she was young.

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    Nov 9, 2011, 04.06 PMby Tracey McGowan Wirth

    Does she ever age?

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    Nov 8, 2011, 05.15 PMby Dume

    Is she wearing the same shoes in three photos? Just for that I’d say she looks awesome. You’d think she’s a three-outfits-a-day chuck-it-after-a-season gal…

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    Nov 7, 2011, 06.06 PMby andreadevis

    My personal thoughts negative or positive is the request. I have wanted to share what I think since this was posted. Alas, I am not, I am going to give you the responses of my hotter, European version of Gary Cooper, husband. After informing him that Anna Wintour is the editor in chief of a fashion magazine he asked, “Why does she dress like a clown?” After showing him photos of Diana Vreeland he stared dumbfounded, “Incredible!” My case is closed…

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    Nov 7, 2011, 03.37 PMby Nicole Kendra

    I wish all my old pictures looked that good. Lucky woman.

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    Nov 7, 2011, 02.49 PMby popbabe7

    Interesting to see her as a brunette!

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    Nov 6, 2011, 10.34 PMby raving

    None of those are really my style, except for that very first photo, pre-bob days I suppose.

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    Nov 6, 2011, 06.25 PMby piackdy

    It’s tempting to be bitchy about someone like Anna Wintour. But she’s not the fashion editor, she’s not a stylist, she’s not a designer. So there’s no reason to expect her choice of clothing for herself to be top notch. She’s probably powerful for other reasons.

    And besides, the fashion crowds don’t always seem to be the most fashionably dressed. They’re the Artist to the beautiful photos you see in magazines. Artists don’t have to be beautiful themselves. You also have to be suspect when most of the magazines feature youthful beautiful models. If they’re so good at dressing they shouldn’t need beautiful models to realise their visions.

    So I’m not going to judge her choices. All I’ll say is I’m envious of her access to beautiful garments, and the opportunities she’d have working in fashion to wear more outrageous outfits if she chooses to. Taste is personal. If it makes you happy and confident in yourself, who’s to say their tastes are better than yours.

    3 Replies
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      Nov 6, 2011, 09.43 PMby nouvellegamine

      i understand what you’re saying and i felt somewhat bad for being negative. but i am having a laugh at poor anna’s expense bc she’s fashionable as opposed to stylish. and while it benefits her economically to champion disposable, ever changing fashion, it gently offends my sense of style ;)

    • Blythe_large

      Nov 7, 2011, 01.41 PMby piackdy


      I would have to agree with you that Fashion is generally silly. Why would one favor something that looks silly over something that flatters just because it’s current season.

      A gem is a gem is a gem. Of course when our body changes shape, maybe some old gems are better kept on the hanger or pass on to someone else who can wear it better.

      But change for change’s sake Fashion? Not my cup of tea either.

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      Nov 7, 2011, 02.56 PMby themisslinds

      well put and very true. you don’t get to the point of running one of the most successful magazines in the world simply by wearing cute clothes.

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    Nov 6, 2011, 12.30 PMby fashionfreek

    Oh wow! 62! I love the pic with her and Bono! U2 are excellent;-) I like the first pic of her with the black top and gold necklace and then any thing after 2000 on her looks nice on her. She don’t look bad for her age:-). The 1995 pic with her white shiny dress makes her look underweight a little. Happy 62nd bday to her and she looks fab!

  • Missing

    Nov 6, 2011, 04.42 AMby rochelle49

    That gold and aqua outfit is awful!

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    Nov 5, 2011, 04.31 AMby nouvellegamine

    i’m sorry, i don’t like to be negative, but anna but lacks style and suffers from the whims of fashion.

    2 Replies
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      Nov 5, 2011, 04.46 AMby themisslinds

      i totally agree – and don’t get me started on her love for terrible footwear…

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      Nov 5, 2011, 05.49 PMby tinapickles

      I also agree. She’s appears to be a slave to fashion without being a trend setter. And picks some stuff that isn’t very flattering on her petite frame.

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    Nov 4, 2011, 08.07 PMby designerroya


  • Alicia_dirago_square_large

    Nov 4, 2011, 07.15 PMby Alicia DiRago

    Ack, these are hilarious!

    • This is a question
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