Halloween Throwback: Anna and Grace

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Toddler dressed up like Anna Wintour for Halloween, holding an issue of Vogue Magazine

With Anna Wintour no longer Editor in Chief of Vogue (she is now global chief content officer and artist director at Condé Nast), it made me think of Halloween 2013 when I dressed my daughter up as Wintour, and I Grace Coddington. I thought I'd share it as a bit of a Flashback Friday in honor of the holiday!

Four-year-old girl dressed up like Anna Wintour with a bob haircut, large sunglasses, a polka dot dress and oversized pearl necklace

Emerson already had the haircut and the dress, I loaned her a pair of my most oversized sunglasses and my Stella & Dot pearl statement necklace (I still have that necklace and we kept the dress in a memento box for her!).

Mother daughter halloween costume of Grace Coddington and Anna Wintour

We already had the wig, I just brushed it out a bit. Added very pale makeup and lightened my brows with concealer to look a bit more like Grace Coddington. I did need to hold the book for folks to know who I was trying to be; everyone immediately recognized my daughter. Below is the original text from this 2013 blog post:

Mother daughter halloween costume of Grace Coddington and Anna Wintour

My friend Kim sent me this link from the blog Oh Happy Day! With a daughter whose hair cut we call “The Anna,” it seemed like a perfect choice to have her dress up as Anna Wintour for Halloween. Emerson and I thought it would be fun to dress up together, so I brushed out a Glinda wig, put on my black comfort sandals and my darkest lipstick to be Grace Coddington.

Things I learned from this experience:

  • Bloggers must bribe their children to do all the adorable shoots that they do. We used M&Ms and even so these are the best pictures we could get in the couple of minutes before it stopped being silly fun for Emerson and became work.
  • It’s hard to be a soft curvy woman and dress up like a slim wirey one. I just look like Old Mother Hubbard with a bad dye job!
  • Wigs are HOT!
  • I don't seem to own a single pair of big plastic sunglasses.  These are old scratched ones and I colored the silver parts black with a Sharpie.
  • Emerson can’t make a “mean” face no matter hard she tries, and she really tried. She saw pictures of Anna Wintour on Google Images and was excited to pretend to be the “fashion lady” and do her stern face, but a happy four year old can only look so stern before she falls into a fit of giggles!
A woman with curly hair wearing a plaid blazer holds a green fur coat over her shoulder on a city street.

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66 Comments

  1. I wonder if E would be willing to recreate this look now – she’s had some time to refine her sourpuss expression, lol!

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  2. This was the first time I had seen this, so am so happy you re-posted! I absolutely LOVE it. You both look awesome.

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  10. “Adorable” is a word that just doesn’t go with Anna Wintour….so I thought. Bur it’s the only word I can find to describe your little fashion lady 🙂 So so so darn cute and ADORABLE!! 🙂 Thanks for sharing!

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  11. This is absolutely the best thing I have seen in quite some time!!! How adorable is Emerson! I love her little faces!!! Definitely too cute and sweet to be a sourpuss!

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  17. Love, love, love this!! Little “Anna” is adorable. And, why aren’t you a redhead in real life? It looks amazing on you.

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    1. Thank you so much, but you wouldn’t imagine how much pale makeup I have on to look like The Cod! And the brows were hidden under concealer. I was a redhead before in high school and college and while I can pull it off, it requires a lot of makeup and only wearing certain colors to not look like death warmed over 🙂

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  29. Emerson is amazingly ADORABLE! She is a dead ringer for Anna…minus the mean mug! Great job you two!

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  42. THIS IS SO AWESOME!!! I knew exactly who you were as soon as I saw you. And Emerson is totally rocking the Anna Wintour look!! This makes me so happy!!

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  49. This has got to be the cutest Halloween get up I have ever seen! Emerson and her “stern” look is priceless! And you make a great Grace! Love this!

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  55. LOL! I was looking for pictures of Anna Wintour smiling earlier, and it was tough. So no wonder Emerson had a hard time staying so stern and NOT giggling – it’s tough business! Only for the toughest and meanest!

    Y’all look so, so great though. This is just darling.

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  58. Oh my gosh, this is the cutest thing ever! She’s a perfect Anna and I’m sure she had fun dressing so fancy! And you look awesome too! Just like “The Cod!”

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