Since it’s my first time celebrating Halloween here on the blog, I wanted to do something BIG for you guys! To be honest, Halloween isn’t my favorite holiday (I’m crazy about Christmas!) but I do love it nonetheless. In high school, I loved doing the football dress up days with Student Council. I have so many memories from coming to school dressed like a total wacko, from tourist day, to elderly-person day, to superhero day. You name it, I’ve probably dressed up as it at some point in my life! Anyway, if you read my post on my DIY Twiggy halloween costume, you know I’m inspired by legendary style icons this Halloween season. I wanted to give y’all one last dose of costume inspiration before the 31st. So I knew I had to dress up as the queen of the fashion industry, Editor-in-Chief of American Vogue, Anna Wintour.
I’ve seen the Anna Wintour Halloween costume idea popping up on social media lately, so I’m excited to show you my take on it! This shoot was so much fun because I loved channeling Anna’s personality. When I dress up for Halloween, I literally don’t even think of myself as Ashley anymore. I take on every aspect of the character, including their clothes, posture, and way of speaking. Suddenly, I AM THEM. Lol! With that said, I hope you like this Anna Wintour halloween costume idea!
For this Anna Wintour halloween costume, the most important aspect was the wig and sunglasses. Those are Anna’s signature, and what make her recognizable. Anna’s bob is iconic, and you bet she’ll be wearing sunglasses while seated front row at fashion shows. A quick Google search led me to this Anna Wintour wig from Pure Costumes. It was literally the perfect length, and is legit called the ‘Fashion Diva’ wig. Haha! It also paired well with these sunglasses I found at Walmart for $10. Anna always wears the same Chanel sunglasses with a very distinct shape, and these are pretty close. Score!
For the outfit, I knew I had to go for sophisticated, classic, girl-boss vibes. Even though Anna is aware of every trend that emerges, she prefers to wear timeless, elegant pieces that are always modest and fitted. I scoured Goodwill for this $5 tweed blazer, and paired it back to this light pink pencil skirt that I already had. Anna likes to wear shirts with high necklines, so I layered the blazer over this old white shirt from my mom’s closet! I couldn’t forget about Anna’s go-to jeweled statement necklaces. After analyzing photos of her, it’s obvious she likes to layer two necklaces in particular! This pink jewel necklace from Forever 21 looks nearly identical to one of hers!
Lastly, you can count on Anna having a Starbucks cup in her hand while dashing from meeting to meeting in NYC. I tried to recreate the same look with this Starbucks cup. On the morning of the shoot, I literally drove through the Starbucks drive-thru just to get the cup. LOL! Look closely, and you’ll see that I even wrote ‘Anna’ on it. 😉
The most important Vogue issue of the year is the September issue. I already had the September 2016 issue with Kendall Jenner on the cover, so I threw that in as part of the costume. It makes Anna look so important, and really adds something to the costume.
Thanks once again to Steve Ellinger for photographing this costume idea. Steve is always down to execute concepts with me (no matter how bizarre they are), which is awesome! This Anna Wintour Halloween costume is the most out-of-the-box shoot I’ve done since starting this blog last October. I’m curious what y’all think! Feel free to comment below, and let me know your first impressions! Also, what do you plan on being for Halloween this year?! Lowkey, I want to remember some of y’alls own ideas for next year! 😉