How to: A Chic Halloween: DIY Anna Wintour Costume

Nothing would irritate Anna Wintour more than a knockoff Anna Wintour costume. Which is why I highly encourage them this year.

Let’s be honest. We all love Anna W., but can you imagine how fun it would be to watch her writhe with irritation, yawn dramatically at boring meetings, roll her eyes at your less than fashionable attempts at shift dresses with nude sandals?

I’m the biggest fan of Halloween you probably know, yet I’m as bored with polyester “sexy” costumes as Anna Dubs at the Faded Glory spring 2013 show. Why don’t we break out of the box and bring serious style into the most dramatic and mysterious holiday of the year?

Here, I use a few of Anna’s iconic favorites to tie in the look. The only thing you might need to specifically purchase is a light brown or dark blonde pageboy bob wig, but you could try a DIY faux bob instead.

• Shift dress: One of Anna’s favorites, you probably have a shift dress in your closet already. If not, they’re quite easy to find, and you could probably pick one up at a thrift store before Halloween weekend. Not into shift dresses? Try a bouclé or tweed skirt suit.
• Nude heel sandals: I’m sure Anna wears boots or leggings sometimes, but I’ve never seen it. I saw her wear black tights once, and I thought it might have been photoshopped. If you can’t bear to wear sandals on Halloween–if it’s remotely cold in your part of the world; here, it’s 80 degrees–just throw on a pair of nude pumps.
• Classic trench coat: Guarantee that you have one of these already! If not, get one. They’re impossibly classic and versatile. I picked up four amazing vintage London Fog trenches for my vintage shop recently, and I’d be happy to hook you up. Check out my Etsy shop, or contact me for more info.
• Gold collar necklace: This simple necklace works well with the high neck of a shift dress or tweed skirt suit and is classic enough to fool Anna. If you have a short strand of pearls, you can rock those instead.
• Bob wig: An absolute necessity. Without the wig, you’ll just look like a fabulous style blogger. If you don’t want to pick up a cheap wig, you can try a faux bob, but it won’t be as severe. And isn’t that sort of the point?
• Huge black sunglasses: Anna Wintour is on record stating the reason she always wears a pair of oversized sunglasses–so you can’t tell if she’s bored at a show. I quote, “They’re seriously useful…I can sit in a [fashion] show and if I’m bored out of my mind, nobody will notice. And if I ‘m enjoying it, nobody will notice… At this point they’ve become… really, armor.” Put on your biggest, darkest pair, and you’re good to go. Just make sure they’re not wayfarers, cat-eye, aviators, or another recognizable shape. Anna steers clear of these.