4 Outfit Tips I've Learned From Writing 21 Anna Wintour Stories This Year

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If you read my Who What Wear stories or follow me on social media, you might have picked up on some themes. I'm constantly writing about people, places, and things I'm personally passionate about, which is why you see a lot of stories related to tennis and British royals as well as Scandinavian and Latin American fashion content. Well, I'll let you in on a little secret: Anna Wintour is another one of my favorite topics to write about. So much so that I've written no less than 21 stories about her in the last 12 months. Yes, I counted.

I've covered topics ranging from Wintour's thoughts on job interview outfits to her favorite wardrobe basics, and you can bet her advice and style sensibilities have rubbed off on me. (I even realized that one of my Copenhagen Fashion Week outfits was a bit Wintour-esque, if I do say so myself.) Naturally, I wanted to pass along what I've learned to our readers, so scroll down for the outfit tips I've gleaned from covering every facet of Wintour's style.

Invest in a Statement Necklace

When it comes to Wintour's jewelry collection, it's clear she has a fondness for one piece in particular: the statement necklace. We're guessing she'd trade all the dainty rings and bracelets in the world for her signature neck adornment, as she's rarely photographed without one. 

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If You Must Wear All Black, Choose Interesting Textures 

Wintour very rarely wears black and instead relies on her rainbow assortment of colorfully printed pieces. When she does wear black, however, she keeps it interesting by mixing materials like wool, velvet, and suede. She also chooses pieces with fun embellishments like pearl buttons. 

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Find Your Signature Pair of Shoes and Wear Them to Death

Wintour has made no secret of her obsession with one specific pair of Manolo Blahnik nude heeled sandals that she's worn countless times over the years. I literally lost track of how many times she's been photographed in them while I sifted through photo agencies. The message here is clear: When you find your favorite pair of versatile shoes, don't be afraid to stock up on multiple pairs and wear them with everything under the sun. Getting dressed in the morning will be that much easier. 

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Never Underestimate the Power of a Printed Midi Dress

Dare I say Wintour loves a printed midi even more than her oversize sunglasses? The editor in chief loves her ever-evolving assortment of printed midi dresses, which she wears to everything from fashion shows to red carpet premieres. 

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Next, four trends everyone will wear in 2020.

Erin Fitzpatrick
Senior News Editor

Erin got her start as a Who What Wear intern over 12 years ago—back when the site only published a single story per day. (Who What Wear has since increased that number twentyfold.) She graduated magna cum laude from USC, which is how she ended up moving to Los Angeles from her hometown of San Diego. In college, she also interned at Refinery29, where she was promoted to editorial assistant and then assistant editor. After nearly three years at R29, she came back to WWW in 2016, where she currently holds the title of senior news editor (as well as the unofficial title of resident royal expert—in case you haven't noticed her numerous Meghan Markle and Kate Middleton stories). She spends her days trying to incorporate her idols, Anna Wintour and Roger Federer, into as many stories as possible. Outside of work, she loves tennis, classic rock, traveling, and smothering her dog with affection.