Anna Wintour's Airport Outfit Includes the Shoe Trend I'd Never Travel In

Anna Wintour is nothing if not consistent. Of course, you already know that she's worn the same sunglasses and bob haircut for as long as she's been EIC of Vogue—which is to say, a very long time. She also never wavers from her signature outfit formula: a printed midi or maxi dress with knee-high heeled boots. And as it turns out, this is true even when she's traveling through JFK Airport in New York.
I've never worn heeled knee-high boots while traveling because I can imagine that taking them on and off at security would be quite a hassle—would the chic yet cumbersome shoes even fit properly in a tray? And you certainly won't catch me wearing heels of any sort while travelling, as schlepping through airports is already an exhausting experience that would only be made worse by wearing anything remotely uncomfortable. Anna Wintour definitely looks just as chic as ever, but I personally would think twice before wearing her shoes at the airport. Scroll down to see her airport outfit and shop for more comfortable boot alternatives.
Shop My Favourite Flat Ankle Boots for Travelling
Ground your looks with this chunky pair.
Next, Victoria Beckham Just Made Leggings Look Posh With These Unexpected Shoes.
This post was previously published and has since been updated.

Erin got her start as a Who What Wear intern in 2011—back when the site only published a single story per day. (We have since increased that number twentyfold.) She graduated magna cum laude from USC and lives in Los Angeles. 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 2015, where she is now the Associate Director of Fashion News. From the Oscars to the Met Gala, she leads the site's entire red carpet coverage strategy. She specializes in celebrity and fashion news but also enjoys writing travel features and runway reports. She frequently contributes to WWW's social accounts and has a sizable following on her personal TikTok.
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