The Only Boot Trend That Matters, According to Anna Wintour

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Anna Wintour is nothing if not a creature of habit. She's a die-hard loyalist to her oversize sunglasses, Chanel red carpet looks, and Manolo Blahnik strappy shoes, all of which she's been wearing on repeat for years. That said, she still likes to mix up her wardrobe with seasonal items, and every fall, she reliably reintroduces her favorite boot trend of all: knee-high leather boots with stacked heels.

In fact, she owns five different versions of the trend, and I couldn't find a single photo of Wintour wearing any other boot style this season. She packed plenty of versions for fashion month, from the slouchy burgundy ones she wore to the Chanel show to the head-turning snakeskin versions she wore in London. Most recently, she wore classic tan boots to a tech event in San Francisco this week, proving that they're versatile enough to work outside the street style bubble.

And in case you're wondering, there's only one Wintour-approved way to wear knee-high leather boots: with a printed midi-length skirt or dress, naturally. Other clothes need not apply. Scroll down to see five ways she's worn the boot trend and shop the look at a variety of price points.

How Wintour Wears 5 Different Versions of the Trend

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Shop More Knee-High Boots

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.