Mary-Kate Olsen’s Best Footwear Moments, From Velcro To Flip-Flops

If you, like me, are an Olsens obsessive, then the aptly named is your site. Somehow, people track down the otherwise quite mysterious Olsens doing things like going to Fleetwood Mac concerts, crossing their arms pensively on smoke breaks. Most recently, they caught Mary-Kate stepping out with sister Elizabeth in a pair of Louis Vuitton Archlights, a sneaker-favorite of Jaden Smith that possesses the arch of a prima ballerina.


Mary-Kate is a fearless wearer of shoes both funky and deeply luxurious—she seems not to discriminate. Whereas Mary-Kate and Ashley generally have a frighteningly cool aura—I imagine eating one of their pebble scones, for instance, and accidentally spraying crumbs all over myself in front of them—there’s something about Mary-Kate’s footwear choices that put me at ease. A fan of the simple black flip-flop, for instance, her footwear is often an unexpected compliment to her style choices.

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Mary-Kate Wearing Loafers—Mary-Kate (and Ashley’s!) penchant for chic, understated footwear began at a young age. Now known for the classic black loafer they designed for The Row, it turns out they’ve always been fans. In the early ’90s, they wore these very Diane Keaton-inspired outfits of a pinstripe suit-print dress, dress shirt, and trousers.

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Mary-Kate Wearing Flip-Flops—Another classic shoe Mary-Kate is loyal to is the classic, black flip-flop. They are, after all, California girls at heart. There have been many good and unexpected flip-flop moments in the Olsen repertoire, including this most iconic ensemble of Mary-Kate in a blazer and wide-leg trousers that are just a shade apart, white button-up underneath, and New York bodega coffee cup in hand—all tied together by, what’s that!, a black flip-flop.

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Mary-Kate Wearing Velcro Sneakers—Leave it to Mary-Kate to show up to a Sotheby’s gala in velcro sneakers! In 2017, she arrived alongside her husband, Olivier Sarkozy, in a long black coat trimmed with cream-colored lace and white velcro Alexander McQueen sneakers. Lace and velcro, a surprisingly elegant, pleasantly octogenarian combo!


Mary-Kate Olsen's Best Footwear Moments

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Mary-Kate Wearing Cowboy Boots—Cowboy boots, much like the inevitable yearly resuscitation of boho, never die. In the early 2000s, during Mary-Kate’s time at NYU, she would often be seen around the city with Starbucks, a big Balenciaga bag, a symphony of sweaters, and black cowboy boots with turquoise accents.

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Mary-Kate Wearing Too-Big White Sandals—Garage wrote a piece last year about the time Kanye West attended 2 Chainz’s Versace Mansion wedding in a seafoam green suit and a pair of puffy slide sandals that were apparently worn in the Japanese style of Iki, where a person’s heel is hanging off the back of the shoe. This big-shoe, small-size proportional play is also frequently employed by Mary-Kate, who once wore bulky, white cage sandals that were just a bit too big for her.

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Mary-Kate Wearing Snakeskin Boots—At WSJ‘s 2018 Innovator Awards, Mary-Kate wore an oversized blazer coat, black satin pants, and red snakeskin Céline boots—a rare, welcome pop of color!

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