5 Foolproof Ways To Wear Loafers Like A Hollywood It Girl

These shoes have so many possibilities.

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NEW YORK, NEW YORK - MAY 10: Hailey Bieber is seen in Tribeca on May 10, 2023 in New York City. (Pho...
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It’s happened to all of us: You accidentally hit snooze one too many times — and now, there’s no way you’ll be able to carefully put together an outfit for work. So what shoes do you step into as you rush out the door? Nine times out of ten, probably loafers. Polished and practical, the footwear style is a no-brainer for the office. But, perhaps you’ve yet to experiment with the flat silhouette outside the hours of nine to five. If this sounds about right, take it from your favorite celebrities: There are so many outfit ideas you can make with the menswear-inspired footwear, and for myriad occasions.

Over the past few months, nearly every It girl has given the timeless accessory their stamp of approval. For starters, while visiting New York in early September, Hollywood darling Olivia Rodrigo paired her Miu Miu black penny loafers with a graphic tee adorned with Angelina Jolie’s face (you need to see it for yourself) and a white pleated miniskirt. The week after, Kendall Jenner took to the streets of Manhattan in the elevated silhouette, too. The 818 Tequila founder’s styling approach? She teamed the shoes with low-key separates, like a corduroy jacket and black slouchy denim.

Take a closer peek at recent these and more celebrity loafer looks ahead — and shop each outfit for yourself.

Kendall Jenner

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Whether you’re doing some Saturday afternoon shopping or hitting up a casual happy hour, Jenner’s off-duty loafer look is worth copying. In mid-September, the model was pictured in New York City wearing a pair of black loafers from The Row alongside the luxury label’s corduroy jacket and relaxed denim.


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Zendaya’s body-hugging mini dress here was the perfect juxtaposition to her luxe hardware-heavy loafers. To complete the low-key vibe, Euphoria actor opted for a colorful Louis Vuitton tote and shiny gold hoops. If you don’t have the patience to wait until the spring to recreate this outfit (understandable), simply incorporate a puffer jacket and tights into the look.

Taylor Swift

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Swift has recently become the poster child of academia fashion. (Perhaps due to her 2022 honorary doctorate of fine arts from New York University?) As such, it’s no surprise the Grammy-winning musician steered her loafer look (her chunky lace-up pair is from Malone Souliers!) in a preppy direction with the help of a striped button-down and baseball cap. Follow her lead, and you’ll be fully equipped to sit in Washington Square Park and blend in with the students.

Olivia Rodrigo

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As mentioned above, Rodrigo stepped out in Miu Miu’s black loafers while visiting the Sirius XM studios in New York City two months ago (during the city’s unexpected heatwave, we should mention). For the afternoon outing, the “Vampire” singer combined her shoes with a one-of-a-kind T-shirt and leg-baring skirt. Her black oval-shaped sunnies and bold red lips provided the ultimate finishing touches.

Hailey Bieber

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One thing to know about Bieber: She loves slouchy cut denim, and that doesn’t change based on her shoe choice. Here, she wore her go-to bottoms with square-toe loafers, a sporty jacket, and a understated baseball cap. In short? This is the ultimate weekend uniform.