Classic Penny Loafers Get Reinvented for Fall: 15 New Ways to Wear Them

Whether you’re gearing up for a semester spent in lecture halls or have long bid adieu to the student lifestyle, penny loafers—a back-to-school classic—should be high up on your fall shopping list.

Style them with pencil skirts for a more classic look or boyfriend jeans for a quirky casual outfit. Just check out these 15 stylish girls and you’ll be instantly inspired to invest in this fall favorite.

But before you do, here’s a fun fact about penny loafers: Did you know that the flats got their name when moms in the 1900s needed a foolproof place for their kids to store some extra change for a phone call? And yes, phone calls once cost a penny!

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Go classic with a button-down shirt, a miniskirt, and penny loafers.

Stockholm Streetstyle

The masculine flats are a perfect addition to an easy denim-and-button-down look.

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Dress up a pair of tailored shorts with a tux shirt and pointed-toe penny loafers.

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For the office, the leather kicks are a great stiletto alternative. Just slip into the style with a pencil skirt and blouse.

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Turn the preppy style on its head by pairing it with ripped skinny jeans and a leather jacket for an edgier look.

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With an LBD or classic coat, look for loafer styles with a bit of extra detail, like studs or a tassel.

Penny Pincher Fashion

A pair of patent loafers will make a casual layered outfit instantly more elegant.

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When rocking the classics for fall, like an LBD and camel coat, a pair of penny loafers are just the thing to bring your look to the next level.

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Overalls and loafers are an easy, casual outfit.

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For evening plans this fall, style your lace minidress with a pair of embellished loafers. It’s the perfect high-low mix!

My Style Pill

Whether you’re headed to a casual day at the office or brunch with your best girlfriends, pair your loafers with a classic silk blouse and straight-leg jeans.