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From David Letterman in 1995 to Ayo Edebiri in 2024, here’s how uber-stylish folks have rocked loafers across the decades. —Yang-Yi Goh, style editor
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How to Wear Loafers
How do you wear loafers? That's a little bit like asking how to eat rice. There are endless varieties of the essential slip-on shoes to choose from, from classic penny loafers and swanky bit loafers to daddish kiltie loafers and daddish sneaker loafers. And those multitude of options, in turn, are each versatile enough to service a wide spectrum of outfits—casual beach looks, everyday office ensembles, big-night-out formalwear, you name it. So whether you're looking to suit up sans socks with your classic black Weejuns or hit the streets in half-calfs and Dr. Martens, we've rounded up 18 of the most stylish loafer moments of all time to help inspire your next major fit. —Yang-Yi Goh Click here to view the full gallery.
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