Whether paired with workwear or casual threads, the lug-soled loafer is this fall's MVP. From its first steps onto the fashion scene in the 1930s, the penny loafer (nicknamed for its decorative leather strip, which was just big enough to stash a penny—the cost of a phone call at the time) was a hit with men and women alike, thanks to its comfortable fit. Now, the preppy classic comes in unexpected colour combos and gets toughened up with utilitarian lug soles and chain details. Scroll for twelve pairs of chunky loafers you'll want to wear all season long.
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Want to streamline your life? In our Spring 2025 issue, we’ll show you how—whether it’s paring down your wardrobe, decluttering your messiest spaces or spending way less time cooking thanks to an easy, mostly make-ahead meal plan for busy weeknights. Plus, our first annual Pantry Awards.