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Over the course of my life, I’ve made many, many, many attempts to become a loafer person. They’re just so chic! And timeless! And currently, right on trend with the resurgence of prep school style. But after a day’s worth of attempting to break in a shiny new pair (because any longer would result in painful blisters), I always relent to my more comfortable sneakers, boat shoes, or supportive sandals. That said, the desire to wear a polished loafer with a relaxed pair of jeans and a simple white T-shirt never left me—and so began my search for the most comfortable loafers.
What is it that makes loafers so tough to break in? According to shoe and clothing designer Jamie Haller (and the woman behind my favorite pair of loafers, which I happen to be wearing as I write this story), it’s all in the structure of the shoe. “I began making [my] shoes by removing all of the counters, which is the cardboard-like material that lives in between the two layers of leather in the shoe and usually provides form and structure but can also be hard and uncomfortable,” the designer shared. Based on first-hand experience, I can confidently say she did it right. “These structural changes really set us apart along with the old-world style of construction that offers a soft glove-like fit. We utilize soft, supple skin and Sacchetto construction (“Sacchetto” translates to little bag) that creates a contoured fit that molds to your foot,” she said.
Of course, she’s not the only one to make comfortable shoes; there are plenty of easy loafers to slip on in bliss—and I used my own experience and crowdsourced my colleagues to find the best. Shop them all, below.
Dale Arden Chong is the Senior Fashion Commerce Editor at ELLE.com. Previously, she was an editor at MensHealth.com and has written for Who What Wear, GLAMOUR, The Coveteur, and more. She loves fashion, food, and art, among other things—but her greatest love is K-pop idol V of BTS.
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