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19 Best ‘Ugly’ Shoes of 2020, From Dad Sneakers to Chunky Loafers

You know when a dog’s so ugly it’s cute? It’s cross-eyed, scraggly, and has a goofy sounding bark—but those unfavorable qualities somehow win you over, meshing into an adorable little package in the end. I’ve always admired people whose closets work like that. They’re so skilled at putting together offbeat outfits that are so wrong, they’re right. Embracing fashion faux pas can make a look ironically stylish, and a low-risk way to get it done is to reach for notoriously “ugly” shoes.

Reworking blacklisted styles is a favorite trick among the fashion set since the choice adds an unexpected twist and says you’re a rule-breaker and an individual—which is essential to having personal style. There’s something about knowing an item is off-limits and wearing it anyway that will never not be cool—so get inspired by five street style looks that will convince you to give dad sneakers, clunky flip flops and chunky loafers a second thought.

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