There are all sorts of reasons that shoes turn ugly. And all sorts of reasons we turn to ugly shoes. Feet, themselves, are an anatomical oddity, and ugly shoes either sacrifice aesthetics for podiatric practicality, or ignore function for the sake of fetish and fashion fantasy.
With either, it can quickly go too far: Sometimes a shoe is too avant-garde for its own good, with some of the best footwear designers (ahem, Miuccia Prada) putting pairs down the runway that you won’t be blowing your paycheck on. In other cases, comfort comes at the expense of fashion, and the results – UGGs, Birkentstocks, Doc Martens – end up homely.
Still, fashion is fickle; one day, any of these styles on our list may be cool again, or at least ironically embraced. For now, they prove that there are far more ugly pairs in the world than pretty ones. And because we all own some ourselves, tell us what’s missing in the comments section.
View the top 50 ugliest shoes in history gallery at nymag.com