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, Crocs — 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. This is just our small selection of hideous footwear. You can see the entirety of this list at the New York Magazine website.
Iris Schieferstein Vegas Girl I Heels, 2009
Jean Paul Gaultier 1977 Les Plongeuses Fin-Heels, S/S 2007
Crocs, 2002
Photo:Cate Gillon/Getty Images
Kobi Levi Double Boots, 2000
Anna Korshun Gray Ankleboots, 2010
Nicholas Kirkwood for Meadham Kirchhoff Lamé Platform Sandals, S/S 2012
Mihai Albu Structures and Megastructures Shoes, F/W 2010
Vibram Five Fingers, 2005
Prada Acrylic and Crystal Sandals, S/S 2010