While I might hurt some feelings here, I have to say that Florsheim (before it started collaborating) made the 1st, ugliest-shoe-ever, which was called "Reva"
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The World's Foremost Authority on Fine Footwear
The Shoe Snob Blog is the world’s foremost authority on fine footwear. Founded by Justin FitzPatrick. Want to learn about good shoes? You came to the right place.