Fashion is in large part about pushing boundaries — outlandish color combos and patterns, accessories on top of accessories, and mixing and matching between stylistic genres. So seeing cats rocking sneakers with suits really shouldn't be too out-of-the-ordinary. Whether purpose being to stay on the up and up with latest trends and/or fresh look, or simply comfort for your barking dogs, a gang of celebs has been caught mixing the two. From regulars like Kanye West and Robert Downey Jr. to a slew who simply love to don Chuck Taylors with their formal garb, the somewhat risque look doesn't always work, but when it does — we can't hate at all. Nonetheless, we'll let you be the judge as we bring you A Brief History of Celebrities Wearing Sneakers With Suits.