But what makes a gym shoe transcend its athletic purpose and become an athleisure sneaker? While there is no firm line, I looked for shoes that could pair just as well with trousers and skirts as with yoga pants and sweatsuits. Sometimes, that meant finding shoes with unexpected detailing or fashion-forward color combos. Other times, it meant finding those so-uncool-they’re-cool shoes that have gone from dad shoe to cool girl streetwear.