Nike Challenger OG Sneakers "I love a classic shoe I can run around the city in that also goes with almost everything. These Nike Challenger OG Sneakers ($90) are men's, but you can buy the smaller size. The waffle sole is retro in look but so comfortable you can wear them for miles!" — Lisa Sugar, founder Image Source: nordstrom.com Nike Challenger OG Sneakers $90 from nordstrom.com Buy Now