Spice up your sneaker selection with the Converse Jack Purcell Mid Boat Shoe ($70). These stylish shoes feature a mid-cut with a moc-toe design, a leather upper, contrast sidewall trim, and, of course, a "smiley face" on the toe box. Missing? Generic, just-another-sneaker looks.
Want a tennis shoe you can actually, you know, play tennis in? These K-Swiss UNDFTD Deuce Sneakers ($68) should do the trick. Their unassuming monochrome canvas uppers and white soles make them feel right at home with a pair of jeans and a tee, while the reinforced gum toe cap lets you get in a couple casual games without needing to bust out more specialized gear. Available in black, natural, navy, olive, or the always acceptable white.
Part dress shoe, part chukka, the PF Flyers Drake Sneaker ($90) is perfect for those times when you want to look nice but don't want to take yourself too seriously. Sporting either a brown or black leather upper, the Drake is finished off with gray tristan print lining and a classic PF rubber sole complete with wave tread.