This casual leather sneaker looks great next to jeans or even slacks and has a semi-rigid midsole and a sticky tread pattern to make sure you don’t slip off the pedals. There’s a low-cut version, too, but I prefer the extra height for ankle protection and support. This is no high-tech shoe; it’s called the Joyride because it’s best for light pedaling from home to work and on to the evening’s engagements. (For SPD compatibility, consider these.) Comfy out of the box, durable on the bike, easy on the feet at the bar—what more do you need? $100
Vote for America's Best Town! →
The Cycle Life
Need a Gear Fix?
Open email. Get latest gear. Repeat.